| Journal Articles: 243 results |
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Synthesis of Albendazole Metabolite: Characterization and HPLC Determination Graciela Mahler, Danilo Davyt, Sandra Gordon, Marcelo Incerti, Ivana Núñez, Horacio Pezaroglo, Laura Scarone, Gloria Serra, Mauricio Silvera, and Eduardo Manta
In this laboratory activity, students are introduced to the synthesis of an albendazole metabolite obtained by a sulfide oxidation reaction. Albendazole as well as its metabolite, albendazole sulfoxide, are used as anthelmintic drugs. The oxidation reagent is H2O2 in acetic acid. The reaction is environmental friendly, fast, and proceeds with high yield. The crude reaction is analyzed by HPLC chromatography to determine purity. The simplicity of the experiment allows students to study chiral concepts, physicochemical and spectroscopic properties of the compounds, and HPLC determinations.
Mahler, Graciela; Davyt, Danilo; Gordon, Sandra; Incerti, Marcelo; Núñez, Ivana; Pezaroglo, Horacio; Scarone, Laura; Serra, Gloria; Silvera, Mauricio; Manta, Eduardo. J. Chem. Educ. 2008, 85, 1652.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
HPLC |
Medicinal Chemistry |
Organosulfur Compounds |
Oxidation / Reduction |
Synthesis
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A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas
Describes a one-pot, enantioselective, Robinson annulation geared towards the second-year organic chemistry major and demonstrating aspects of green chemistry.
Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1531.
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Gas Chromatography |
HPLC |
NMR Spectroscopy |
Synthesis |
Green Chemistry
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Frank Westheimer's Early Demonstration of Enzymatic Specificity Addison Ault
Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules.
Ault, Addison. J. Chem. Educ. 2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
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The Resolution of Ibuprofen, 2-(4′-Isobutylphenyl)propionic Acid James V. McCullagh
In this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-a-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments.
McCullagh, James V. J. Chem. Educ. 2008, 85, 941.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enantiomers |
Quantitative Analysis |
Separation Science
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The Same and Not the Same: Chirality, Topicity, and Memory of Chirality Wolfgang H. Kramer and Axel G. Griesbeck
Describes a simple molecular approach that aids students in learning stereochemical terms, definitions, and concepts, particularly when chemical structures are drawn in two dimensions.
Kramer, Wolfgang H.; Griesbeck, Axel G. J. Chem. Educ. 2008, 85, 701.
Chirality / Optical Activity |
Stereochemistry
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Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines Damian A. Allen, Anthony E. Tomaso, Jr., Owen P. Priest, David F. Hindson, and Jamie L. Hurlburt
In this experiment, teams of students are given an optically-pure amine of known structure but unknown stereochemistry. Different teams derivatize samples of the amine with (R) and (S) conformations of Mosher's acid chloride. The resulting diastereomers are analyzed by NMR to determine the absolute configuration of the initial, unknown amine.
Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698.
Amides |
Chirality / Optical Activity |
Chromatography |
Diastereomers |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
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A Simple Laboratory Experiment To Determine the Kinetics of Mutarotation of D-Glucose Using a Blood Glucose Meter Carlos E. Perles and Pedro L. O. Volpe
A simple commercial blood glucose meter is used to follow the kinetics of mutarotation of D-glucose in aqueous solution. The results may be compared with those obtained using an automatic polarimeter.
Perles, Carlos E.; Volpe, Pedro L. O. J. Chem. Educ. 2008, 85, 686.
Aqueous Solution Chemistry |
Bioanalytical Chemistry |
Carbohydrates |
Chirality / Optical Activity |
Enzymes |
Kinetics |
Solutions / Solvents |
Stereochemistry
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The Meaning of Meso Addison Ault
The original use of the prefix "meso" was to refer to an optically inactive, non-resolvable member of a set of stereoisomers, some of which were optically active.
Ault, Addison. J. Chem. Educ. 2008, 85, 441.
Chirality / Optical Activity |
Stereochemistry
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A Simple Method for Drawing Chiral Mononuclear Octahedral Metal Complexes Aminou Mohamadou and Arnaud Haudrechy
This article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties.
Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ. 2008, 85, 436.
Asymmetric Synthesis |
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements
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Can a Non-Chiral Object Be Made of Two Identical Chiral Moieties? Jean François LeMaréchal
Uses the cut of an apple to show that the association of identical chiral moieties can form a non-chiral object.
LeMaréchal, Jean François. J. Chem. Educ. 2008, 85, 433.
Chirality / Optical Activity |
Coordination Compounds |
Enantiomers |
Group Theory / Symmetry |
Stereochemistry |
Transition Elements
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Collection of Chrial Drug, Pesticide, and Fragrance Molecular Models William F. Coleman
This months Featured Molecules include (S)-citalopram, (S,S)-ethambutol, (R)-cetirizine, (S)-sulpiride, (R)-mecoprop, (S,M)-metolachlor, (R)-metalaxyl, (S,P)-metolachior, indoxacarb, (R)-lilial, (4S,7R)-galaxolide, (R)-1-p-menthene-8-ol, R-1-p-menthene-8-thiol, and enantiomers of these structures.
Coleman, William F. J. Chem. Educ. 2007, 84, 2018.
Molecular Modeling |
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
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Unequal Activities of Enantiomers via Biological Receptors: Examples of Chiral Drug, Pesticide, and Fragrance Molecules Albrecht Mannschreck, Roland Kiesswetter, and Erwin von Angerer
Proposes a two-hour lecture intended for medicinal chemistry students that emphasizes the similarity between the different types of receptor-mediated actions of enantiomers which serve as the basis for the actions of chiral drug, pesticide, and fragrance molecules.
Mannschreck, Albrecht; Kiesswetter, Roland; von Angerer, Erwin. J. Chem. Educ. 2007, 84, 2012.
Agricultural Chemistry |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enantiomers |
Medicinal Chemistry |
Receptors |
Stereochemistry
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Showing Enantiomorphous Crystals of Tartaric Acid Julio Andrade-Gamboa
Most drawings of enantiomorphous crystals are inadequate to demonstrate that they are non-superimposable mirror images. This article examines the classic case of tartaric acid and the use of an alternative graphical representation and a paper model to facilitate the conceptualization of this subject.
Andrade-Gamboa, Julio. J. Chem. Educ. 2007, 84, 1783.
Chirality / Optical Activity |
Crystals / Crystallography |
Enantiomers |
Stereochemistry
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Synthesis of Anomeric Methyl Fructofuranosides and Their Separation on an Ion-exchange Resin Erkki Nurminen, Päivi Poijärvi, Katja Koskua, and Jari Hovinen
Treatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl--d-fructopyranoside, methyl-a-D-fructofuranoside, and methyl--d- fructofuranoside, which are separated on an ion exchange column and characterized polarimetrically.
Nurminen, Erkki; Poijärvi, Päivi; Koskua, Katja; Hovinen, Jari. J. Chem. Educ. 2007, 84, 1480.
Carbocations |
Chirality / Optical Activity |
Chromatography |
Ion Exchange |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
Carbohydrates
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Synthesis and NMR Spectral Analysis of Amine Heterocycles: The Effect of Asymmetry on the 1H and 13C NMR Spectra of N,O-Acetals Shahrokh Saba, James A. Ciaccio, Jennifer Espinal, and Courtney E. Aman
Describe an undergraduate organic laboratory experiment in which students prepare two N,O-acetals that differ only in a single ring substituent that introduces asymmetry, giving each compound a distinct 1H and 13C NMR spectral pattern that must be explained by students.
Saba, Shahrokh; Ciaccio, James A.; Espinal, Jennifer; Aman, Courtney E. J. Chem. Educ. 2007, 84, 1011.
Amines / Ammonium Compounds |
Chirality / Optical Activity |
Green Chemistry |
Heterocycles |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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Nuclear Overhauser Effect Spectroscopy. An Advanced Undergraduate Experiment Michael T. Huggins and Freida Billimoria
Describes an advanced laboratory experiment in which students prepare a set of compounds to study both the configuration of a newly formed double bond (E or Z) and the conformation of the molecule.
Huggins, Michael T.; Billimoria, Freida. J. Chem. Educ. 2007, 84, 471.
Alkenes |
Conformational Analysis |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Molecular Properties / Structure |
Chirality / Optical Activity
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Isolation of Three Components from Spearmint Oil: An Exercise in Column and Thin-Layer Chromatography Don R. Davies and Todd M. Johnson
In this exercise, the three major components of spearmint oil, (+)-limonene, L-(-)-carvone, and (1R,2R,4R)-dihydrocarveol, are separated by silica gel column chromatography. The separation is monitored by thin-layer chromatography, and IR analysis is employed to verify the identity of the separated components.
Davies, Don R.; Johnson, Todd M. J. Chem. Educ. 2007, 84, 318.
Chirality / Optical Activity |
Chromatography |
Natural Products |
Microscale Lab |
Thin Layer Chromatography |
Separation Science
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Dynamic Stereochemistry: A Simple Approach To Delineating Relative Configuration Dipak K. Mandal
A simple approach is presented for delineating relative stereochemistry of the product in reactions involving stereogenic center(s).
Mandal, Dipak K. J. Chem. Educ. 2007, 84, 274.
Chirality / Optical Activity |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry
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A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory George D. Bennett
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment also illustrates a number of principles and trade-offs of green chemistry.
Bennett, George D. J. Chem. Educ. 2006, 83, 1871.
Addition Reactions |
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Green Chemistry |
Mechanisms of Reactions |
Stereochemistry
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Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
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Chemical Aspects of General Anesthesia: Part II. Current Practices Robert Brunsvold and Daryl L. Ostercamp
With the basic elements of balanced general anesthesia in place by the 1950s, the focus turned to developing safer and more effective agents and to improving procedures. During the last half-century a new generation of intravenous induction anesthetics, inhalational anesthetics, and muscle relaxants has emerged.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1826.
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
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Chemical Aspects of General Anesthesia: Part I. From Ether to Halothane Robert Brunsvold and Daryl L. Ostercamp
Summarizes general anesthesia from 1846 to 1956. Events leading up to the adoption of a "balanced" approach, where a sequence of individual compounds is used rather than a single agent, are described.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1821.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
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Chemical Aspects of Local and Regional Anesthesia Robert Brunsvold and Daryl L. Ostercamp
The chemistry that underlies the development of local and regional anesthesia is explored. Emphasis is placed upon the importance of acidity constants and lipophilic versus hydrophilic character in interpreting what affect a particular compound has upon biological processes.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1816.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis |
Applications of Chemistry
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Precision in Stereochemical Terminology LeRoy G. Wade, Jr.
This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.
Wade, LeRoy G., Jr. J. Chem. Educ. 2006, 83, 1793.
Chemical Technicians |
Diastereomers |
Enantiomers |
Stereochemistry |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
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Asymmetric Aldol Reaction Induced by Chiral Auxiliary Jorge Pereira and Carlos A. M. Afonso
Describes an asymmetric aldol reaction based on the use of (4R,5S)-1,5-dimethyl-4-phenylimidazolidin- 2-one as a chiral auxiliary in a three-step procedure.
Pereira, Jorge; Afonso, Carlos A. M. J. Chem. Educ. 2006, 83, 1333.
Aldehydes / Ketones |
Asymmetric Synthesis |
Chirality / Optical Activity |
Diastereomers |
NMR Spectroscopy |
Chromatography |
Synthesis |
Stereochemistry
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The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. An Advanced Undergraduate Project in Organic Synthesis and Structural Analysis Lionel Delaude, Jean Grandjean, and Alfred F. Noels
The Robinson annulation is a three-step process involving a Michael addition followed by an internal aldol condensation and a dehydration. It is possible to stop the reaction after every step and to isolate the three products, allowing students to confirm the validity of the stepwise mechanism and develop a more thorough understanding of the whole process.
Delaude, Lionel; Grandjean, Jean; Noels, Alfred F. J. Chem. Educ. 2006, 83, 1225.
Catalysis |
Chirality / Optical Activity |
Conformational Analysis |
Diastereomers |
IR Spectroscopy |
Synthesis |
NMR Spectroscopy |
Stereochemistry
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Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
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Caught on Tape: Catalyst Recovery; Secondary Structure Switch; DNA-Based Chiral Catalysts Angela G. King
Common lab tape aids catalyst delivery and recovery, DNA lends its chirality to organic reaction, and a model for studying the transformation of ahelices to ?sheets.
King, Angela G. J. Chem. Educ. 2006, 83, 10.
Catalysis |
Chirality / Optical Activity |
Proteins / Peptides |
Molecular Modeling |
Molecular Properties / Structure
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Cotton Effect in Copper–Proline Complexes in the Visible Region Victor Volkov and Rolf Pfister
This article suggests taking advantage of the visible dd electronic transition of Cu2+, which allows one to contrast the normal optical rotatory dispersion response of d- and l-proline in aqueous solution with the strong Cotton effect observed when these amino acids are complexed with a metal cation.
Volkov, Victor; Pfister, Rolf. J. Chem. Educ. 2005, 82, 1663.
Chirality / Optical Activity |
IR Spectroscopy |
Molecular Properties / Structure |
Spectroscopy |
Stereochemistry |
UV-Vis Spectroscopy |
Amino Acids |
Coordination Compounds |
Crystal Field / Ligand Field Theory
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Monoterpene Unknowns Identified Using IR, 1H-NMR, 13C-NMR, DEPT, COSY, and HETCOR Lisa T. Alty
This set of NMR experiments can be a capstone experience for a spectroscopy or advanced laboratory course following organic chemistry. Students are given a monoterpene to identify using IR, 1H-NMR, 13C-NMR, and DEPT data. Once the unknown is identified, they can fully interpret and assign each carbon and each proton signal to the structure using COSY and HETCOR along with the one-dimensional NMR data. The rigidity of the ring systems and the chiral centers in all of the compounds present diastereotopic hydrogens and, in some cases, diastereotopic methyl groups.
Alty, Lisa T. J. Chem. Educ. 2005, 82, 1387.
Natural Products |
NMR Spectroscopy |
Diastereomers |
Chirality / Optical Activity |
IR Spectroscopy |
Undergraduate Research
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Synthesis and Physical Properties of Liquid Crystals: An Interdisciplinary Experiment Gerald R. Van Hecke, Kerry K. Karukstis, Hanhan Li, Hansford C. Hendargo, Andrew J. Cosand, and Marja M. Fox
This experiment features an investigative approach designed for the introductory science or engineering major and integrates concepts in the fields of chemistry, biology, and physics. Derived from faculty research interests, this novel experiment gives students the opportunity to draw conclusions from tests performed to illustrate the connection between molecular structure and macroscopic properties. The chemical synthesis of the compounds studied further enhances the connection between molecular structure and macroscopic physical properties. The results of two separate physical measurements, refractometry and absorption spectroscopy, are combined to calculate a microscopic, but very practical, property of chiral nematic liquidsthe pitch of the helix formed in the liquid crystalline phase.
Van Hecke, Gerald R.; Karukstis, Kerry K.; Li, Hanhan; Hendargo, Hansford C.; Cosand, Andrew J.; Fox, Marja M. J. Chem. Educ. 2005, 82, 1349.
Chirality / Optical Activity |
Crystals / Crystallography |
Molecular Properties / Structure |
UV-Vis Spectroscopy |
Acids / Bases |
Esters |
Physical Properties |
Physical Properties
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An Engaging Illustration of the Physical Differences among Menthol Stereoisomers Edward M. Treadwell and T. Howard Black
The differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (-)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed.
Treadwell, Edward M.; Black, T. Howard. J. Chem. Educ. 2005, 82, 1046.
Chirality / Optical Activity |
Stereochemistry |
Thin Layer Chromatography |
Diastereomers |
Enantiomers |
Physical Properties
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Chiral Crystallization of Ethylenediamine Sulfate Lawrence Koby, Jyothi B. Ningappa, Maria Dakessian, and Louis A. Cuccia
Optimized conditions for the chiral crystallization of ethylenediamine sulfate, which can serve as an ideal undergraduate experiment, are described. Large, flat, colorless crystals of ethylenediamine sulfate are obtained in an undisturbed evaporation dish within a period of approximately five to seven days. The crystals are ideal for polarimetry studies and observation using Polaroid sheets. Students become familiar with polarizing filters and how they can be used to distinguish between dextrorotatory and levorotatory crystals.
Koby, Lawrence; Ningappa, Jyothi B.; Dakessian, Maria; Cuccia, Louis A. J. Chem. Educ. 2005, 82, 1043.
Chirality / Optical Activity |
Crystals / Crystallography |
Stereochemistry |
Physical Properties
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Enantiomeric Resolution of (±)-Mandelic Acid by (1R,2S)-(–)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism Marsha R. Baar and Andrea L. Cerrone-Szakal
There has been an increasing need, particularly in the pharmaceutical industry, to prepare chiral substances in single-isomer form. A chiral technique that makes an excellent introductory organic chemistry experiment is enantiomeric resolution. The classical resolution of ()-mandelic acid using the chiral amine, (1R,2S)-()-ephedrine, was adapted for use in introductory organic chemistry lab curricula.
Baar, Marsha R.; Cerrone-Szakal, Andrea L. J. Chem. Educ. 2005, 82, 1040.
Acids / Bases |
Chirality / Optical Activity |
Separation Science |
Stereochemistry |
Diastereomers |
Enantiomers
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Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands Albrecht Mannschreck and Roland Kiesswetter
The following practical applications of the formation of two diastereomeric association complexes that may differ with respect to their physical and chemical properties are briefly described: the small- and large-scale preparation of the enantiomers of organic compounds; the analysis of chiral nonracemic mixtures by chromatography and by NMR spectroscopy; and the growing use of drugs in the form of one of the enantiomers. It is proposed to emphasize the similarity of the association-based differentiations.
Mannschreck, Albrecht; Kiesswetter, Roland. J. Chem. Educ. 2005, 82, 1034.
Chirality / Optical Activity |
Noncovalent Interactions |
Stereochemistry |
Bioorganic Chemistry |
Chromatography |
Enantiomers |
Medicinal Chemistry |
NMR Spectroscopy |
Precipitation / Solubility |
Receptors |
Molecular Properties / Structure
|
Stereogenic Centers and Axes: A Comparison of the Chiral Topologies Available to Cabcd and abC=C=Ccd Paul Lloyd-Williams and Ernest Giralt
In this article we provide a comparative analysis of molecular chirality as a consequence of the presence of stereogenic centers and axes. We have found this to be a useful and informative classroom exercise that helps to put some of the most important stereochemical principles on a firmer footing. Chirality in molecules incorporating a stereogenic center can be fully explained using the regular tetrahedron as a model. Analysis of chirality in molecules incorporating a stereogenic axis, on the other hand, requires the use of a less regular, stretched or extended, tetrahedron. The key difference between the two types of molecule is the number of chiral topologies available to each.
Lloyd-Williams, Paul; Giralt, Ernest. J. Chem. Educ. 2005, 82, 1031.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry
|
Chirality Made Simple: A 1- and 2-Dimensional Introduction to Stereochemistry Robert E. Gawley
Using internal and external reflection elements in one-, two-, and three-dimensional space, the concept of chirality can be introduced in simple terms that are readily understood. Illustrations of 2-D chirality include block letters of the alphabet and the popular video game Tetris. The concepts of 3-D chirality follow logically and can be simplified by projection back to 2-D. Several examples are given, and a PowerPoint presentation of the concepts is available in the Supplemental Material.
Gawley, Robert E. J. Chem. Educ. 2005, 82, 1009.
Chirality / Optical Activity |
Group Theory / Symmetry |
Stereochemistry |
Enantiomers
|
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory Christopher J. Nichols and Melissa R. Taylor
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005, 82, 105.
Chirality / Optical Activity |
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Alkenes |
Addition Reactions
|
Synthesis and Resolution of the Atropisomeric 1,1'-Bi-2-naphthol: An Experiment in Organic Synthesis and 2-D NMR Spectroscopy Kendrew K. W. Mak
The synthesis and resolution of the atropisomeric 1,1'-bi-2-naphthol illustrates several important concepts in organic chemistry and serves as a good experiment for organic chemistry laboratory course of intermediate to advanced levels. Racemic 1,1'-bi-2-naphthol is synthesized by the oxidative coupling of 2-naphthol and is resolved into the enantiopure form by the selective inclusion compound formation of the R enantiomer with (-)-N-benzylcinchonidinium chloride. The enantiomeric excess of the products are determined by chiral HPLC.
Mak, Kendrew K. W. J. Chem. Educ. 2004, 81, 1636.
Chromatography |
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
A Simple Illustration of Hemihedral Faces Addison Ault
A pair of blocks is described that illustrate exactly the enantiomeric relationship that led Pasteur to the concept of molecular chirality. The blocks are enantiomeric and have C2 symmetry.
Ault, Addison. J. Chem. Educ. 2004, 81, 1605.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
Demonstration of Enantiomer Specificity of Proteins and Drugs Gretchen L. Anderson
In addition to the traditional use of molecular models of tetrahedral asymmetric centers, the concept of chirality and its importance to proteindrug interactions is demonstrated in a guided classroom activity.
Anderson, Gretchen L. J. Chem. Educ. 2004, 81, 971.
Enantiomers |
Proteins / Peptides |
Drugs / Pharmaceuticals |
Enzymes |
Chirality / Optical Activity
|
The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment Victor Cesare, Ishwar Sadarangani, Janet Rollins, and Dennis Costello
This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic of carboxylic acid derivatives into the organic chemistry laboratory.
Cesare, Victor; Sadarangani, Ishwar; Rollins, Janet; Costello, Dennis. J. Chem. Educ. 2004, 81, 713.
Synthesis |
Chirality / Optical Activity |
NMR Spectroscopy
|
The Monosodium Glutamate Story: The Commercial Production of MSG and Other Amino Acids Addison Ault
Examples of the industrial synthesis of pure amino acids are presented. The emphasis is on the synthesis of (S)-glutamic acid and, to a lesser extent, (S)-lysine and (R,S)-methionine. These amino acids account for about 90% of the total world production of amino acids.
Ault, Addison. J. Chem. Educ. 2004, 81, 347.
Amino Acids |
Biotechnology |
Chirality / Optical Activity |
Consumer Chemistry |
Enzymes |
Natural Products |
Stereochemistry |
Synthesis |
Food Science
|
Vibrational Analysis for C60 and Other Fullerenes Frank Rioux
Nakamoto and McKinney provided a symmetry analysis of the vibrational modes of C60 and other fullerenes. I would like to supplement their presentation with another approach, in widespread use, which records the number of atoms that are unmoved by each symmetry operation, yielding the reducible representation Guma.
Rioux, Frank. J. Chem. Educ. 2003, 80, 1380.
Chirality / Optical Activity |
Group Theory / Symmetry |
IR Spectroscopy |
NMR Spectroscopy |
Raman Spectroscopy |
Alkenes
|
Vibrational Analysis for C60 and Other Fullerenes Frank Rioux
Nakamoto and McKinney provided a symmetry analysis of the vibrational modes of C60 and other fullerenes. I would like to supplement their presentation with another approach, in widespread use, which records the number of atoms that are unmoved by each symmetry operation, yielding the reducible representation Guma.
Rioux, Frank. J. Chem. Educ. 2003, 80, 1380.
Chirality / Optical Activity |
Group Theory / Symmetry |
IR Spectroscopy |
NMR Spectroscopy |
Raman Spectroscopy |
Alkenes
|
Desymmetrization of the Tetrahedron: Stereogenic Centers Paul Lloyd-Williams and Ernest Giralt
While the regular tetrahedron is the more straightforward model and is preferable for rationalizing stereochemistry at the undergraduate level for molecules containing stereogenic centers , it is important that both the instructor and students be fully aware that the tetrahedral model represents a simplification and that the use of irregular tetrahedra would be physically more realistic.
Lloyd-Williams, Paul; Giralt, Ernest. J. Chem. Educ. 2003, 80, 1178.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry
|
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
|
Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets Ryan G. Stabile and Andrew P. Dicks
Procedure for synthesis of the active ingredient in many well-known, over-the-counter cough syrups - 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 313.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Mathematics / Symbolic Mathematics |
Microscale Lab |
Synthesis |
Stereochemistry |
Applications of Chemistry |
Ethers |
Aromatic Compounds |
Medicinal Chemistry
|
The World's First "Pastarimeter": An Analogous Demonstration of Polarimetry Using Pasta Fusilli Claire Saxon, Scott Brindley, Nic Jervis, Graeme R. Jones, E. David Morgan, and Christopher A. Ramsden
Demonstration in which clockwise pasta in one glass tube causes exiting water to rotate in that direction while counter clockwise pasta in a second tube has the opposite effect.
Saxon, Claire; Brindley, Scott; Jervis, Nic; Jones, Graeme R.; Morgan, E. David; Ramsden, Christopher A. J. Chem. Educ. 2002, 79, 1214.
Chirality / Optical Activity |
Stereochemistry
|
Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone by Sodium Borohydride and Baker's Yeast Nicola Pohl, Allen Clague, and Kimberly Schwarz
Students compare biological and chemical means of introducing chirality into a molecule by investigating the reduction of a ketoester with two different reducing agents.
Pohl, Nicola; Clague, Allen; Schwarz, Kimberly. J. Chem. Educ. 2002, 79, 727.
Chirality / Optical Activity |
Oxidation / Reduction |
Synthesis |
Green Chemistry
|
Experiments with Tris(ethylenediamine)cobalt(III) Compounds: 59Co NMR and the Resolution of Enantiomeric [Co(en)3] 3+ Ion and Analysis by Formation of Diastereomeric Ion Pairs L. L. Borer, J. G. Russell, R. E. Settlage, and R. G. Bryant
Using a cobalt(III) compound to illustrate techniques in coordination chemistry.
Borer, L. L.; Russell, J. G.; Settlage, R. E.; Bryant, R. G. J. Chem. Educ. 2002, 79, 494.
Chirality / Optical Activity |
Coordination Compounds |
NMR Spectroscopy |
Diastereomers |
Enantiomers |
Synthesis |
Molecular Properties / Structure
|
"Dishing Out" Stereochemical Principles Harold Hart
Demonstrating the concepts of chiral centers and enantiomers using plastic dishes.
Hart, Harold. J. Chem. Educ. 2001, 78, 1632.
Chirality / Optical Activity |
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Enantiomers
|
Using Guided Inquiry to Study Optical Activity and Optical Rotatory Dispersion in a Cross-Disciplinary Chemistry Lab Michael A. Vaksman and James W. Lane
Procedure in which students are challenged to measure the angle optical rotation at a particular wavelength for an optically active sample.
Vaksman, Michael A.; Lane, James W. J. Chem. Educ. 2001, 78, 1507.
Chirality / Optical Activity |
Lasers |
Spectroscopy |
Stereochemistry
|
Demonstrating Chirality: Using a Mirror with Physical Models to Show Non-superimposability of Chiral Molecules with Their Mirror Images Michael J. Collins
Using a mirror with physical models to show non-superimposability of chiral molecules with their mirror images.
Collins, Michael J. J. Chem. Educ. 2001, 78, 1484.
Chirality / Optical Activity |
Enantiomers |
Molecular Modeling |
Molecular Properties / Structure
|
Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory John Hanson
Laboratory series to introduce students to an important synthetic method and many common techniques used in running reactions, purifying products, and characterizing compounds.
Hanson, John. J. Chem. Educ. 2001, 78, 1266.
Catalysis |
Chirality / Optical Activity |
Synthesis |
Organometallics |
Stereochemistry |
Epoxides |
Enantiomers |
Aromatic Compounds
|
On Chirality in Substituted Metallocenes Bearing Identical Substituents Daisy de Brito Rezende and Ivan P. de Arruda Campos
Analysis of planar chirality in substituted metallocenes.
Rezende, Daisy de Brito; Campos, Ivan P. de Arruda. J. Chem. Educ. 2001, 78, 1130.
Chirality / Optical Activity |
Organometallics |
Stereochemistry |
Molecular Properties / Structure
|
A Simple Solution for Leaking Polarimeter Cells Gene A. Hiegel
Polarimeter cell windows can be coated with a solution of silicone oil to prevent the cells from leaking.
Hiegel, Gene A. J. Chem. Educ. 2001, 78, 648.
Chirality / Optical Activity |
Laboratory Equipment / Apparatus |
Laboratory Management
|
Introducing Stereochemistry to Non-science Majors Hannia Luján-Upton
Two exercises to introduce concepts associated with stereochemistry such as "sameness", superimposability, chirality, enantiomers, optical activity, polarimetry, and racemic mixtures; one compares chirality in hands with the achiral nature of two textbooks, the other involves a murder mystery.
Luján-Upton, Hannia. J. Chem. Educ. 2001, 78, 475.
Chirality / Optical Activity |
Stereochemistry |
Nonmajor Courses |
Molecular Properties / Structure
|
Solvent Swelling Demonstrations: Possible Extension to Other Types of Material (about J. Chem. Educ. 2000, 77, 876-878) D. J. Campbell, E. R. Freidinger, and Carl Murphy
Demonstrating solvent-induced swelling using pasta, rubber bands, silicone caulk, and superabsorbent polymer powder.
Campbell, D. J.; Freidinger, E. R.; Murphy, Carl. J. Chem. Educ. 2001, 78, 165.
Chirality / Optical Activity |
Transport Properties |
Solutions / Solvents
|
Solvent Swelling Demonstrations: Possible Extension to Other Types of Material (about J. Chem. Educ. 2000, 77, 876-878) J. C. Jones
Demonstrating the solvent-induced swelling of rank coal (lignite).
Jones, J. C. J. Chem. Educ. 2001, 78, 165.
Chirality / Optical Activity |
Transport Properties |
Solutions / Solvents |
Geochemistry
|
Solvent Swelling Demonstrations: Possible Extension to Other Types of Material (about J. Chem. Educ. 2000, 77, 876-878) J. C. Jones
Demonstrating the solvent-induced swelling of rank coal (lignite).
Jones, J. C. J. Chem. Educ. 2001, 78, 165.
Chirality / Optical Activity |
Transport Properties |
Solutions / Solvents |
Geochemistry
|
Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory Christopher S. Callam and Todd L. Lowary
Experiment to give students additional exposure to carbohydrate chemistry and provide an opportunity to discuss kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 73.
Carbohydrates |
Medicinal Chemistry |
NMR Spectroscopy |
Synthesis |
Kinetics |
Esters |
Diastereomers |
Chirality / Optical Activity |
Alcohols
|
Solvent Swelling and Optical Rotation Demonstrated on the Overhead Projector Dean J. Campbell and Sarah B. Rupe
Reversible solvent swelling of the transparent elastomer polydimethylsiloxane (PDMS) with organic solvents can be shown on an overhead projector. Use of optically active solvents such as the (R)-(+) and (S)-(-) enantiomers of limonene results in the solvent-swollen slab of PDMS having optical activity.
Campbell, Dean J.; Rupe, Sarah B. J. Chem. Educ. 2000, 77, 876.
Chirality / Optical Activity |
Transport Properties |
Solutions / Solvents
|
Application of the Correlation Method to Vibrational Spectra of C60 and Other Fullerenes: Predicting the Number of IR- and Raman-Active Bands Kazuo Nakamoto and Michael A. McKinney
The C60 molecule (Buckyball/soccer ball) exhibits only 4 IR and 10 Raman bands although it possesses 174 (3 x 60 - 6) normal vibrations. This striking reduction in the number of observed bands is evidently due to the molecule's extremely high symmetry (Ih point group).
Nakamoto, Kazuo; McKinney, Michael A. J. Chem. Educ. 2000, 77, 775.
Chirality / Optical Activity |
Group Theory / Symmetry |
IR Spectroscopy |
NMR Spectroscopy |
Raman Spectroscopy |
Molecular Properties / Structure |
Molecular Modeling
|
Enantiomeric and Diastereoisomeric Relationships: A Practical Approach V. Durieu, G. Martiat, M. Ch. Vandergeten, F. Pirsoul, F. Toubeau, and Agnès Van Camp
An experiment in organic chemistry in which the students prepare, purify, and characterize optical isomers. The three optical isomers of the bisoxalamides obtained by the reaction of racemic 1-phenylethylamine with diethyloxalate are separable by flash chromatography into the racemic mixture of (R,R) + (S,S) oxalamides and the (R,S) meso compound.
Durieu, V.; Martiat, G.; Vandergeten, M. Ch.; Pirsoul, F.; Toubeau, F.; Van Camp, Agnès. J. Chem. Educ. 2000, 77, 752.
Molecular Properties / Structure |
Stereochemistry |
Separation Science |
Enantiomers |
Diastereomers |
Chirality / Optical Activity |
Synthesis
|
Introducing Chiroscience into the Organic Laboratory Curriculum Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
|
Applications of Biocatalysis to Industrial Processes John T. Sime
The possibility of environmentally friendly chemical reactions carried out under mild conditions with high degrees of selectivity has proved attractive in developing manufacturing processes. A number of such reactions are discussed in the industrial context with examples of a variety of reaction types. All processes presented have been implemented in the production of commercial products and provide a feel for the versatility of this technology.
Sime, John T. J. Chem. Educ. 1999, 76, 1658.
Biotechnology |
Catalysis |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enzymes |
Proteins / Peptides |
Synthesis |
Industrial Chemistry |
Applications of Chemistry |
Amides |
Esters
|
Resolution of trans-Cyclohexane-1,2-diamine and Determination of the Enantiopurity Using Chiral Solid-Phase HPLC Techniques and Polarimetry Patrick J. Walsh, Diane K. Smith, and Chris Castello
The experiment is designed to reinforce and broaden the students' understanding of the relationship between enantiomers and diasteriomers and of diasteriomeric interactions. Additionally, it illustrates the differences in physical properties (solubility and melting range) between a racemic mixture and the same compound in highly resolved form.
Walsh, Patrick J.; Smith, Diane K.; Castello, Chris. J. Chem. Educ. 1998, 75, 1459.
Chromatography |
Synthesis |
Separation Science |
Stereochemistry |
HPLC |
Alkanes / Cycloalkanes |
Amines / Ammonium Compounds |
Chirality / Optical Activity
|
Resolution of Racemic Phenylsuccinic Acid Using (-)-Proline as a Resolving Agent: An Introductory Organic Chemistry Experiment Victor Cesare and Ralph Stephani
Isolation of the (+)-enantiomer can be completed in about two hours and this procedure can also be used to introduce the reflux and recrystallization techniques.
Cesare, Victor; Stephani, Ralph. J. Chem. Educ. 1997, 74, 1226.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
An Example of a Human Topological Rubber Glove Act Yock Chai Toong and Shih Yung Wang
A hitherto unreported human body narcissistic inversion which is an example of the rubber glove act has been uncovered from a Chinese acrobatic performance. This inversion is related to the unimolecular enantiomerizations of chiral molecules, a topological figure and a rubber glove via chiral pathway.
Toong, Yock Chai; Wang, Shih Yung. J. Chem. Educ. 1997, 74, 403.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Aromatic Compounds
|
When Drug Molecules Look in the Mirror Edwin Thall
Enantiomers possess virtually identical physical properties but often display very different biological activities. Stereochemical non-equivalence, chiral recognition, enantiomer uniqueness, and the preparation of optically active drugs are reviewed.
Thall, Edwin. J. Chem. Educ. 1996, 73, 481.
Enantiomers |
Stereochemistry |
Drugs / Pharmaceuticals |
Chirality / Optical Activity
|
ORD through the Eyes of Mathematica Novak, Igor
180. Bits and pieces, 55. Using Mathematica to illustrate the ORD phenomena.
Novak, Igor J. Chem. Educ. 1995, 72, 1084.
Chirality / Optical Activity |
Mathematics / Symbolic Mathematics
|
A Straightforward Method for Assigning Stereochemical Lambda/Delta Descriptors to Octahedral Coordination Compounds Santiago Herrero and Miguel Angel Usón
A straightforward method for assigning stereochemical ?/? descriptors to octahedral coordination compounds.
Herrero, Santiago; Uson, Miguel Angel. J. Chem. Educ. 1995, 72, 1065.
Stereochemistry |
Molecular Properties / Structure |
Coordination Compounds |
Chirality / Optical Activity
|
NMR Spectroscopy Using a Chiral Lanthanide Shift Reagent to Assess the Optical Purity of 1-Phenylethylamine Tito Viswanathan and Alan Toland
An experiment to exemplify the use of NMR in determining the resolution of a racemic mixture separation.
Viswanathan, Tito; Toland, Alan. J. Chem. Educ. 1995, 72, 945.
NMR Spectroscopy |
Chirality / Optical Activity |
Stereochemistry |
Separation Science |
Amines / Ammonium Compounds
|
Chiroptical Spectroscopy Jerome E. Gurst
Use of chiroptical spectroscopy to assign absolute or relative configurations and in conformational analysis.
Gurst, Jerome E. J. Chem. Educ. 1995, 72, 827.
Chirality / Optical Activity |
Stereochemistry |
Conformational Analysis
|
The Conformational Behavior of n-Pentane: A Molecular Mechanics and Molecular Dynamics Experiment Mencarelli, Paolo
174. Use of HyperChem to investigate the conformational behavior of n-pentane.
Mencarelli, Paolo J. Chem. Educ. 1995, 72, 511.
MO Theory |
Chirality / Optical Activity |
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Molecular Mechanics / Dynamics |
Molecular Modeling
|
Steric Hindrance by Bromination of Alkylbenzenes: Experimental Demonstration Cooley, James H.; Abobaker, Nagib M.
Procedure to illustrate the influence of steric hindrance on organic chemistry in which students must decide what data to collect and how to interpret it.
Cooley, James H.; Abobaker, Nagib M. J. Chem. Educ. 1995, 72, 463.
Molecular Properties / Structure |
Synthesis |
Chirality / Optical Activity |
Aromatic Compounds |
Stereochemistry
|
Chemical Education via MOLGEN Benecke, C.; Grund, R.; Kerber, A.; Laue, R.; Wieland, T.
173. Bits and pieces, 53. Software used to produce all the isomers for a given chemical formula.
Benecke, C.; Grund, R.; Kerber, A.; Laue, R.; Wieland, T. J. Chem. Educ. 1995, 72, 403.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Molecular Modeling
|
Determination of the R or S Configuration of Tetrahedral Stereocenters: A Graphical Flowchart Approach Starkey, Ronald
Using graphical flowcharts to determine R or S configurations through higher shell comparisons for long-chain, highly branched, and cyclic organic structures.
Starkey, Ronald J. Chem. Educ. 1995, 72, 315.
Chirality / Optical Activity |
Molecular Properties / Structure |
Nomenclature / Units / Symbols
|
Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
|
Put the Body to Them! Perkins, Robert R.
Examples of chemistry demonstrations involving student participation, including quantized states and systems, boiling point trends, intermolecular vs. intramolecular changes, polar/nonpolar molecules, enantiomers and diastereomers, and chromatography.
Perkins, Robert R. J. Chem. Educ. 1995, 72, 151.
Chromatography |
Physical Properties |
Phases / Phase Transitions / Diagrams |
Molecular Properties / Structure |
Chirality / Optical Activity |
Quantum Chemistry |
Diastereomers |
Enantiomers
|
Which Organic Molecule Should I Pick? Perkins, Robert
Examples of questions requiring students to demonstrate their understanding of organic structures, nomenclature, isomerism, and chemical reactivity.
Perkins, Robert J. Chem. Educ. 1995, 72, 124.
Molecular Properties / Structure |
Chirality / Optical Activity |
Nomenclature / Units / Symbols |
Enantiomers |
Diastereomers
|
Enantiomeric Separation of Beta-Blockers by High Performance Liquid Chromatography: An Undergraduate Analytical Chemistry Experiment Tran, Chieu D.; Dotlich, Michael
Experimental procedure to familiarize students with the principle and application of high performance liquid chromatography (HPLC) to separate isomers of a common pharmaceutical; includes data and analysis.
Tran, Chieu D.; Dotlich, Michael J. Chem. Educ. 1995, 72, 71.
Chirality / Optical Activity |
Chromatography |
Drugs / Pharmaceuticals |
Separation Science |
HPLC
|
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis
|
Haloallenes: Chiral Compounds without Chiral Carbon Atoms Novak, Igor
Four questions regarding the structure, stereochemistry, and symmetry of haloallenes.
Novak, Igor J. Chem. Educ. 1994, 71, 579.
Chirality / Optical Activity |
Group Theory / Symmetry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
|
Grasping the Concepts of Stereochemistry Barta, Nancy S.; Stille, John R.
An alternative procedure for the determination of R or S configuration for chiral molecules.
Barta, Nancy S.; Stille, John R. J. Chem. Educ. 1994, 71, 20.
Stereochemistry |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
|
Microscale yeast mediated enantiospecific reduction of vanillin, and the absolute configuration of (-)-(R)-[alpha]-deuteriovanillyl alcohol: A bioorganic chemistry experiment Lee, Moses
An experiment is introduced to a sophomore chemistry course that demonstrates the effeciency and enantiospecificity of microbial/enzyme-mediated reactions and the use of NMR methods in determining the optical activity and absolute configuration of chiral alcohols.
Lee, Moses J. Chem. Educ. 1993, 70, A155.
Enantiomers |
Alcohols |
Bioorganic Chemistry |
Chirality / Optical Activity |
NMR Spectroscopy |
Microscale Lab
|
Transformation of chemistry experiments into real world contexts Bayer, Richard; Hudson, Bud; Schneider, Jane
Some background on the importance of using lasers to teach concepts in general chemistry and examples of demonstrations under development.
Bayer, Richard; Hudson, Bud; Schneider, Jane J. Chem. Educ. 1993, 70, 323.
Lasers |
Chirality / Optical Activity |
Covalent Bonding
|
Structure, chirality, and FT-NMR in sophomore organic chemistry Chapman, Orville L.; Russell, Arlene A.
An experimental approach (NMR) to teaching organic structure.
Chapman, Orville L.; Russell, Arlene A. J. Chem. Educ. 1992, 69, 779.
NMR Spectroscopy |
Fourier Transform Techniques |
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Elimination Reactions
|
The square knot and the granny knot: An analogy for diastereomers. Tavernier, Dirk.
Few of the diastereomorphs generated by joining two man-made chiral objects have different names; the author is aware of just one example - the square knot and the granny knot.
Tavernier, Dirk. J. Chem. Educ. 1992, 69, 627.
Diastereomers |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
|
Symmetry in automobile tires and the left-right problem. Jackson, W. Gregory.
Automobile tires are a fascinating subject for the consideration of symmetry.
Jackson, W. Gregory. J. Chem. Educ. 1992, 69, 624.
Group Theory / Symmetry |
Chirality / Optical Activity
|
Conglomerate crystallization and chiral discrimination phenomena: In vivo and in vitro. Bernal, Ivan.
Unequal amounts of right- and left-handed material are generally formed during conglomerated crystallization experiments.
Bernal, Ivan. J. Chem. Educ. 1992, 69, 468.
Chirality / Optical Activity |
Crystals / Crystallography |
Enantiomers
|
Representing isomeric structures: Five applications. Thall, Edwin.
Five applications of a new method that the author calls Representing Isomeric Structures, in which arrows are used to point to unique sites on the carbon skeleton to represent functional groups.
Thall, Edwin. J. Chem. Educ. 1992, 69, 447.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
|
Determining a chiral molecule's R/S configuration using the rule of multiplication Wang, Jin-Xian; Yang, Chi
The authors have developed a simple, rapid, and general method for specifying the R/S configuration of a stereogenic center.
Wang, Jin-Xian; Yang, Chi J. Chem. Educ. 1992, 69, 373.
Chirality / Optical Activity |
Stereochemistry |
Chemometrics
|
The new method of rapid determination of chiral molecule configuration: The triangle method Yongsheng, Han; Cailan, Wang
This paper describes a new method for applying the Cahn-Ingold-Prelog rules to determine the configuration of a chiral molecule directly from its Fischer projection formula.
Yongsheng, Han; Cailan, Wang J. Chem. Educ. 1992, 69, 273.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Properties / Structure
|
Symmetry elements and molecular achirality Chen, Guo-Qiang
The reliability of a prediction of achirality of a molecule by inspecting a rotating plane of symmetry is ensured by following the demonstration.
Chen, Guo-Qiang J. Chem. Educ. 1992, 69, 159.
Chirality / Optical Activity |
Molecular Properties / Structure
|
Reduction of acetylferrocene with lithium aluminum hydride and resolution of the enantiomers with a chiral HPLC column: An experiment for the advanced undergraduate laboratory Hamilton, Dorothy E.
An experiment for the advanced undergraduate laboratory that looks at the reduction of acetylferrocene with lithium aluminum hydride and resolution of the enantiomers with a chiral HPLC column.
Hamilton, Dorothy E. J. Chem. Educ. 1991, 68, A143.
Grignard Reagents |
HPLC |
Enantiomers |
Chirality / Optical Activity
|
Chiral crackers: A palatable approach to optical isomerism Griffin, Susan F.
Crackers obtained from the grocery store can be used to help students understand enantiomers.
Griffin, Susan F. J. Chem. Educ. 1991, 68, 1029.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
Natural and unnatural models for illustrating chirality at two centers Nave, Paul M.
Some clever suggestions for models that will help students understand chirality better. Puppies and a two-headed goat are involved.
Nave, Paul M. J. Chem. Educ. 1991, 68, 1028.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
Molecular recognition in aqueous solution: Supramolecular complexation and catalysis Diederich, Francois
Structures of cyclophanes and their complexes with organic compounds, cyclophane complexes of aromatic guests in water, complexation of arenes in organic solvents, water-soluble optically active cyclophanes, and catalytic cyclophanes.
Diederich, Francois J. Chem. Educ. 1990, 67, 813.
Molecular Recognition |
Aqueous Solution Chemistry |
Catalysis |
Noncovalent Interactions |
Aromatic Compounds |
Chirality / Optical Activity |
Molecular Properties / Structure
|
Molecular structure and chirality (Author response) Lechner, Joseph H.
When right and left hands are perceived as isolated segments of the body, possessing a mirror-image relationship, with the understanding that they cannot be superimposed, then the true sense of chirality is imparted.
Lechner, Joseph H. J. Chem. Educ. 1990, 67, 358.
Chirality / Optical Activity |
Molecular Properties / Structure
|
Molecular structure and chirality Brand, David J.
The statement that a pair of hands is "chiral" was misleading and would unnecessarily frustrate students.
Brand, David J. J. Chem. Educ. 1990, 67, 358.
Chirality / Optical Activity |
Molecular Properties / Structure
|
Polarized light and rates of chemical reactions Weir, John J.
This experiment provides the opportunity to introduce the principles of reaction kinetics, polarized light, and the chemistry of optically active compounds; the rate of the acid-catalyzed hydrolysis of sucrose to glucose and fructose is determined.
Weir, John J. J. Chem. Educ. 1989, 66, 1035.
Rate Law |
Kinetics |
Chirality / Optical Activity |
Carboxylic Acids
|
A demonstration of the optical activity of a pair of enantiomers Knauer, Bruce
Uses the enantiomers (S)-(+)-carvone and (R)-(-)-carvone and a polarizing sheet to illustrate optical activity.
Knauer, Bruce J. Chem. Educ. 1989, 66, 1033.
Chirality / Optical Activity |
Enantiomers
|
A new philosophy for teaching advanced organic chemistry: Representative laboratory experiment: Stereoselective reduction of a chiral iminium ion Polniaszek, Richard P.
Students are introduced to lithium diisopropylamide (LDA), enolate chemistry, and the field of assymetric synthesis.
Polniaszek, Richard P. J. Chem. Educ. 1989, 66, 970.
Chirality / Optical Activity |
Stereochemistry
|
Change in optical rotation with wavelength Koubek, Edward; Quinn, H.
Illustrates the effect of an optically active material (Karo corn syrup) on plane-polarized light.
Koubek, Edward; Quinn, H. J. Chem. Educ. 1989, 66, 853.
Photochemistry |
Chirality / Optical Activity
|
Why is ammonia not optically active? Kettle, Sidney F. A.
When a translation and rotation transform under the same irreducible representations of a point group, we must expect molecules of that symmetry to be optically active.
Kettle, Sidney F. A. J. Chem. Educ. 1989, 66, 841.
Chirality / Optical Activity |
Group Theory / Symmetry
|
Chiral lanthanide NMR shift reagents and equilibria with substrate enantiomers: Rationale for the observed signals Rothchild, Robert
An analogy illustrating the two chemical equations that describe the simple view of the dynamic equilibria in which two enantiomers of substrate rapidly and reversibly bind to an optically pure lanthanide shift reagent to form two different bound complexes.
Rothchild, Robert J. Chem. Educ. 1989, 66, 814.
Chirality / Optical Activity |
Transition Elements |
NMR Spectroscopy |
Enantiomers
|
A mnemonic device for assignment of pro-R and pro-S descriptors to stereoheterotopic ligands Nasipuri, Dhanonjoy
A simple mnemonic device for assigning configurational descriptors to appropriate ligands in molecules with a prochiral center or centers written in Fischer projection formulas and in molecules with a prochiral axis.
Nasipuri, Dhanonjoy J. Chem. Educ. 1989, 66, 483.
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
|
Absolutely "simple" configuration in Fischer projection formula Reddy, K. R. N.
A table from which one can easily assign the absolute configuration in Fischer projection formula after designating priorities of the substituents directly bonded to the chiral center.
Reddy, K. R. N. J. Chem. Educ. 1989, 66, 480.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry
|
Stereochemistry of cyclic hydrocarbons Perkins, Robert R.
The topic of stereochemistry always poses great difficulties for many students in introductory organic chemistry. The following problems can be used as a tutorial question after having introduced the various terms associated with stereochemistry. The question requires skills at the applications level in the Bloom taxonomy.
Perkins, Robert R. J. Chem. Educ. 1988, 65, 860.
Alkanes / Cycloalkanes |
Chirality / Optical Activity |
Stereochemistry |
Diastereomers |
Constitutional Isomers
|
Rules for determining d,l configurations in Haworth structures Wilson, Jerry L.
This article provides a set of rules for determining the proper stereochemistry of carbohydrates when using Haworth projections that are simple enough for use in a basic biochemistry course.
Wilson, Jerry L. J. Chem. Educ. 1988, 65, 783.
Carbohydrates |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
Optical activity: an improved demonstration Hambly, Gordon F.
This demonstration on optical activity adds to a previously described demonstration making it more impressive and instructive.
Hambly, Gordon F. J. Chem. Educ. 1988, 65, 623.
Chirality / Optical Activity |
Enantiomers
|
Lecture demonstrations for organic/ biochemistry allied health courses Deavor, James P.
Simple demonstrations on enantiomeric pairs and protein structure.
Deavor, James P. J. Chem. Educ. 1988, 65, 622.
Enantiomers |
Chirality / Optical Activity |
Proteins / Peptides |
Nonmajor Courses |
Amino Acids
|
Novel models for illustrating chirality at two centers Feldman, Martin R.
Commercially available cookies can demonstrate chirality.
Feldman, Martin R. J. Chem. Educ. 1988, 65, 580.
Chirality / Optical Activity |
Enantiomers |
Molecular Modeling
|
Organic lecture demonstrations Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
|
Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids (Coopola, Gary M.; Schuster, Herbert F.) Berlin, K. Darrell
Nine chapters, each headed by an amino acid: alanine, phenylalanine, valine, leucine, hydroxy amino acids, sulfur-containing amino acids, difunctional amino acids, proline, and tryptophan.
Berlin, K. Darrell J. Chem. Educ. 1987, 64, A248.
Chirality / Optical Activity |
Synthesis |
Amino Acids
|
Organic Stereochemistry, Review I (Bays, J. Philip) Finzel, Rodney B.
Software intended to cover the concepts of stereochemistry as they are applied to organic molecules.
Finzel, Rodney B. J. Chem. Educ. 1987, 64, A116.
Stereochemistry |
Chirality / Optical Activity |
Enrichment / Review Materials
|
Molecular structure and chirality Brand, David J.; Fisher, Jed
Clarification of the meaning of the term chiral and its application to both chiral and achiral molecules.
Brand, David J.; Fisher, Jed J. Chem. Educ. 1987, 64, 1035.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
An astonishingly easy method for determining R and S for Fischer projections Ruekberg, Benjamin P.
Identifying the absolute configuration of Fischer projections once students have mastered the concept of Cahn-Ingold-Prelog sequencing.
Ruekberg, Benjamin P. J. Chem. Educ. 1987, 64, 1034.
Stereochemistry |
Chirality / Optical Activity
|
Chiral shift reagent analysis of enantioselectivity in baker's yeast reductions of ethyl acetoacetate: An NMR experiment Lipkowitz, K. B.; Mooney, J. L.
A laboratory exercise in which NMR is used to monitor enantiometric excess in assymetric reductions.
Lipkowitz, K. B.; Mooney, J. L. J. Chem. Educ. 1987, 64, 985.
Chirality / Optical Activity |
Enantiomers |
NMR Spectroscopy |
Stereochemistry
|
Some ideas from the past Kolb, Doris, editor
Demonstrations from past issues of the Journal, including the common ion effect, the silver tree, crystal formation from supersaturated solutions, making iron passive with nitric acid, optical activity, carbon dioxide in human breath, and amphoteric hydroxides.
Kolb, Doris, editor J. Chem. Educ. 1987, 64, 805.
Aqueous Solution Chemistry |
Chirality / Optical Activity |
Acids / Bases
|
Assigning absolute configuration: Another view Hambly, Gordon F.
Should we be teaching a two-dimensional gimmick when stereochemistry is so vital to organic chemistry?
Hambly, Gordon F. J. Chem. Educ. 1987, 64, 732.
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
|
Assigning absolute configuration Bunting, John W.
Ayorinde's method has a feature that has the potential for creating considerable confusion among students.
Bunting, John W. J. Chem. Educ. 1987, 64, 731.
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
|
Characterizing a tetrahedral intermediate in an acyl transfer reaction: An undergraduate 1H NMR demonstration Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan
A simple experiment involving the detection by 1H NMR spectroscopy of a stable intermediate formed by nucleophilic attack and its characterization as a chiral species.
Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan J. Chem. Educ. 1987, 64, 725.
NMR Spectroscopy |
Nucleophilic Substitution |
Chirality / Optical Activity
|
The spontaneous resolution of cis-bis(ethylenediamine)dinitrocobalt(III) salts: Alfred Werner's overlooked opportunity Bernal, Ivan; Kauffman, George B.
Geometric isomerism and proof of the octahedral configuration; optical isomerism and proof of the octahedral configuration; and the spontaneous resolution of coordination compounds.
Bernal, Ivan; Kauffman, George B. J. Chem. Educ. 1987, 64, 604.
Coordination Compounds |
Women in Chemistry |
Chirality / Optical Activity
|
The nomenclature of relative stereochemistry: Choosing between likes and preferences Brook, Michael A.
The commonly used descriptors for relative stereochemistry are introduced and compared.
Brook, Michael A. J. Chem. Educ. 1987, 64, 218.
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
|
Synthesis and evaluation of the sex pheromone of the bagworm moth Schwarz, Meyer; Klun, J. A.
Several possible student-oriented experiments at different educational levels can look into the interesting chemistry involved in a naturally occurring optically active pheromone.
Schwarz, Meyer; Klun, J. A. J. Chem. Educ. 1986, 63, 1014.
Undergraduate Research |
Natural Products |
Synthesis |
Qualitative Analysis |
Chirality / Optical Activity
|
Simple rule for the conversion of Fischer monosaccharide projection formulas into Haworth representations Argiles, J. M.
Many students struggle with memorizing Haworth structures, the authors provide some insight on this topic to help students.
Argiles, J. M. J. Chem. Educ. 1986, 63, 927.
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity |
Carbohydrates |
Molecular Modeling
|
Stereochemistry and the origins of life Brewster, James H.
Does the monochirality of life indicate supernatural creation? Let us give science a chance, as philosophy and religion have had thousands of years to come up with their answers.
Brewster, James H. J. Chem. Educ. 1986, 63, 667.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
The enzymatic resolution of aromatic amino acids Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D.
This article presents an experiment that can demonstrate as many principles of steroisomersim as possible and is also efficient in terms of time and preparation.
Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D. J. Chem. Educ. 1986, 63, 646.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Aromatic Compounds |
Amino Acids |
Enzymes
|
Total Synthesis of Natural Products: The 'Chiron' Approach (Hanessian, Stephen) Wade, Leroy G., Jr.
Details the use of carbohydrate derivatives as chiral starting points for the synthesis of chiral products.
Wade, Leroy G., Jr. J. Chem. Educ. 1985, 62, A190.
Natural Products |
Synthesis |
Carbohydrates |
Chirality / Optical Activity
|
A critical point Gonzalez, Orestes J.
Some troublesome gaps in the theory of evolution have been overlooked.
Gonzalez, Orestes J. J. Chem. Educ. 1985, 62, 503.
Synthesis |
Chirality / Optical Activity |
Stereochemistry
|
Determination of stereochemical relationships Ayorinde, Folahan O.
A sequence of steps to enable students to arrive with relative ease at correct stereochemical relationships.
Ayorinde, Folahan O. J. Chem. Educ. 1985, 62, 297.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Diastereomers
|
The R/S system: A method for assignment and some recent modifications Eliel, Ernest L.
A method that can be applied to all three-dimensional formulas.
Eliel, Ernest L. J. Chem. Educ. 1985, 62, 223.
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
|
Fingertip assignment of absolute configuration Mattern, Daniell Lewis
Modification of an earlier procedure using the arm and first three fingers to aid in the assignment of R or S absolute configuration to chiral centers.
Mattern, Daniell Lewis J. Chem. Educ. 1985, 62, 191.
Stereochemistry |
Chirality / Optical Activity
|
A proposed new convention for graphic presentation of molecular geometry and topography Maehr, Hubert
A review of the popular conventions for drawing molecular structures and a proposal to define strictly graphic symbols in terms of topographic and geometric descriptor properties.
Maehr, Hubert J. Chem. Educ. 1985, 62, 114.
Molecular Modeling |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity
|
A simple polarimeter and experiments utilizing an overhead projector Dorn, H. C.; Bell, H.; Birkett, T.
Design and application of an overhead polarimeter that relies on small amounts of chiral solution and provides a "dual beam" light source for direct comparison of plane-polarized light emerging from chiral and achiral media.
Dorn, H. C.; Bell, H.; Birkett, T. J. Chem. Educ. 1984, 61, 1106.
Laboratory Equipment / Apparatus |
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
|
Models for illustrating chirality at two centers Feldman, Martin R.
This note suggests common objects that can be used as models to illustrate chirality at two centers, and to introduce the concepts of diastereomers and the meso configuration.
Feldman, Martin R. J. Chem. Educ. 1984, 61, 1050.
Molecular Properties / Structure |
Molecular Modeling |
Chirality / Optical Activity |
Diastereomers |
Stereochemistry |
Enantiomers
|
The possible chirality of tetrahedral carbon atoms with two substituents of identical constitution Schafer, Lothar; Van Alsenoy, C.; Van Den Enden, L.
Because of differences in bond angles, species of the form Cabc2 may in fact be chiral.
Schafer, Lothar; Van Alsenoy, C.; Van Den Enden, L. J. Chem. Educ. 1984, 61, 945.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers
|
Examples of diastereomers Bell, William
Using right- and left-handed doors as examples of familiar objects that exhibit enantiomerism.
Bell, William J. Chem. Educ. 1984, 61, 901.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure |
Chirality / Optical Activity
|
"Absolutely" simple stereochemistry Beauchamp, Philip S.
Using the arm and fingers to determine the stereochemistry of chiral centers.
Beauchamp, Philip S. J. Chem. Educ. 1984, 61, 666.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
|
R/S: Apple stereochemistry program Barone, Rene; Meyer, Roger; Arbelot, Michel
51. Bits and pieces, 20. Computer program for helping students to learn R/S conventions.
Barone, Rene; Meyer, Roger; Arbelot, Michel J. Chem. Educ. 1984, 61, 524.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Enrichment / Review Materials
|
Specification of R/S in a multichiral molecule (3) Aronson, John N.
Any system, simple or complex, cannot be used successfully to relate the R, S designations to Fischer projections if an incorrect two-dimensional projection is made of the three-dimensional model of the structure.
Aronson, John N. J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
|
Specification of R/S in a multichiral molecule (2) Milakofsky, Louis
Suggested method has been presented before.
Milakofsky, Louis J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
|
Specification of R/S in a multichiral molecule (1) Diehl, Justin W.
Suggested method becomes extremely difficult for a multichiral molecule.
Diehl, Justin W. J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
|
The determination of the stereochemistry of erythro-1,2-diphenyl-1,2-ethanediol: an undergraduate organic experiment Rowland, Alex T.
The author describes a successful experiment that has been conducted by first-year organic chemistry students which illustrates the power of H NMR spectroscopy in a configuration determination.
Rowland, Alex T. J. Chem. Educ. 1983, 60, 1084.
Phenols |
Alcohols |
NMR Spectroscopy |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
A new gimmick for assigning absolute configuration Ayorinde, F. O.
One of the most challenging aspects of stereochemistry for students is the assignment of configurational symbol (R or S). To solve this problem, a recommendation is illustrated in this article.
Ayorinde, F. O. J. Chem. Educ. 1983, 60, 928.
Stereochemistry |
Chirality / Optical Activity
|
Cyclohexane stereochemistry Dauphinee, G. A.; Forrest, T. P .
44. Bits and pieces, 16. The authors report on a graphic program for cyclohexane stereochemistry which has proven to be highly successful in developing both visualization aptitude and drawing skills.
Dauphinee, G. A.; Forrest, T. P . J. Chem. Educ. 1983, 60, 732.
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Molecular Modeling
|
Two-dimensional chirality in three-dimensional chemistry Wintner, Claude E.
The author points out a valuable way to enhance students' understanding of 3-dimensional stereochemistry: through the concept of 2-dimensional chirality.
Wintner, Claude E. J. Chem. Educ. 1983, 60, 550.
Stereochemistry |
Chirality / Optical Activity |
Molecular Properties / Structure
|
The flat and direct way to R and S configurations: two-dimensional designation of absolute configuration Brun, Y.; Leblanc, P.
Teaching stereochemistry poses a challenge to teachers when representations are two-dimensional. These authors suggest a method where students convert wedge representations into Fischer projections. This offers some pedagogical advantages.
Brun, Y.; Leblanc, P. J. Chem. Educ. 1983, 60, 403.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
Resolvability and the tetrahedral configuration of carbon Kauffman, George B.
A popular explanation about the tetrahedral configuration of carbon is not entirely accurate.
Kauffman, George B. J. Chem. Educ. 1983, 60, 402.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Enantiomers |
X-ray Crystallography |
Stereochemistry |
Chirality / Optical Activity
|
Absolute configuration in a Fischer projection: a simple approach Bhushan, Ravi; Bhattacharjee, G.
First year undergraduates find it hard to assign absolute configuration to a chiral center when the lowest priority group is either to the left or right of the horizontal line.
Bhushan, Ravi; Bhattacharjee, G. J. Chem. Educ. 1983, 60, 191.
Chirality / Optical Activity |
Molecular Properties / Structure |
Molecular Modeling
|
Determination of chiral molecule configuration in Fischer projections Epling, Gary A.
A non-mathematical procedure that students can use to master and remember the determination of R or S configuration.
Epling, Gary A. J. Chem. Educ. 1982, 59, 650.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
|
Reactions between chiral molecules: A handy analogy Richardson, W. S.
Simulating a reaction between R and S structures through the shaking of hands.
Richardson, W. S. J. Chem. Educ. 1982, 59, 649.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Reactions
|
A simple method for specifying the R/S configuration about a chiral center Idoux, John P.
A method for specifying the R/S configuration about a chiral center that does not require the use of a three-dimensional model or the visualization of such a model or the memorization of an arbitrary number system.
Idoux, John P. J. Chem. Educ. 1982, 59, 553.
Chirality / Optical Activity |
Molecular Properties / Structure
|
Sulcatol: Synthesis of an aggregation pheromone Black, Shirley-Ann; Slessor, Keith N.
Synthesis of the aggregation pheromone of the ambrosia beetle, an insect pest of harvested timber in the Pacific North Coast.
Black, Shirley-Ann; Slessor, Keith N. J. Chem. Educ. 1982, 59, 255.
Synthesis |
Natural Products |
Molecular Properties / Structure |
Chirality / Optical Activity |
NMR Spectroscopy |
IR Spectroscopy |
Applications of Chemistry
|
Invert sugar (and a honey of a problem) Wendland, Ray
Question regarding the optical rotation of sucrose, and a sucrose/dextrose/levulose mixture.
Wendland, Ray J. Chem. Educ. 1982, 59, 217.
Carbohydrates |
Chirality / Optical Activity |
Enzymes
|
The Molecular Basis of Optical Activity (Charney, Eliot) Douglas, Bodie
Douglas, Bodie J. Chem. Educ. 1981, 58, A29.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
|
Some developments in the stereochemistry of coordination compounds in the last fifty years Bailar, John C., Jr.
This article is taken from the author's Perspective Lecture and begins with a description of how the author had to successfully narrow his topic in order to fit it into the allotted time, a testimony to the diversity of a "specialist."
Bailar, John C., Jr. J. Chem. Educ. 1981, 58, 674.
Stereochemistry |
Coordination Compounds |
Enantiomers |
Chirality / Optical Activity
|
Calculation and specification of the multiple chirality displayed by sugar pyranoid ring structures Shallenberger, Robert S.; Wrolstad, Ronald E.; Kerschner, Laurie E.
Calculation and specification of the multiple chirality displayed by sugar pyranoid ring structures.
Shallenberger, Robert S.; Wrolstad, Ronald E.; Kerschner, Laurie E. J. Chem. Educ. 1981, 58, 599.
Chemometrics |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers |
Carbohydrates
|
Stereochemistry and macromolecules: Principles and applications Quirk, Roderic P.
This article was written to provide an introduction to the basic concepts of polymer stereochemistry and their applications.
Quirk, Roderic P. J. Chem. Educ. 1981, 58, 540.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
Lagormorphs and enantiomorphs-simple stereomodels Garrett, James M.; Henry, Bruce A.; Cates, Charles R.
Rabbits can help us understand stereochemistry.
Garrett, James M.; Henry, Bruce A.; Cates, Charles R. J. Chem. Educ. 1981, 58, 448.
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
A helpful stereochemical instructional tool England, Don
The figure found in this note has been helpful in aiding student understanding of stereochemistry.
England, Don J. Chem. Educ. 1981, 58, 31.
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Diastereomers |
Enantiomers
|
Rubber gloves, rubber balls, and optical activity Perkins, Robert
Several demonstrations aimed at helping students to understand optical activity.
Perkins, Robert J. Chem. Educ. 1980, 57, 809.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
|
Facile assignment of R,S designations to Fischer projections Price, Howard C.
Suggests a method of assigning R,S designations to Fischer projections that easier than that described in the cited article.
Price, Howard C. J. Chem. Educ. 1980, 57, 528.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
|
Optical Activity Mickey, Charles D.
Historical background of stereoisomerism, the properties of light, the principles of a polarimeter, and optically active compounds.
Mickey, Charles D. J. Chem. Educ. 1980, 57, 442.
Stereochemistry |
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
|
Rotation of plane-polarized light: A simple model Hill, Roger R.; Whatley, Barrie G.
A simple model that explains why enantiomers of a chiral compound rotate light in different directions.
Hill, Roger R.; Whatley, Barrie G. J. Chem. Educ. 1980, 57, 306.
Photochemistry |
Molecular Modeling |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers |
Molecular Properties / Structure
|
Glutamic acid in pheromone synthesis: A useful chiral synthon Smith, Leverett R.; Williams, Howard J.
Outlines synthetic routes for the formation of various pheromones from glutamic acid.
Smith, Leverett R.; Williams, Howard J. J. Chem. Educ. 1979, 56, 696.
Synthesis |
Chirality / Optical Activity |
Natural Products |
Stereochemistry |
Enantiomers |
Amino Acids
|
Configurational and conformational relations among sugars Martin, R. Bruce
Presents a diagram that illustrates the epimeric and other isomeric relationships that exist among the aldohexoses.
Martin, R. Bruce J. Chem. Educ. 1979, 56, 641.
Carbohydrates |
Molecular Properties / Structure |
Conformational Analysis |
Chirality / Optical Activity |
Enantiomers
|
Prochirality and the English beer glass Sanders, J. K. M.
The English beer glass represents an ideal model for illustrating the concepts of prochirality and assymetric induction.
Sanders, J. K. M. J. Chem. Educ. 1979, 56, 594.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
Determination of chiral molecule configuration using the 1,2,5 Rule Dietzel, Richard Adams
Determining R / S configurations using the 1,2,5 rule.
Dietzel, Richard Adams J. Chem. Educ. 1979, 56, 451.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
The determination of enantiomeric purity using a chiral lanthanide shift reagent: An undergraduate organic experiment McGoran, Ernest C.; Cutter, Bruce; Morse, Karen
A convenient alternative for determining the enantiomeric purity of student resolved alpha-phenylethyl amine using a chiral lanthanide shift reagent.
McGoran, Ernest C.; Cutter, Bruce; Morse, Karen J. Chem. Educ. 1979, 56, 122.
Enantiomers |
Chirality / Optical Activity |
Molecular Properties / Structure
|
CHIRAL-a computer aided application of the Cahn-lngold-Prelog rules Meyer, Edgar F., Jr.
The author describes a computer program that will generate information about isomers.
Meyer, Edgar F., Jr. J. Chem. Educ. 1978, 55, 780.
Diastereomers |
Constitutional Isomers |
Enantiomers |
Chirality / Optical Activity |
Chemometrics
|
Microbial conversion of d-sorbitol to l-sorbose. An interdisciplinary experiment illustrating an industrial process Volker, Eugene J.; Schultz, Clyde
A procedure for an interdisciplinary experiment illustrating an industrial process.
Volker, Eugene J.; Schultz, Clyde J. Chem. Educ. 1978, 55, 673.
Industrial Chemistry |
Chirality / Optical Activity |
Synthesis
|
Use of hand models for assigning configurational nomenclature Garrett, James M.
A subject which often produces consternation in a beginning student in organic chemistry is that of sequential nomenclature involving chiral centers. After having studied the Cahn-Ingold-Prelog rules of nomenclature a student may be asked to examine a structure as shown in this article.
Garrett, James M. J. Chem. Educ. 1978, 55, 493.
Nomenclature / Units / Symbols |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
Molecular models based on Petri dishes Yeadon, A.
The construction and use of several models of Petri dishes that can be used to model stereochemistry are presented in this paper.
Yeadon, A. J. Chem. Educ. 1978, 55, 39.
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Group Theory / Symmetry
|
Chirality, diastereoisomerism, and the Narwhal Stirling, C. J.
There are many simple examples of enantiomeric objects, both natural and man-made and their static interrelationship is directly and tellingly examined with the aid of a mirror.
Stirling, C. J. J. Chem. Educ. 1978, 55, 32.
Enantiomers |
Chirality / Optical Activity
|
Synthesis and properties of an optically active complex: A polarimeter experiment for general chemistry Hunt, Harold R., Jr.
Synthesizing and determining the optical rotation of d-Co(phen)3(ClO4)3.2H2O.
Hunt, Harold R., Jr. J. Chem. Educ. 1977, 54, 710.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Coordination Compounds
|
From the concept of relative configuration to the definition of erythro and threo Gielen, Marcel
Defines the relative configuration of two chiral centers and uses this concept to define erythro and threo.
Gielen, Marcel J. Chem. Educ. 1977, 54, 673.
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
Chirality of the disulfide bond in biomolecules Panijpan, Bhinyo
Draws attention to the chirality of the disulfide bond and its significance in the structure and activity of biomolecules.
Panijpan, Bhinyo J. Chem. Educ. 1977, 54, 670.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers
|
The use of an Eskimo yo-yo to demonstrate circular dichroism and optical rotation Meloan, Clifton E.; Gere, Dennis
Using an Eskimo yo-yo to demonstrate circular dichroism and optical rotation.
Meloan, Clifton E.; Gere, Dennis J. Chem. Educ. 1977, 54, 577.
Chirality / Optical Activity
|
Addendum to "Simple demonstration of optical activity" Dean, Walter K.
Modifications to an earlier demonstration on optical activity.
Dean, Walter K. J. Chem. Educ. 1977, 54, 494.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers
|
A Device for easy demonstration of optical activity and optical rotatory dispersion Kinney, John B.; Skinner, James F.
Describes a portable device that can be used for the simultaneous demonstration of both optical activity and optical rotatory dispersion for individual students and for a class with an overhead projector.
Kinney, John B.; Skinner, James F. J. Chem. Educ. 1977, 54, 494.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Laboratory Equipment / Apparatus
|
A simple demonstration of optical activity Fernandez, Jack E.
Apparatus and instructions for a simple demonstration of optical activity.
Fernandez, Jack E. J. Chem. Educ. 1976, 53, 508.
Chirality / Optical Activity |
Enantiomers
|
Permanent models for determining absolute configurations Thoman, Charles J.
The purpose of this report is to describe briefly how hands may be used to determine R and S configurations.
Thoman, Charles J. J. Chem. Educ. 1976, 53, 502.
Enantiomers |
Chirality / Optical Activity |
Molecular Properties / Structure
|
The resolution of racemic acid: A classic stereochemical experiment for the undergraduate laboratory Kauffman, George B.; Myers, Robin D.
Includes historical background of Pasteur's work and a procedure for investigating the relations between the tartaric acids, racemic acid, and their sodium ammonium salts.
Kauffman, George B.; Myers, Robin D. J. Chem. Educ. 1975, 52, 777.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
|
Determining chirality Mayper, Stuart A.
The referenced method is essentially a restatement of an earlier procedure.
Mayper, Stuart A. J. Chem. Educ. 1975, 52, 686.
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
|
Rediscovery in a course for nonscientists. Use of molecular models to solve classical structural problems Wood, Gordon W.
Describes exercises using simple ball and stick models that students with no chemistry background can solve in the context of the original discovery.
Wood, Gordon W. J. Chem. Educ. 1975, 52, 177.
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Nonmajor Courses
|
Optical rotary dispersion and circular dichroism Wong, Kin-Ping
This paper will discuss briefly the basic concepts of the phenomenon of optical rotary dispersion and will devote the major portion to instrumentation and the experimental aspects of such measurements.
Wong, Kin-Ping J. Chem. Educ. 1974, 51, A573.
Chirality / Optical Activity |
Laboratory Equipment / Apparatus
|
The sequence rules Fernelius, W. C.; Loening, Kurt; Adams, Roy M.
The authors explain the usefulness of the sequence rules in learning about chirality.
Fernelius, W. C.; Loening, Kurt; Adams, Roy M. J. Chem. Educ. 1974, 51, 735.
Nomenclature / Units / Symbols |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers |
Coordination Compounds
|
The odor of optical isomers-An amendment Mitchell, R. H.; West, P. R.
The authors report a modification of Morov and Pickering's excellent example in which they use column chromatography on Silica Gel to separate the components of the oils.
Mitchell, R. H.; West, P. R. J. Chem. Educ. 1974, 51, 274.
Chirality / Optical Activity |
Diastereomers |
Chromatography |
Physical Properties
|
A simple dynamic stereomodel for the interconversion of enantiomers via a high-energy achiral intermediate Stirling, C. J. M.
A simple dynamic stereomodel for the interconversion of enantiomers via a high-energy achiral intermediate because introduction of molecular chirality to the elementary students is often effectively made by the comparison of familiar chiral and achiral objects.
Stirling, C. J. M. J. Chem. Educ. 1974, 51, 50.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Modeling
|
Some stereochemical principles from polymers. Molecular symmetry and molecular flexibility Price, Charles C.
The properties of polymers from ethylene, propylene, isobutylene, and the three related epoxides, can be used to illustrate several important basic principles relating chemical structure to properties.
Price, Charles C. J. Chem. Educ. 1973, 50, 744.
Conferences |
Professional Development |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
A simple demonstration of enantiomerism Richards, K. E.
Design for a wooden box containing a mirror that uses a molecular model to demonstrate enantiomerism.
Richards, K. E. J. Chem. Educ. 1973, 50, 632.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
An overhead projection demonstration of optical activity Hill, John W.
An overhead projection demonstration of optical activity the makes use of two polarizing lenses and an optically active compound.
Hill, John W. J. Chem. Educ. 1973, 50, 574.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Carbohydrates
|
Spontaneous generation of optical activity Pincock, Richard E.; Wilson, Keith R.
Reviews the background that has led to the attitude that spontaneous generation of optical activity is not possible, and identifies those published examples of this phenomenon.
Pincock, Richard E.; Wilson, Keith R. J. Chem. Educ. 1973, 50, 455.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry
|
Sterospecificity in the palm of your hand Treptow, Richard S.
A simple demonstration to illustrate the reaction between two optically active agents.
Treptow, Richard S. J. Chem. Educ. 1973, 50, 131.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
|
The odor of optical isomers. An experiment in organic chemistry Murov, Steven L.; Pickering, Miles
The experiment described involves the separation and characterization of l-carvone from spearmint oil and d-carvone from caraway seed oil.
Murov, Steven L.; Pickering, Miles J. Chem. Educ. 1973, 50, 74.
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Separation Science
|
Complementary rules to define R or S configuration. Viewing molecules from any side Cori, O.
Reviews the rules to specify the configuration of a chiral center.
Cori, O. J. Chem. Educ. 1972, 49, 461.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Properties / Structure
|
The concept of dissymmetric worlds. A utilization of the power of optical isomerism Abernethy, John L.
Elaborates on the concept of dissymmetric worlds and the dependence of life on dissymmetric compounds.
Abernethy, John L. J. Chem. Educ. 1972, 49, 455.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
|
The natural origin of optically active compounds Elias, W. E.
There are plausible explanations, based on natural processes, by which organic compounds mat have been produced and then converted into structures of unique chirality.
Elias, W. E. J. Chem. Educ. 1972, 49, 448.
Natural Products |
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
|
A model for demonstrating helical dissymmetry Magliulo, Anthony R.
Ordinary pipe cleaners can be used to illustrate the concept of helical dissymmetry.
Magliulo, Anthony R. J. Chem. Educ. 1972, 49, 391.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
Chirality in Sea Shells Plumb, Robert C.; Martin, Dean F.
Gastropods exhibit a preference for either right- or left-handed spirals.
Plumb, Robert C.; Martin, Dean F. J. Chem. Educ. 1972, 49, 330.
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
|
A model for demonstrating the rotation of polarized light by an asymmetric molecule Berry, James P.
A nut and bolt (representing an asymmetric molecule and a beam of plane-polarized light) are used to illustrate that regardless of which face of the nut is up, one must rotate the bolt counterclockwise to cause it to pass downward through the nut.
Berry, James P. J. Chem. Educ. 1970, 47, 659.
Molecular Properties / Structure |
Molecular Mechanics / Dynamics |
Chirality / Optical Activity |
Enantiomers
|
LTE. Rule of thumb for predicting optical activity Mowery, Dwight F., Jr.
The author clarifies a point made in his earlier article.
Mowery, Dwight F., Jr. J. Chem. Educ. 1969, 46, 700.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
|
The resolution of DL-histidine: An organic chemistry experiment using an ion exchange resin Bosch, Arthur J.
This experiment involves the isolation of the amino acid, D-histidine, from DL-histidine, and gives a product with high optical purity while demonstrating the use of an ion exchange resin and mixed solvent recrystallization.
Bosch, Arthur J. J. Chem. Educ. 1969, 46, 691.
Ion Exchange |
Amino Acids |
Chirality / Optical Activity |
Enantiomers
|
Construction and uses of an inexpensive polarimeter Vennos, Mary S.
Presents a design of an inexpensive polarimeter and its use to determine the specific rotation of sucrose and the concentration of an unknown sucrose solution.
Vennos, Mary S. J. Chem. Educ. 1969, 46, 459.
Laboratory Equipment / Apparatus |
Photochemistry |
Chirality / Optical Activity |
Enantiomers |
Instrumental Methods |
Noncovalent Interactions
|
An NMR determination of optical purity: An advanced undergraduate laboratory experiment Jacobus, John; Raban, Morton
Presents an advanced organic laboratory applying NMR spectroscopy to the determination of optical purity that illustrates several important stereochemical concepts.
Jacobus, John; Raban, Morton J. Chem. Educ. 1969, 46, 351.
NMR Spectroscopy |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Diastereomers |
Molecular Properties / Structure
|
Criteria for optical activity in organic molecules Mowery, Dwight F., Jr.
Develops criteria for predicting the possible existence of optical activity in organic molecules.
Mowery, Dwight F., Jr. J. Chem. Educ. 1969, 46, 269.
Chirality / Optical Activity |
Molecular Properties / Structure
|
A simplified proof of the constitution and configuration of D-glucose Frohwein, Y, Z.
Presents a simplified proof of the constitution and configuration of D-glucose for students being introduced to carbohydrate chemistry.
Frohwein, Y, Z. J. Chem. Educ. 1969, 46, 55.
Carbohydrates |
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
|
Optical rotary dispersion in transparent media Henderson, Giles Lee
It is the purpose of this paper to describe a more complete analysis of optical activity in the visible spectrum; includes a procedure using D-camphor to illustrate rotatory dispersion.
Henderson, Giles Lee J. Chem. Educ. 1968, 45, 515.
Chirality / Optical Activity
|
Molecular symmetry and optical inactivity Carlos, Jose L., Jr.
Presents a criterion for optical inactivity that is both sufficient and easily applicable.
Carlos, Jose L., Jr. J. Chem. Educ. 1968, 45, 248.
Molecular Properties / Structure |
Chirality / Optical Activity
|
A TV lecture demonstration of optical activity Henderson, Giles L.
This demonstration relies on a television camera and polarimeter optics.
Henderson, Giles L. J. Chem. Educ. 1967, 44, 765.
Chirality / Optical Activity
|
Resolution of D,L-alpha-phenylethylamine: An introductory organic chemistry experiment Ault, Addison
This experiment clarifies several of the concepts of optical isomerism and introduces the techniques of recrystallization, extraction, and distillation.
Ault, Addison J. Chem. Educ. 1965, 42, 269.
Amines / Ammonium Compounds |
Enantiomers |
Chirality / Optical Activity
|
Optical rotation Evans, J. O. M.; Tietze, H. R.
The angle of rotation of sucrose can be easily determined using this simple demonstration.
Evans, J. O. M.; Tietze, H. R. J. Chem. Educ. 1964, 41, A973.
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
|
Systematic names for the tartaric acids Baxter, J. N.
Examines the use of the small capital letters D and L in naming tartaric acids.
Baxter, J. N. J. Chem. Educ. 1964, 41, 619.
Nomenclature / Units / Symbols |
Acids / Bases |
Carbohydrates |
Chirality / Optical Activity |
Enantiomers
|
The rotation of optically pure 2-bromooctane Traynham, James C.
This paper reviews the various values reported for the optical rotation of pure 2-bromooctane and makes a case for its most probable value.
Traynham, James C. J. Chem. Educ. 1964, 41, 617.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
|
Resolving coordination compounds by a second order asymmetric synthesis Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K.
This experiment involves the resolution of an optically active complex cation, the trisoxalatochromate(III) ion and provides the student with an excellent introduction to the phenomenon of second order asymmetric synthesis.
Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K. J. Chem. Educ. 1964, 41, 461.
Diastereomers |
Coordination Compounds |
Chirality / Optical Activity
|
An introduction to the sequence rule: A system for the specification of absolute configuration Cahn, R. S.
This paper describes the relatively simple methods that suffice for specifying the absolute configuration of the majority of optically active organic compounds - those containing asymmetric carbon atoms.
Cahn, R. S. J. Chem. Educ. 1964, 41, 116.
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Nomenclature / Units / Symbols
|
The stereochemistry of complex inorganic compounds Busch, Daryle H.
Examines optical activity, absolute configuration, stereospecificity, linkage isomers, electronic isomers, and template reactions.
Busch, Daryle H. J. Chem. Educ. 1964, 41, 77.
Stereochemistry |
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Chirality / Optical Activity |
Stereochemistry |
Molecular Properties / Structure
|
Three-dimensional effects in biochemistry Ingraham, Lloyd L.
Explores stereospecificity and stereoselectivity; rigidity requirements; steric effects; and stereospecificity when not required mechanistically.
Ingraham, Lloyd L. J. Chem. Educ. 1964, 41, 66.
Molecular Properties / Structure |
Catalysis |
Enzymes |
Molecular Recognition |
Mechanisms of Reactions |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
Letters Koons, Lawrence F.
Calls attention to a demonstration similar to that described in an earlier article.
Koons, Lawrence F. J. Chem. Educ. 1962, 39, 318.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
|
Resolving optically-active coordination compounds: An experiment for the inorganic laboratory Kauffman, George B.; Takahashi, Lloyd T.
Resolution of the tris (1,10-phenanthroline)nickel(II) ion or the trisoxalatocobaltate(III) ion into their optical antipodes.
Kauffman, George B.; Takahashi, Lloyd T. J. Chem. Educ. 1962, 39, 481.
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers
|
The configuration of (-)-shikimic acid and certain biochemically related compounds Hanson, Kenneth R.
Points out errors in representations of the structures of important biological derivatives of 5-dehydroquinic acid II.
Hanson, Kenneth R. J. Chem. Educ. 1962, 39, 419.
Aromatic Compounds |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Plant Chemistry
|
A model for optical rotation Jones, L. L.; Eyring, Henry
Examines the history of work on optical activity and a harmonic oscillator model for this phenomenon.
Jones, L. L.; Eyring, Henry J. Chem. Educ. 1961, 38, 601.
Chirality / Optical Activity
|
The criterion for optical isomerism Thompson, H. Bradford
The absence of planes or centers of symmetry is not a criterion for optical isomerism.
Thompson, H. Bradford J. Chem. Educ. 1960, 37, 530.
Chirality / Optical Activity |
Enantiomers |
Molecular Properties / Structure
|
Ciphered formulas in carbohydrate chemistry Difini, Alvaro; Neto, Jose Difini
Describes the use of schematic formulas as an aid to rapidly representing configurations for monosaccharides.
Difini, Alvaro; Neto, Jose Difini J. Chem. Educ. 1958, 35, 38.
Carbohydrates |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Chirality / Optical Activity
|
Letters to the editor Mayper, Stuart A.
The author analyzes more closely a dismissed method for representing hexacovalent complexes with specific configurations.
Mayper, Stuart A. J. Chem. Educ. 1957, 34, 623.
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
The chemical problem of spontaneous generation Fox, Sidney W.
Examines research regarding the origin of life.
Fox, Sidney W. J. Chem. Educ. 1957, 34, 472.
Atmospheric Chemistry |
Amino Acids |
Chirality / Optical Activity
|
Letters to the editor Freedman, Jules
Commentary on the D and L convention as applied to tartaric acid.
Freedman, Jules J. Chem. Educ. 1957, 34, 362.
Acids / Bases |
Stereochemistry |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Enrichment / Review Materials |
Chirality / Optical Activity
|
Letters to the editor Pickering, Roger A.
Commentary on the D and L convention as applied to tartaric acid.
Pickering, Roger A. J. Chem. Educ. 1957, 34, 362.
Stereochemistry |
Nomenclature / Units / Symbols |
Acids / Bases |
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
|
Assignment of D and L prefixes to the tartaric acids Vickery, Hubert Bradford
Discusses conventions regarding the assignment of D and L prefixes to the tartaric acids.
Vickery, Hubert Bradford J. Chem. Educ. 1957, 34, 339.
Molecular Properties / Structure |
Enantiomers |
Stereochemistry |
Chirality / Optical Activity |
Nomenclature / Units / Symbols
|
A chart of the stereochemical relationships of the aldoses Nelson, Peter F.
Provides a chart of the stereochemical relationships of the aldoses that allows students to review and visualize the Rosanoff classification by comparing the D and L enantiomeric forms.
Nelson, Peter F. J. Chem. Educ. 1957, 34, 179.
Stereochemistry |
Molecular Properties / Structure |
Carbohydrates |
Enantiomers |
Chirality / Optical Activity
|
Assignment of D and L prefixes to the tartaric acids: The Wohl conventions Abernethy, John Leo
Examines the Wohl system for designating dextro- and levorotatory tartaric acids.
Abernethy, John Leo J. Chem. Educ. 1957, 34, 150.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry |
Chirality / Optical Activity |
Acids / Bases
|
Assignment of D and L prefixes to the tartaric acids: An unsettled stereochemical question Nenitzescu, Costin D.
Examines the Wohl and Freudenberg systems of designating dextro- and levorotatory tartaric acids.
Nenitzescu, Costin D. J. Chem. Educ. 1957, 34, 147.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Acids / Bases |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
Letters to the editor Gorin, George
Amplifies the discussion of proper configurational prefixes for the tartaric acids.
Gorin, George J. Chem. Educ. 1956, 33, 478.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
|
Some difficulties and common errors related to the designation of sugar configurations Abernethy, John Leo
Examines some difficulties and common errors related to the designation of sugar configurations.
Abernethy, John Leo J. Chem. Educ. 1956, 33, 88.
Carbohydrates |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
|
A notation for the study of certain stereochemical problems Newman, Melvin S.
Newman introduces the projections of compounds containing two adjacent asymmetric carbons that would later bear his name.
Newman, Melvin S. J. Chem. Educ. 1955, 32, 344.
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure |
Conformational Analysis |
Chirality / Optical Activity
|
A mailing-tube polarimeter Shaw, William H. R.
This simple but effective polarimeter is constructed from a cardboard tube and a small square of polarizing film.
Shaw, William H. R. J. Chem. Educ. 1955, 32, 10.
Chirality / Optical Activity |
Molecular Properties / Structure
|
The Liebig-Pasteur controversy Finegold, Harold
Recounts the famous Liebig-Pasteur controversy regarding the nature of alcoholic fermentation.
Finegold, Harold J. Chem. Educ. 1954, 31, 403.
Chirality / Optical Activity |
Enzymes
|
Miscellaneous experiments Damerel, Charlotte I.
Offers three demonstrations, the first involving molecular models illustrating the generation of optical isomers in a laboratory synthesis; the second demonstrating that liquid sodium chloride conducts and electric current; and the third examining the flow of electric current in an electrochemical galvanic cell.
Damerel, Charlotte I. J. Chem. Educ. 1952, 29, 296.
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Conductivity |
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials
|
The cause of optical inactivity Mowery, Dwight Fay, Jr.
The cause of optical inactivity is often portrayed erroneously in textbooks.
Mowery, Dwight Fay, Jr. J. Chem. Educ. 1952, 29, 138.
Chirality / Optical Activity |
Molecular Properties / Structure
|
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