TIGER

Journal Articles: 174 results
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
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
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 centurya 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 ahydroxyketones 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
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 ahelices to ?sheets.
King, Angela G. J. Chem. Educ. 2006, 83, 10.
Catalysis |
Chirality / Optical Activity |
Proteins / Peptides |
Molecular Modeling |
Molecular Properties / Structure
Cotton Effect in Copper–Proline Complexes in the Visible Region  Victor Volkov and Rolf Pfister
This article suggests taking advantage of the visible dd 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
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
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
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
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
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
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
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
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
"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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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