TIGER

Journal Articles: 137 results
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 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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
"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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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 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