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Journal Articles: 89 results
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
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
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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
Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-Bromostyrene  Thomas A. Evans
The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.
Evans, Thomas A. J. Chem. Educ. 2006, 83, 1062.
Alkenes |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
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
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
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
A Literature Exercise Using SciFinder Scholar for the Sophomore-Level Organic Chemistry Course  Ian J. Rosenstein
This report details an exercise for the sophomore-level organic course using SciFinder Scholar to search the Chemical Abstracts database. Students each research the synthesis and use of a chiral auxiliary then present their findings to their classmates in a short oral presentation.
Rosenstein, Ian J. J. Chem. Educ. 2005, 82, 652.
Stereochemistry |
Molecular Properties / Structure
A Set of Hands-On Exercises on Conformational Analysis  Silvina C. Pellegrinet and Ernesto G. Mata
This article describes a set of comprehensive exercises on conformational analysis that employs a hands-on approach by the use of molecular modeling kits. In addition, the exercises provide illustrations of other topics such as nomenclature, functional groups, and isomerism, and introduce some notions of chirality.
Pellegrinet, Silvina C.; Mata, Ernesto G. J. Chem. Educ. 2005, 82, 73.
Alkanes / Cycloalkanes |
Conformational Analysis |
Constitutional Isomers |
Molecular Properties / Structure |
Stereochemistry
Demonstration of Enantiomer Specificity of Proteins and Drugs  Gretchen L. Anderson
In addition to the traditional use of molecular models of tetrahedral asymmetric centers, the concept of chirality and its importance to proteindrug interactions is demonstrated in a guided classroom activity.
Anderson, Gretchen L. J. Chem. Educ. 2004, 81, 971.
Enantiomers |
Proteins / Peptides |
Drugs / Pharmaceuticals |
Enzymes |
Chirality / Optical Activity
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
Bromination and Debromination of Cholesterol: An Inquiry-Based Lab Involving Structure Elucidation, Reaction Mechanism, and 1H NMR  Andrew Grant and Devin Latimer
An experiment designed to examine a reaction mechanism and its stereochemical consequences; students propose the product and a mechanism for its production before conducting the experiment and analyzing the product with 1H NMR.
Grant, Andrew S.; Latimer, Devin. J. Chem. Educ. 2003, 80, 670.
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Natural Products |
Synthesis |
Steroids
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
"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
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
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
A Simple Method of Drawing Stereoisomers from Complicated Symmetrical Structures  A. Haudrechy
A practical and systematic method to establish the number and relationships of stereoisomers in cases of complex molecular symmetry is described.
Haudrechy, Arnaud. J. Chem. Educ. 2000, 77, 864.
Stereochemistry |
Molecular Properties / Structure
A New Method To Convert the Fischer Projection of Monosaccharide to the Haworth Projection  Qing-zhi Zhang and Shen-song Zhang
The D,L-configuration of a sugar in Haworth projection can be directly determined by designating the R,S-configuration of the highest-numbered asymmetric carbon; that is, the most distant carbon from the anomeric carbon. The R-configuration at this carbon corresponds to the D-family, and S- to the L-family.
Zhang, Qing-zhi; Zhang, Shen-song. J. Chem. Educ. 1999, 76, 799.
Carbohydrates |
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling
Models and Molecules - A Workshop on Stereoisomers  Robert W. Baker, Adrian V. George, and Margaret M. Harding
A molecular model workshop aimed at first year university undergraduates has been devised to illustrate the concepts of organic stereochemistry. The students build models to teach the relationship within, and between, conformational isomers, enantiomers, and diastereomers.
Baker, Robert W.; George, Adrian V.; Harding, Margaret M. J. Chem. Educ. 1998, 75, 853.
Molecular Properties / Structure |
Stereochemistry |
Molecular Modeling |
Enantiomers |
Diastereomers
Molecules, Crystals, and Chirality  Il-Hwan Suh, Koon Ha Park, William P. Jensen, David E. Lewis*
The development of the concept of chirality from the early work of Pasteur, van't Hoff and Le Bel to the work of Cahn, Ingold and Prelog is presented, and the constraints that chirality imposes on the symmetry of molecules - that chiral molecules may not possess an improper axis of rotation - is discussed.
Suh, Il-Hwan; Park, Koon Ha ; Jensen, William P.; Lewis, David E. J. Chem. Educ. 1997, 74, 800.
Crystals / Crystallography |
Molecular Properties / Structure |
Stereochemistry |
X-ray Crystallography
Chemical Topology: The Ins and Outs of Molecular Structure  Dennis K. Mitchell and Jean-Claude Chambron
Using models of macromolecules to develop and broaden an understanding of bonding and structure; includes many examples of molecules of topological interest.
Mitchell, Dennis K.; Chambron, Jean-Claude. J. Chem. Educ. 1995, 72, 1059.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Molecular Mechanics / Dynamics |
Covalent Bonding
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
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
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
The enumeration of isomers-With special reference to the stereoisomers of decane  Whyte, J. R. C.; Clugston, M. J.
Structural isomers predicted through algorithms.
Whyte, J. R. C.; Clugston, M. J. J. Chem. Educ. 1993, 70, 874.
Alkanes / Cycloalkanes |
Stereochemistry |
Diastereomers
Stereochemistry and the "ether" in the evolution of molecular structure theory: The musings of a chemist on Moller's supplanted "screw-theory", beginning with a view of the obnoxious and equally outdated cod-liver oil  Greenberg, Arthur
A look at a chemist's attempt to explain optical rotation of plane-polarized light by enantiomers documented in a text published in 1895 that the author of this article had stumbled upon.
Greenberg, Arthur J. Chem. Educ. 1993, 70, 284.
Stereochemistry |
Enrichment / Review Materials
Meso and dl diastereomers: Synthesis and 1H NMR study of the 1,3-diphenylpropane-1,3-diols: An advanced undergraduate project in physical organic chemistry  Depres, Jean-Pierre; Morat, Claude
An integrated laboratory project that gives students an experimental approach to diastereomerism in molecular structure and to first- and second-order NMR spectroscopic analysis.
Depres, Jean-Pierre; Morat, Claude J. Chem. Educ. 1992, 69, A232.
Synthesis |
NMR Spectroscopy |
Diastereomers |
Stereochemistry |
Group Theory / Symmetry |
Molecular Properties / Structure
Isomerism in adamantane-like inorganic compounds  Vittal, Jagadese J.
Analysis of the structure and isomerism of adamantane-like inorganic compounds.
Vittal, Jagadese J. J. Chem. Educ. 1992, 69, 955.
Stereochemistry |
Group Theory / Symmetry |
Molecular Properties / Structure
A source of isomer-drawing assignments  Kjonaas, Richard A.
A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.
Kjonaas, Richard A. J. Chem. Educ. 1992, 69, 452.
Stereochemistry |
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Aldehydes / Ketones |
Ethers |
Esters |
Alkynes
Toward the consistent use of regiochemical and stereochemical terms in introductory organic chemistry.  Adams, David L.
Proposes consistency and clarity in the use of definitions for regioselective, stereoselective, and stereospecific in introductory organic chemistry.
Adams, David L. J. Chem. Educ. 1992, 69, 451.
Stereochemistry |
Nomenclature / Units / Symbols
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
An easily constructed model of the chair form of a six-membered ring composed of six distorted tetrahedra penetrating each other.  Yamana, Shukichi.
A model of the chair form of a six-membered ring composed of six distorted tetrahedra penetrating each other is useful for teaching stereorchemistry of organic compounds.
Yamana, Shukichi. J. Chem. Educ. 1992, 69, 216.
Molecular Modeling |
Stereochemistry
Microscale resolution of racemic 1-phenylethylamine and chiral high performance liquid chromatography (HPLC) in undergraduate chemistry   Krumpolc, Miroslav
A standard experiment has been modified to incorporate microscale techniques and employ chiral high performance liquid chromatography to determine enantiomeric purity.
Krumpolc, Miroslav J. Chem. Educ. 1991, 68, A176.
Enantiomers |
Amides |
Diastereomers |
Physical Properties |
Microscale Lab
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
The use of the Desktop Molecular Modeller software in the teaching of structural chemistry  Aduldecha, S.; Akhter, P.; Field, P.; Nagle, P.; O'Sullivan, E.; O'Connor, K.; Hathaway, B. J.
127. A review of a molecular modeling program that can be used for the computer graphic display of molecules, their construction from smaller molecules or fragments, and for the manipulation of molecular structure.
Aduldecha, S.; Akhter, P.; Field, P.; Nagle, P.; O'Sullivan, E.; O'Connor, K.; Hathaway, B. J. J. Chem. Educ. 1991, 68, 576.
Molecular Modeling |
Molecular Properties / Structure |
Crystals / Crystallography |
Stereochemistry
Biocatalysis in organic solvents  Natarajan, K. R.
This article highlights why it is sometimes desirable to select organic solvents when carrying out enzymatic reactions, criteria for solvent selection, effects of organic solvents on enzymes, applications, and future prospects.
Natarajan, K. R. J. Chem. Educ. 1991, 68, 13.
Bioorganic Chemistry |
Synthesis |
Solutions / Solvents |
Catalysis |
Enantiomers |
Enzymes
Magnetic nonequivalence in 1,2-disubstituted ethanes: An organic experiment in NMR spectroscopy  Colborn, Robert E.
The main purpose of this experiment is to help students consider the various couplings available in organic molecules and determine whether specific groups will have identical chemical shifts or not.
Colborn, Robert E. J. Chem. Educ. 1990, 67, 438.
NMR Spectroscopy |
Stereochemistry
Molecular mechanics as an organic chemistry laboratory exercise  Jarret, Ronald M.; Sin, Ny
Molecular mechanics calculations can be used in conjunction with hand-held models for a more complete approach to the instruction of stereochemistry.
Jarret, Ronald M.; Sin, Ny J. Chem. Educ. 1990, 67, 153.
Stereochemistry |
Molecular Modeling |
Molecular Mechanics / Dynamics
Flow chart determination of isomeric relationships  Black, Kersey A.
This flow chart presentation is particularly effective in helping the student to distinguish between the different types of stereochemical relationships.
Black, Kersey A. J. Chem. Educ. 1990, 67, 141.
Stereochemistry
A derivation of the Masamune rule of multiplicativity in double asymmetric induction  Nakayama, Kensaku
The ability to prepare one diastereomeric or enantiomeric isomer in excess in a given chemical transformation where a stereoisomeric distribution of products is possible is currently one of the most highly sought goals in the field of synthetic organic chemistry.
Nakayama, Kensaku J. Chem. Educ. 1990, 67, 20.
Synthesis |
Diastereomers |
Enantiomers
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
Rotation of polarized light by stereoisomers of limonene   Solomon, Sally
Neat samples of limonene stereoisomers are used to demonstrate the rotation of polarized light on an overhead projector.
Solomon, Sally J. Chem. Educ. 1989, 66, 436.
Stereochemistry
Overlooked opportunities in stereochemistry: Part II. The neglected connection between metal-ammines (Alfred Werner) and organic onium compounds (William Jackson Pope)  Kauffman, George B.; Bernal, Ivan
The authors have shown how the work of each of two great stereochemists could have mutually enriched, reinforced, and accelerated the contributions of the other.
Kauffman, George B.; Bernal, Ivan J. Chem. Educ. 1989, 66, 293.
Coordination Compounds |
Stereochemistry
C167H336 is the smallest alkane with more realizable isomers than the observed universe has "particles"  Davies, Robert E.; Freyd, Peter J.
The number of stereoisomers of C167H336 that can exist, though not all at the same time, is greater than the classical figure for the number of particles in the observed universe.
Davies, Robert E.; Freyd, Peter J. J. Chem. Educ. 1989, 66, 278.
Alkanes / Cycloalkanes |
Stereochemistry
Carbohydrate stereochemistry  Shallenberger, Robert S.; Wienen, Wanda J.
A progress in the development of general stereochemical principles has been significantly influenced by studies that led to determination of the crystalline and solution structures of sugars, the subject of carbohydrate chemistry is developed here in historical fashion.
Shallenberger, Robert S.; Wienen, Wanda J. J. Chem. Educ. 1989, 66, 67.
Carbohydrates |
Stereochemistry
Van't Hoff, Le Bel, and the development of stereochemistry: A reassessment  Grossman, Robert B.
The author gives a review of and possible explanations for Van't Hoff's inconsistencies.
Grossman, Robert B. J. Chem. Educ. 1989, 66, 30.
Stereochemistry |
Group Theory / Symmetry
Stereoisomerism in coordination chemistry: A laboratory experiment for undergraduate students  Gargallo, Maria Fe; Lechuga, Laura; Puerta, M. Carmen; Gonzalez-Vilchez, Francisco; Vilaplana, Rosario
This experiment makes students become acquainted with stereochemical concepts and several techniques used in this field and incorporate in the learning some of the recent research tasks.
Gargallo, Maria Fe; Lechuga, Laura; Puerta, M. Carmen; Gonzalez-Vilchez, Francisco; Vilaplana, Rosario J. Chem. Educ. 1988, 65, 1018.
Stereochemistry |
Diastereomers |
Coordination Compounds
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
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
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
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
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
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all  Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
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
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
Diastereomers, geometric isomers, and rotation about bonds  McCullough, John J.
A simple and consistent introduction to the stereochemistry of carbon, diastereomers, and geometric isomers.
McCullough, John J. J. Chem. Educ. 1982, 59, 37.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure
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
Determination of the absolute stereochemistry of secondary alcohols: An advanced organic chemistry experiment for undergraduate students  Bandaranayake, Wickramasinghe M.
Introduces students to the Ingold, Prelog, and Cahn R and S sequence rules.
Bandaranayake, Wickramasinghe M. J. Chem. Educ. 1980, 57, 828.
Alcohols |
Molecular Properties / Structure |
Stereochemistry
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
Stereochemical nonequivalence of ligands and faces (heterotopicity)  Eliel, Ernest L.
Reviews the concepts associated with stereochemical non-equivalence (heterotopicity).
Eliel, Ernest L. J. Chem. Educ. 1980, 57, 52.
Stereochemistry |
Enantiomers |
Diastereomers |
Constitutional Isomers |
Group Theory / Symmetry
Computation of the number of isomers of coordination compounds containing different monodentate ligands  Chung, Chung-Sun

Chung, Chung-Sun J. Chem. Educ. 1979, 56, 398.
Chemometrics |
Molecular Properties / Structure |
Coordination Compounds |
Stereochemistry |
Diastereomers
Permanent models for determining absolute configurations   Thoman, Charles J.
The purpose of this report is to describe briefly how hands may be used to determine R and S configurations.
Thoman, Charles J. J. Chem. Educ. 1976, 53, 502.
Enantiomers |
Chirality / Optical Activity |
Molecular Properties / Structure
The significance of a methyl group in the stereoselectivity of cobalt(lII) complexes  Brubaker, George R.
This paper represents the first attempt to apply methods of conformational analysis to problems of stereochemistry in metal complexes.
Brubaker, George R. J. Chem. Educ. 1974, 51, 608.
Coordination Compounds |
Molecular Mechanics / Dynamics |
Organometallics |
Stereochemistry |
Metals
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
Determination of the relative and absolute configurations of (-)menthol and (+)neomenthol. An introductory stereochemistry experiment  Barry, J.
This activity serves to familiarize students with stereochemistry and the conformational analysis of cyclohexane systems.
Barry, J. J. Chem. Educ. 1973, 50, 292.
Stereochemistry |
Molecular Properties / Structure |
Alcohols |
Conformational Analysis
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
The two faces of D and L nomenclature  Slocum, D. W.; Surgarman, D.; Tucker, S. P.
This paper reviews the conflicts and ambiguities in two older nomenclature methods.
Slocum, D. W.; Surgarman, D.; Tucker, S. P. J. Chem. Educ. 1971, 48, 597.
Stereochemistry |
Nomenclature / Units / Symbols
Recent advances in stereochemical nomenclature  Eliel, Ernest L.
It is the purpose of this brief article to deal with the most significant of the recent nomenclature changes and additions.
Eliel, Ernest L. J. Chem. Educ. 1971, 48, 163.
Nomenclature / Units / Symbols |
Stereochemistry
Resolution and stereochemistry of asymmetric silicon, germanium, tin, and lead compounds  Belloli, Robert
It is the purpose of this review to summarize the results of stereochemical studies on compounds containing an asymmetric group IVA atom.
Belloli, Robert J. Chem. Educ. 1969, 46, 640.
Stereochemistry |
Organometallics |
Enantiomers |
Mechanisms of Reactions |
Nucleophilic Substitution
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
Conformational analysis and chemical reactivity  Idoux, John P.
Uses acyclic chemistry to illustrate important concepts regarding conformational analysis and chemical reactivity.
Idoux, John P. J. Chem. Educ. 1967, 44, 495.
Conformational Analysis |
Stereochemistry |
Diastereomers
Introduction to stereochemistry (Mislow, Kurt)  Petersen, Quentin R.

Petersen, Quentin R. J. Chem. Educ. 1966, 43, A272.
Stereochemistry
On the spatial arrangement of atoms in nitrogen-containing molecules  Hantzsch, A.; Werner, A.
Reprint of Alfred Werner's inaugural dissertation on the one hundredth anniversary of his winning of the first Nobel Prize in chemistry.
Hantzsch, A.; Werner, A. J. Chem. Educ. 1966, 43, 156.
Stereochemistry
Stereochemistry: The static principles (Grundy, J.)  Petersen, Quentin R.

Petersen, Quentin R. J. Chem. Educ. 1965, 42, A494.
Stereochemistry |
Molecular Properties / Structure
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
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
Teaching organic stereochemistry  Eliel, Ernest L.
Focusses on suggestions for the teaching of stereochemistry in general chemistry.
Eliel, Ernest L. J. Chem. Educ. 1964, 41, 73.
Molecular Properties / Structure |
Stereochemistry
Stereochemistry in the terminal course  Evans, Gordon G.
Discusses the role of stereochemistry in the terminal course of students who are not majoring in chemistry.
Evans, Gordon G. J. Chem. Educ. 1963, 40, 438.
Stereochemistry |
Nonmajor Courses
Stereoisomerism of carbon compounds  Noyce, William K.
The purpose of this article is to suggest a different setting for the classification of the various types of stereoisomerism commonly encountered in organic chemistry, with the view to providing a better correlation with contemporary concepts of atomic and molecular structure.
Noyce, William K. J. Chem. Educ. 1961, 38, 23.
Stereochemistry |
Molecular Properties / Structure
Simplified models of inorganic stereoisomers  Kauffman, George B.
The purpose of the proposed models is to demonstrate stereoisomerism as simply as possible.
Kauffman, George B. J. Chem. Educ. 1959, 36, 82.
Molecular Properties / Structure |
Molecular Modeling |
Stereochemistry |
Coordination Compounds
The numbers and structures of isomers of hexacovalent complexes  Bailar, John C., Jr.
The purpose of this article is to outline a simple method of counting the stereoisomers that can be theoretically formed by monodentate or polydentate ligands and of showing their structures.
Bailar, John C., Jr. J. Chem. Educ. 1957, 34, 334.
Coordination Compounds |
Stereochemistry |
Molecular Properties / Structure
Aspects of isomerism and mesomerism. III. Stereoisomerism  Bent, Richard L.
Examines the tetrahedral nature of carbon, multiple bonds, enantiomorphism, diastereoisomerism, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 328.
Molecular Properties / Structure |
Enantiomers |
Diastereomers |
Constitutional Isomers
Aspects of isomerism and mesomerism. II. Structural isomerism  Bent, Richard L.
Examines the relationship between structural, optical, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 284.
Molecular Properties / Structure |
Constitutional Isomers |
Enantiomers |
Diastereomers