| Journal Articles: 52 results |
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The Meaning of Meso Addison Ault
The original use of the prefix "meso" was to refer to an optically inactive, non-resolvable member of a set of stereoisomers, some of which were optically active.
Ault, Addison. J. Chem. Educ. 2008, 85, 441.
Chirality / Optical Activity |
Stereochemistry
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A Simple Method for Drawing Chiral Mononuclear Octahedral Metal Complexes Aminou Mohamadou and Arnaud Haudrechy
This article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties.
Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ. 2008, 85, 436.
Asymmetric Synthesis |
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements
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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 GCMS, 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
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Precision in Stereochemical Terminology LeRoy G. Wade, Jr.
This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.
Wade, LeRoy G., Jr. J. Chem. Educ. 2006, 83, 1793.
Chemical Technicians |
Diastereomers |
Enantiomers |
Stereochemistry |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
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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
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Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
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An Engaging Illustration of the Physical Differences among Menthol Stereoisomers Edward M. Treadwell and T. Howard Black
The differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (-)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed.
Treadwell, Edward M.; Black, T. Howard. J. Chem. Educ. 2005, 82, 1046.
Chirality / Optical Activity |
Stereochemistry |
Thin Layer Chromatography |
Diastereomers |
Enantiomers |
Physical Properties
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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
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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
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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
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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
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"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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Introduction to stereochemistry (Mislow, Kurt) Petersen, Quentin R.
Petersen, Quentin R. J. Chem. Educ. 1966, 43, A272.
Stereochemistry
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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
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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
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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
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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
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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
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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
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