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Journal Articles: 44 results
Percy Julian, Robert Robinson, and the Identity of Eserethole  Addison Ault
The Nova production Percy Julian┬ŁForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered.
Ault, Addison. J. Chem. Educ. 2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
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┬Ła 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
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
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
"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
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
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
Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid  Steven C. Cermak and David F. Wiemer
The preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments.
Cermak, Steven C.; Wiemer, David F. J. Chem. Educ. 1999, 76, 1715.
Stereochemistry |
Synthesis |
Aromatic Compounds |
Ethers |
Alcohols |
Aldehydes / Ketones |
Acids / Bases
Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity  Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
Synthesis |
Catalysis |
Stereochemistry |
Organometallics |
Molecular Properties / Structure
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
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
Incorporating Heterotopicity into Organic Chemistry  Thall, Edwin
This paper reviews topological relationships and suggests how to incorporate heterotopic concepts into the contemporary chemistry curriculum.
Thall, Edwin J. Chem. Educ. 1994, 71, 1034.
Stereochemistry |
Crystal Field / Ligand Field Theory
Models of 2-Butanone: Using Graphics To Illustrate Complementary Approaches to Molecular Structure and Reactivity  Hanks, T. W.
157. Ways in which a graphics workstation can be used to illustrate various concepts of molecular structure.
Hanks, T. W. J. Chem. Educ. 1994, 71, 62.
Aldehydes / Ketones |
Molecular Properties / Structure |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Stereochemistry |
Quantum Chemistry |
MO Theory
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
Optical activity can be created from "nothing"  Caswell, Lesley; Garcia-Garibay, Miguel A.; Scheffer, John R.; Trotter, James
Optically active products can be generated from achiral reactants.
Caswell, Lesley; Garcia-Garibay, Miguel A.; Scheffer, John R.; Trotter, James J. Chem. Educ. 1993, 70, 785.
Enantiomers |
Stereochemistry
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
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
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
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
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
Stereoisomerism as a result of free radical chlorination of a nonstereoisomeric substance  Fulkroad, John E.
Examples of questions and solutions regarding stereoisomerism as a result of free radical chlorination of a nonstereoisomeric substance.
Fulkroad, John E. J. Chem. Educ. 1987, 64, 533.
Stereochemistry |
Free Radicals
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
Configurations of glucose and other aldoses: New twists and reflections an old problems  Bentley, Ronald; Popp, Janet L.
Develops a comprehensive treatment of the configurations of aldoses in terms of the concept of rotational symmetry.
Bentley, Ronald; Popp, Janet L. J. Chem. Educ. 1987, 64, 15.
Carbohydrates |
Stereochemistry |
Molecular Properties / Structure
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 novel method for assigning R, S labels to enantiomers  Huheey, James E.
A procedure is suggested to provide students with greater insight into the properties of dissymmetrical molecules.
Huheey, James E. J. Chem. Educ. 1986, 63, 598.
Enantiomers |
Stereochemistry
Stress the twofold axis of the threo isomer  Tavernier, D.
The author weighs in on the the controversy of the threo and erythro nomenclature.
Tavernier, D. J. Chem. Educ. 1986, 63, 511.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Diastereomers
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
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
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
"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
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
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
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
Selectivity and specificity in organic reactions  Ault, Addison
Distinguishes between various forms of selectivity and specificity (e.g. the us of and differences between stereoselective and stereospecific).
Ault, Addison J. Chem. Educ. 1977, 54, 614.
Reactions |
Stereochemistry |
Diastereomers |
Enantiomers |
Nomenclature / Units / Symbols
The octant rule: Its place in organic stereochemistry  Murphy, William S.
Considers optical rotatory dispersion and circular dichroism, the Cotton effect and the octant rule, and applications of the octant rule.
Murphy, William S. J. Chem. Educ. 1975, 52, 774.
Stereochemistry |
Molecular Properties / Structure |
Conformational Analysis
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
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
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
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
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