TIGER

Journal Articles: 40 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
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
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
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
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
"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
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
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
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
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
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
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
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 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
Stereochemistry and macromolecules: Principles and applications  Quirk, Roderic P.
This article was written to provide an introduction to the basic concepts of polymer stereochemistry and their applications.
Quirk, Roderic P. J. Chem. Educ. 1981, 58, 540.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
A helpful stereochemical instructional tool  England, Don
The figure found in this note has been helpful in aiding student understanding of stereochemistry.
England, Don J. Chem. Educ. 1981, 58, 31.
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Diastereomers |
Enantiomers
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
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
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
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
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
LTE. Rule of thumb for predicting optical activity  Mowery, Dwight F., Jr.
The author clarifies a point made in his earlier article.
Mowery, Dwight F., Jr. J. Chem. Educ. 1969, 46, 700.
Chirality / Optical Activity |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry
The 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
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
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