| Journal Articles: 17 results |
|
|
The Resolution of Ibuprofen, 2-(4′-Isobutylphenyl)propionic Acid James V. McCullagh
In this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-a-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments.
McCullagh, James V. J. Chem. Educ. 2008, 85, 941.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enantiomers |
Quantitative Analysis |
Separation Science
|
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
|
Showing Enantiomorphous Crystals of Tartaric Acid Julio Andrade-Gamboa
Most drawings of enantiomorphous crystals are inadequate to demonstrate that they are non-superimposable mirror images. This article examines the classic case of tartaric acid and the use of an alternative graphical representation and a paper model to facilitate the conceptualization of this subject.
Andrade-Gamboa, Julio. J. Chem. Educ. 2007, 84, 1783.
Chirality / Optical Activity |
Crystals / Crystallography |
Enantiomers |
Stereochemistry
|
Isolation of Three Components from Spearmint Oil: An Exercise in Column and Thin-Layer Chromatography Don R. Davies and Todd M. Johnson
In this exercise, the three major components of spearmint oil, (+)-limonene, L-(-)-carvone, and (1R,2R,4R)-dihydrocarveol, are separated by silica gel column chromatography. The separation is monitored by thin-layer chromatography, and IR analysis is employed to verify the identity of the separated components.
Davies, Don R.; Johnson, Todd M. J. Chem. Educ. 2007, 84, 318.
Chirality / Optical Activity |
Chromatography |
Natural Products |
Microscale Lab |
Thin Layer Chromatography |
Separation Science
|
Cotton Effect in Copper–Proline Complexes in the Visible Region Victor Volkov and Rolf Pfister
This article suggests taking advantage of the visible dd 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
|
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
|
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
|
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis
|
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
|
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
|
Lecture demonstrations for organic/ biochemistry allied health courses Deavor, James P.
Simple demonstrations on enantiomeric pairs and protein structure.
Deavor, James P. J. Chem. Educ. 1988, 65, 622.
Enantiomers |
Chirality / Optical Activity |
Proteins / Peptides |
Nonmajor Courses |
Amino Acids
|
The spontaneous resolution of cis-bis(ethylenediamine)dinitrocobalt(III) salts: Alfred Werner's overlooked opportunity Bernal, Ivan; Kauffman, George B.
Geometric isomerism and proof of the octahedral configuration; optical isomerism and proof of the octahedral configuration; and the spontaneous resolution of coordination compounds.
Bernal, Ivan; Kauffman, George B. J. Chem. Educ. 1987, 64, 604.
Coordination Compounds |
Women in Chemistry |
Chirality / Optical Activity
|
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
|
Rediscovery in a course for nonscientists. Use of molecular models to solve classical structural problems Wood, Gordon W.
Describes exercises using simple ball and stick models that students with no chemistry background can solve in the context of the original discovery.
Wood, Gordon W. J. Chem. Educ. 1975, 52, 177.
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Nonmajor Courses
|
Molecular symmetry and optical inactivity Carlos, Jose L., Jr.
Presents a criterion for optical inactivity that is both sufficient and easily applicable.
Carlos, Jose L., Jr. J. Chem. Educ. 1968, 45, 248.
Molecular Properties / Structure |
Chirality / Optical Activity
|
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
|
|
