| Journal Articles: 39 results |
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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 centurya 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
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Synthesis of Anomeric Methyl Fructofuranosides and Their Separation on an Ion-exchange Resin Erkki Nurminen, Päivi Poijärvi, Katja Koskua, and Jari Hovinen
Treatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl--d-fructopyranoside, methyl-a-D-fructofuranoside, and methyl--d- fructofuranoside, which are separated on an ion exchange column and characterized polarimetrically.
Nurminen, Erkki; Poijärvi, Päivi; Koskua, Katja; Hovinen, Jari. J. Chem. Educ. 2007, 84, 1480.
Carbocations |
Chirality / Optical Activity |
Chromatography |
Ion Exchange |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
Carbohydrates
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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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Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
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Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trans-b-Methylcinnamate Gayle J. Pageau, Rodwell Mabaera, Kathryn M. Kosuda, Tamara A. Sebelius, Ali H. Ghaffari, Kenneth A. Kearns, Jean P. McIntyre, Tina M. Beachy, and Dasan M. Thamattoor
Synthesis of the "strawberry aldehyde" epoxide, a well-known food and perfume additive.
Pageau, Gayle J.; Mabaera, Rodwell; Kosuda, Kathryn M.; Sebelius, Tamara A.; Ghaffari, Ali H.; Kearns, Kenneth A.; McIntyre, Jean P.; Beachy, Tina M.; Thamattoor, Dasan M. J. Chem. Educ. 2002, 79, 96.
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Epoxides |
Consumer Chemistry |
Food Science
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Demonstrating Chirality: Using a Mirror with Physical Models to Show Non-superimposability of Chiral Molecules with Their Mirror Images Michael J. Collins
Using a mirror with physical models to show non-superimposability of chiral molecules with their mirror images.
Collins, Michael J. J. Chem. Educ. 2001, 78, 1484.
Chirality / Optical Activity |
Enantiomers |
Molecular Modeling |
Molecular Properties / Structure
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The Other Double Helix--The Fascinating Chemistry of Starch Robert D. Hancock and Bryon J. Tarbet
The chemistry of starch, particularly the structure of starch and starch granules.
Hancock, Robert D.; Tarbet, Bryon J. J. Chem. Educ. 2000, 77, 988.
Bioorganic Chemistry |
Carbohydrates |
Food Science |
Stereochemistry |
Applications of Chemistry |
Molecular Properties / Structure
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Amyl: A Misunderstood Word Richard A. Kjonaas
There is much confusion associated with the word amyl. When younger chemists are taught to use the words propyl, butyl, and pentyl in place of n-propyl, n-butyl, and n-pentyl, they then incorrectly assume that this practice also applies to the word amyl.
Kjonaas, Richard A. J. Chem. Educ. 1996, 73, 1127.
Nomenclature / Units / Symbols
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Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
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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
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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
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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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Molecular structure and chirality (Author response) Lechner, Joseph H.
When right and left hands are perceived as isolated segments of the body, possessing a mirror-image relationship, with the understanding that they cannot be superimposed, then the true sense of chirality is imparted.
Lechner, Joseph H. J. Chem. Educ. 1990, 67, 358.
Chirality / Optical Activity |
Molecular Properties / Structure
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Molecular structure and chirality Brand, David J.
The statement that a pair of hands is "chiral" was misleading and would unnecessarily frustrate students.
Brand, David J. J. Chem. Educ. 1990, 67, 358.
Chirality / Optical Activity |
Molecular Properties / Structure
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Organic Reaction Chemistry, Review I (Flash, P.; Bendall, V.) Hargis, J. H.
Six different programs which allow the user to identify functional groups, supply the missing reagent necessary to complete a given reaction, deduce the product of a given reaction, ascertain whether a given reaction will go, search the reaction database for functional group conversions, and search for the utility of a certain reagent.
Hargis, J. H. J. Chem. Educ. 1989, 66, A170.
Reactions |
Enrichment / Review Materials |
Mechanisms of Reactions |
Nomenclature / Units / Symbols
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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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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
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Specification of R/S in a multichiral molecule (3) Aronson, John N.
Any system, simple or complex, cannot be used successfully to relate the R, S designations to Fischer projections if an incorrect two-dimensional projection is made of the three-dimensional model of the structure.
Aronson, John N. J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
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Specification of R/S in a multichiral molecule (2) Milakofsky, Louis
Suggested method has been presented before.
Milakofsky, Louis J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
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Specification of R/S in a multichiral molecule (1) Diehl, Justin W.
Suggested method becomes extremely difficult for a multichiral molecule.
Diehl, Justin W. J. Chem. Educ. 1984, 61, 90.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity
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Sulcatol: Synthesis of an aggregation pheromone Black, Shirley-Ann; Slessor, Keith N.
Synthesis of the aggregation pheromone of the ambrosia beetle, an insect pest of harvested timber in the Pacific North Coast.
Black, Shirley-Ann; Slessor, Keith N. J. Chem. Educ. 1982, 59, 255.
Synthesis |
Natural Products |
Molecular Properties / Structure |
Chirality / Optical Activity |
NMR Spectroscopy |
IR Spectroscopy |
Applications of Chemistry
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Use of hand models for assigning configurational nomenclature Garrett, James M.
A subject which often produces consternation in a beginning student in organic chemistry is that of sequential nomenclature involving chiral centers. After having studied the Cahn-Ingold-Prelog rules of nomenclature a student may be asked to examine a structure as shown in this article.
Garrett, James M. J. Chem. Educ. 1978, 55, 493.
Nomenclature / Units / Symbols |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
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A convenient notation for powers of ten and logarithms Oesterreicher, H.
A convenient notation for powers of ten and logarithms that does not require superscripts.
Oesterreicher, H. J. Chem. Educ. 1977, 54, 367.
Nomenclature / Units / Symbols
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Easily constructed models for demonstrating stereochemical nonrigidity in four- and six-coordinate complexes Levenson, Robert A.
Availability of templates and instructions for paper models that demonstrate stereochemical nonrigidity in four- and six-coordinate complexes.
Levenson, Robert A. J. Chem. Educ. 1975, 52, 386.
Stereochemistry |
Molecular Properties / Structure |
Molecular Modeling |
Coordination Compounds |
Transition Elements |
Metals
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The resolution of DL-histidine: An organic chemistry experiment using an ion exchange resin Bosch, Arthur J.
This experiment involves the isolation of the amino acid, D-histidine, from DL-histidine, and gives a product with high optical purity while demonstrating the use of an ion exchange resin and mixed solvent recrystallization.
Bosch, Arthur J. J. Chem. Educ. 1969, 46, 691.
Ion Exchange |
Amino Acids |
Chirality / Optical Activity |
Enantiomers
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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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Letters Fisher, D. Jerome
A spirited discussion regarding terminology for crystal classes.
Fisher, D. Jerome J. Chem. Educ. 1958, 35, 214.
Crystals / Crystallography |
Nomenclature / Units / Symbols
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Letters Donohue, Jerry
A spirited discussion regarding terminology for crystal classes.
Donohue, Jerry J. Chem. Educ. 1958, 35, 214.
Crystals / Crystallography |
Nomenclature / Units / Symbols
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Letters Fisher, D. Jerome
The author responds to criticism of his suggestions for naming classes of crystals.
Fisher, D. Jerome J. Chem. Educ. 1957, 34, 458.
Crystals / Crystallography |
Solids |
Nomenclature / Units / Symbols
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Letters to the editor Freedman, Jules
Commentary on the D and L convention as applied to tartaric acid.
Freedman, Jules J. Chem. Educ. 1957, 34, 362.
Acids / Bases |
Stereochemistry |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Enrichment / Review Materials |
Chirality / Optical Activity
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Letters to the editor Pickering, Roger A.
Commentary on the D and L convention as applied to tartaric acid.
Pickering, Roger A. J. Chem. Educ. 1957, 34, 362.
Stereochemistry |
Nomenclature / Units / Symbols |
Acids / Bases |
Molecular Properties / Structure |
Enantiomers |
Chirality / Optical Activity
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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
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Letters to the editor Donohue, Jerry
Commentary of the terminology of crystal classes.
Donohue, Jerry J. Chem. Educ. 1957, 34, 310.
Solids |
Crystals / Crystallography |
Nomenclature / Units / Symbols
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Assignment of D and L prefixes to the tartaric acids: The Wohl conventions Abernethy, John Leo
Examines the Wohl system for designating dextro- and levorotatory tartaric acids.
Abernethy, John Leo J. Chem. Educ. 1957, 34, 150.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Enantiomers |
Stereochemistry |
Chirality / Optical Activity |
Acids / Bases
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Assignment of D and L prefixes to the tartaric acids: An unsettled stereochemical question Nenitzescu, Costin D.
Examines the Wohl and Freudenberg systems of designating dextro- and levorotatory tartaric acids.
Nenitzescu, Costin D. J. Chem. Educ. 1957, 34, 147.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Acids / Bases |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
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Letters to the editor Gorin, George
Amplifies the discussion of proper configurational prefixes for the tartaric acids.
Gorin, George J. Chem. Educ. 1956, 33, 478.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity
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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
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A notation for the study of certain stereochemical problems Newman, Melvin S.
Newman introduces the projections of compounds containing two adjacent asymmetric carbons that would later bear his name.
Newman, Melvin S. J. Chem. Educ. 1955, 32, 344.
Nomenclature / Units / Symbols |
Stereochemistry |
Molecular Properties / Structure |
Conformational Analysis |
Chirality / Optical Activity
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