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Journal Articles: 32 results
Computational Analysis of Stereospecificity in the Cope Rearrangement  Laura Glish and Timothy W. Hanks
Experimental product distributions from the Cope rearrangement of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Visual analysis of these geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.
Glish, Laura; Hanks, Timothy W. J. Chem. Educ. 2007, 84, 2001.
Alkenes |
Computational Chemistry |
Conformational Analysis |
Medicinal Chemistry |
MO Theory |
Molecular Modeling |
Mechanisms of Reactions
Determination of the Rotational Barrier for Kinetically Stable Conformational Isomers via NMR and 2D TLC  Gregory T. Rushton, William G. Burns, Judi M. Lavin, Yong S. Chong, Perry Pellechia, and Ken D. Shimizu
After the synthesis of a N,N'-diaryl naphthalene diimide, students estimate the rotational barrier about a CarylNimidesingle bond by studying the reequilibration of the two resulting isomers using two-dimensional thin-layer chromatography, followed by a more accurate determination through a 1H NMR time study.
Rushton, Gregory T.; Burns, William G.; Lavin, Judi M.; Chong, Yong S.; Pellechia, Perry; Shimizu, Ken D. J. Chem. Educ. 2007, 84, 1499.
Alcohols |
Chromatography |
Conformational Analysis |
Equilibrium |
Kinetics |
NMR Spectroscopy |
Physical Properties |
Rate Law |
Thin Layer Chromatography
Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides  Jack R. Waas
Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides.
Waas, Jack R. J. Chem. Educ. 2006, 83, 1017.
Alkanes / Cycloalkanes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Reactions |
Reactive Intermediates |
Thermodynamics |
Elimination Reactions |
Nucleophilic Substitution
Computer-Based Conformational Analysis of Acetylcholine and Muscarine Combined with an Overview of the Receptor–Ligand Interaction   Marcelo Tavares de Oliveira, Minéia Alves dos Santos, and Thais Horta Álvares da Silva
Reports on a procedure to perform conformational analysis using the systematic search method and the superimposition of two bioactive molecules, acetylcholine and muscarine. The undergraduate students individually perform the proposed procedure using a personal computer.
Tavares de Oliveira, Marcelo; Alves dos Santos, Minéia ; Álvares da Silva, Thais Horta. J. Chem. Educ. 2006, 83, 780.
Bioorganic Chemistry |
Computational Chemistry |
Conformational Analysis |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Molecular Mechanics / Dynamics |
Molecular Modeling |
Molecular Properties / Structure |
Receptors
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 ahydroxyketones 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
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
Molecular Modeling of Non-Trivial Cyclohexane Derivatives: A Discovery Approach  Gail Horowitz
An experiment is described that utilizes molecular modeling to study the effects of sp2 hybridization, bond elongation, and heteroatom substitution upon the stabilities of the axial and equatorial conformers of cyclohexane.
Horowitz, Gail. J. Chem. Educ. 2004, 81, 1006.
Molecular Modeling |
Alkanes / Cycloalkanes |
Computational Chemistry |
Molecular Properties / Structure
The Conformational Behavior of n-Pentane: A Molecular Mechanics and Molecular Dynamics Experiment  Mencarelli, Paolo
174. Use of HyperChem to investigate the conformational behavior of n-pentane.
Mencarelli, Paolo J. Chem. Educ. 1995, 72, 511.
MO Theory |
Chirality / Optical Activity |
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Molecular Mechanics / Dynamics |
Molecular Modeling
Cyclooctane conformational analysis via mechanical and computational models  Fitzgerald, Jeffrey P.
Description of an exercise in which students use both mechanical and computational models to identify and quantify various types of strains in different conformations of a molecule.
Fitzgerald, Jeffrey P. J. Chem. Educ. 1993, 70, 988.
Molecular Modeling |
Alkanes / Cycloalkanes |
Diastereomers
An expanded Fieser model suitable for a large classroom  Levinson, Alfred S.; Zupan, Rudolph
In organic chemistry, one area in which models are indispensable is in introducing the conformational analysis of cyclopentane and cyclohexane rings.
Levinson, Alfred S.; Zupan, Rudolph J. Chem. Educ. 1992, 69, 369.
Alkanes / Cycloalkanes |
Molecular Modeling |
Molecular Properties / Structure
Molecular mechanics calculations of [3.3]metacyclophane  Biali, Silvio E.
121. Bits and pieces, 45. Cyclophane is an almost ideal system for a computational experiment since the molecule can can in principle exist is several conformations, yet, despite the conformational complexity, the molecule is of relative small size which enables fast calculation of the different conformations.
Biali, Silvio E. J. Chem. Educ. 1990, 67, 1038.
Molecular Mechanics / Dynamics |
Computational Chemistry |
Conformational Analysis
Use of polar maps in conformational analysis  Ounsworth, James P.; Weller, Larry
A relatively simple procedure to identify different or similar conformations of large ring structures (generating polar maps of torsional angles).
Ounsworth, James P.; Weller, Larry J. Chem. Educ. 1987, 64, 568.
Conformational Analysis |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Computer-assisted quantitative infrared conformational analysis of alpha, beta-unsaturated ketones  Tisnes, P.; Perry, M.
Investigates the s-cis <> s-trans conformational equilibrium of alpha, beta-unsaturated ketones.
Tisnes, P.; Perry, M. J. Chem. Educ. 1985, 62, 903.
Aldehydes / Ketones |
Conformational Analysis |
IR Spectroscopy |
Stereochemistry |
Molecular Properties / Structure |
Quantitative Analysis
Identification of the stable conformer of cyclohexane by vibrational spectroscopy  Garcia, M. V.; Redondo, M. I.
A laboratory experiment that uses group theory to help interpret infrared and Raman spectra of cyclohexane.
Garcia, M. V.; Redondo, M. I. J. Chem. Educ. 1985, 62, 887.
Alkanes / Cycloalkanes |
Spectroscopy |
Stereochemistry |
IR Spectroscopy |
Raman Spectroscopy |
Conformational Analysis |
Molecular Properties / Structure |
Group Theory / Symmetry
An introduction to conformational analysis of ethane and butane  Flash, Patrick J.
60. Bits and pieces, 23. Introduces students to some conventions for drawing molecules and provides a brief tutorial and extensive drill work on the conformations of ethane and butane.
Flash, Patrick J. J. Chem. Educ. 1985, 62, 412.
Conformational Analysis |
Alkanes / Cycloalkanes |
Enrichment / Review Materials
Using the QCPE holdings in chemical education: Molecular models in the organic chemistry laboratory  Lipkowitz, Kenny
A laboratory experiment that compares the strengths and weaknesses of mechanical and computer models.
Lipkowitz, Kenny J. Chem. Educ. 1984, 61, 1051.
Molecular Modeling |
Molecular Properties / Structure |
Conformational Analysis |
NMR Spectroscopy
A simple demonstration of conformational equilibrium  Partridge, D. A.
The infrared spectra of solutions of pinacol in tetrachloromethane with different molarities are compared to identify the presence of intermolecular hydrogen-bonding.
Partridge, D. A. J. Chem. Educ. 1980, 57, 508.
Equilibrium |
Molecular Properties / Structure |
Conformational Analysis |
Hydrogen Bonding |
IR Spectroscopy
Conformations of substituted ethanes  Kingsbury, Charles A.
Provides a state-of-the-art view of conformational analysis, with an emphasis on sp3 hybridized acyclic molecules.
Kingsbury, Charles A. J. Chem. Educ. 1979, 56, 431.
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Diastereomers
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
Conformational analysis - The last 25 years  Eliel, Ernest L.
Reviews the development of conformational analysis.
Eliel, Ernest L. J. Chem. Educ. 1975, 52, 762.
Conformational Analysis |
Molecular Properties / Structure
The boat form of cyclohexane as viewed by Midwestern sailors  Lyle, Gloria; Lyle, Robert E.
Possible confusion regarding the boat analogy in describing the positions of hydrogens in cyclohexane.
Lyle, Gloria; Lyle, Robert E. J. Chem. Educ. 1973, 50, 655.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Nomenclature / Units / Symbols
Simple equipment for measurement of dihedral angles on models  Leska, J.
Small, graduated rings situated along bonds in molecular models are used for conformational analysis.
Leska, J. J. Chem. Educ. 1973, 50, 516.
Molecular Modeling |
Conformational Analysis
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
Alicyclic chemistry: The playground for organic chemists  Ferguson, Lloyd N.
This article reviews a number of general topics that have been of special interest in alicyclic chemistry, including conformational analysis, the nonclassical versus classical norbornyl cation, Woodward-Hoffmann electrolytic rules, the aromaticity of nonbenzoid rings, strained ring systems, bridgehead activity, and photochemical syntheses and rearrangements.
Ferguson, Lloyd N. J. Chem. Educ. 1969, 46, 404.
Conformational Analysis |
Synthesis |
Photochemistry
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
Extensions in the use of plastic tetrahedral models  Fieser, Louis F.
Describes the modification of existing models to provide for the construction of specialized organic and inorganic structures and their use in teaching.
Fieser, Louis F. J. Chem. Educ. 1965, 42, 408.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Conformational analysis in the elementary organic course  Allinger, Norman L.
Examines the history of conformational analysis, examples of systems in which this analysis is important, and the use of current conformational analysis research in teaching.
Allinger, Norman L. J. Chem. Educ. 1964, 41, 70.
Conformational Analysis |
Molecular Properties / Structure
Cyclobutane chemistry. 1. Structure and strain energy  Wilson, Armin; Goldhamer, David
Examines the various conformations that have been proposed for particular four-membered rings.
Wilson, Armin; Goldhamer, David J. Chem. Educ. 1963, 40, 504.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
Lecture demonstration models of cycloalkanes  Schultz, Harry P.
Describes large, sturdy, lecture demonstration models of cycloalkanes.
Schultz, Harry P. J. Chem. Educ. 1962, 39, 648.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Recent advances in stereochemistry: A survey  Cram, Donald J.
The purpose of this article is to provide illustrations of eight advances in stereochemistry, including absolute configuration, correlations between configuration and rotation, and conformational analysis.
Cram, Donald J. J. Chem. Educ. 1960, 37, 317.
Conformational Analysis |
Molecular Properties / Structure
Conformational analysis in mobile systems  Eliel, Ernest L.
A review of conformational analysis and its application to mobile systems.
Eliel, Ernest L. J. Chem. Educ. 1960, 37, 126.
Conformational Analysis |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
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