| Journal Articles: 34 results |
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The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction Xavier Sauvage and Lionel Delaude
Characterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.
Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ. 2008, 85, 1538.
Alkenes |
Aqueous Solution Chemistry |
Conformational Analysis |
Green Chemistry |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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A-DNA and B-DNA: Comparing Their Historical X-ray Fiber Diffraction Images Amand A. Lucas
This paper provides a comparative explanation of the structural content of the diffraction diagrams of A-DNA and B-DNA that facilitated the discovery of the double-helical structure of DNA by Watson and Crick in 1953. This analysis is supported a method that simulates both A-DNA and B-DNA X-ray images optically.
Lucas, Amand A. J. Chem. Educ. 2008, 85, 737.
Biophysical Chemistry |
Conformational Analysis |
Crystals / Crystallography |
X-ray Crystallography |
Nucleic Acids / DNA / RNA
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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
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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 CarylNimidesingle 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
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A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. An Advanced Undergraduate Project in Organic Synthesis and Structural Analysis Lionel Delaude, Jean Grandjean, and Alfred F. Noels
The Robinson annulation is a three-step process involving a Michael addition followed by an internal aldol condensation and a dehydration. It is possible to stop the reaction after every step and to isolate the three products, allowing students to confirm the validity of the stepwise mechanism and develop a more thorough understanding of the whole process.
Delaude, Lionel; Grandjean, Jean; Noels, Alfred F. J. Chem. Educ. 2006, 83, 1225.
Catalysis |
Chirality / Optical Activity |
Conformational Analysis |
Diastereomers |
IR Spectroscopy |
Synthesis |
NMR Spectroscopy |
Stereochemistry
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Synthesis and Cytotoxic Properties of Chalcones: An Interactive and Investigative Undergraduate Laboratory Project at the Interface of Chemistry and Biology John Dickson, Lloyd Flores, Michelle Stewart, Regan LeBlanc, Hari N. Pati, Moses Lee, and Herman Holt
This project combines the synthesis of a small library of 30 appropriately substituted chalcones, the measurement of their cytotoxic properties, and the study of their structureactivity relationships using computational chemistry.
Dickson, John; Flores, Lloyd; Stewart, Michelle; LeBlanc, Regan; Pati, Hari N.; Lee, Moses; Holt, Herman. J. Chem. Educ. 2006, 83, 934.
Biotechnology |
Combinatorial Chemistry |
Conformational Analysis |
Medicinal Chemistry |
Molecular Modeling |
Natural Products |
Synthesis
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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
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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 ahydroxyketones 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
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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
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Following Microscale Organic Reactions Using FT-IR Janice Ems-Wilson
This article describes an experiment that encourages discussion of carbohydrate chemistry in terms of reaction mechanisms, conformational analysis, and spectroscopy. The specific experiment involves the preparation of the bis(acetonide) of D-(+)-mannose.
Ems-Wilson, Janice. J. Chem. Educ. 1996, 73, A170.
Microscale Lab |
Carbohydrates |
Mechanisms of Reactions |
Conformational Analysis |
Spectroscopy |
Synthesis |
Aldehydes / Ketones |
Alcohols
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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
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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
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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
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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
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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
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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
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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
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Chain Structure and Conformation of Macromolecules (Bovey, Frank A.; Jelinski, Lynn W.) Carraher, Charles E., Jr.
The first seven chapters are based on lectures delivered in 1981 at MIT.
Carraher, Charles E., Jr. J. Chem. Educ. 1984, 61, A209.
Molecular Properties / Structure |
Stereochemistry |
Conformational Analysis |
NMR Spectroscopy
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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
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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
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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
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Computer-assisted instruction in stereochemical configuration analysis Bishop, Marvin; Nowak, Maria
Bishop, Marvin; Nowak, Maria J. Chem. Educ. 1979, 56, 318.
Molecular Properties / Structure |
Stereochemistry |
Conformational Analysis |
Nomenclature / Units / Symbols
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Cheaply constructed models for conformation studies Jagannathan, K.
Instructions for building models for conformation studies.
Jagannathan, K. J. Chem. Educ. 1976, 53, 47.
Conformational Analysis |
Molecular Modeling
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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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