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The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder ReactionXavier 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
Determination of the Rotational Barrier for Kinetically Stable Conformational Isomers via NMR and 2D TLCGregory 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.
Azulene ChemistryWilliam F. Coleman The month's featured molecules come from the paper An Azulene-Based Discovery Experiment: Challenging Students To Watch for the "False Assumption" by Charles Garner illustrating some of the chemistry of a substituted azulene. Azulene is a structural isomer of naphthalene and differs from it in several important ways, the most obvious being azulene's intense blue color, which arises from the S0 → S2 transition. Another unusual feature of this molecule is that its fluorescence arises from the reverse of this transition rather than from S1 → S0.
Molecular Modeling |
Molecular Properties / Structure
AlkanesEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Alkanes / Cycloalkanes
CycloalkanesEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
