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Synthesis, NMR and molecular modeling studies on the stereochemistry of 2‐aryl‐3‐(2′,4′‐dinitrophenylthio)cyclohexenes
Author(s) -
Devanathan V. C.,
Perumal S.,
Hewlins M. J. E.,
Ramalingam M.
Publication year - 2000
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/1097-458x(200006)38:6<463::aid-mrc660>3.0.co;2-9
Subject(s) - chemistry , conformational isomerism , aryl , cyclohexene , nuclear overhauser effect , ring (chemistry) , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , chemical shift , proton nmr , nmr spectra database , spectral line , carbon 13 nmr , computational chemistry , molecule , nuclear magnetic resonance spectroscopy , organic chemistry , catalysis , alkyl , physics , astronomy
Ten 2‐aryl‐3‐(2′,4′‐dinitrophenylthio)cyclohexenes were prepared, their 1 H NMR spectra measured and chemical shifts assigned on the basis of nuclear Overhauser enhancements, H,H‐COSY spectra and other considerations. Analysis of the data suggests the preference of the conformer with (i) the arylthio group in the axial orientation and (ii) the dinitrophenyl group oriented away from the cyclohexene ring. The NOE results and molecular modeling calculations also support the above conclusions. Copyright © 2000 John Wiley & Sons, Ltd.