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Structure determination and conformation analysis of symmetrical dimers
Author(s) -
Buevich Alexei V.,
Chan TzeMing,
Wang C. H.,
McPhail Andrew T.,
Ganguly A. K.
Publication year - 2005
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/mrc.1526
Subject(s) - chemistry , vicinal , nuclear overhauser effect , stereochemistry , crystallography , proton , two dimensional nuclear magnetic resonance spectroscopy , proton nmr , nuclear magnetic resonance spectroscopy , physics , organic chemistry , quantum mechanics
Conformational and stereochemical analysis of six new symmetrical dimers was performed using proton–proton vicinal coupling measured from 1 H NMR and 13 C satellites of 1 H NMR signals, natural abundance 13 C‐edited nuclear overhauser effect (NOE) experiments, comprehensive NOE analysis and molecular modeling. The 13 C satellite analysis and 13 C‐edited NOE experiments were carried out to extract spectral information between equivalent protons. Molecular modeling was applied for estimations of three‐dimensional parameters of the studied dimers, which were subsequently used to generate a set of theoretical NOE for each possible conformation. The J ‐coupling, 13 C‐edited NOE and quantitative NOE analyses showed the predominance of gauche conformation for three dimers, whereas a mixture of gauche and anti conformations (45:55) for three other dimers was established by quantitative NOE analysis. X‐ray crystallographic study confirmed the stereochemistry of one of the dimers and revealed a discrepancy in conformation stability between liquid and solid states. Copyright © 2004 John Wiley & Sons, Ltd.