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Molecular structures of regioisomeric 7‐arylidene hexahydroindazoles from 1 H NMR spectra
Author(s) -
Pivnenko Nikolay S.,
Turov Alexander V.,
Abakumov Vladimir V.,
Kutulya Lidiya A.,
Shishkina Svetlana V.,
Shishkin Oleg V.
Publication year - 2009
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.2421
Subject(s) - chemistry , density functional theory , nuclear overhauser effect , nmr spectra database , chemical shift , computational chemistry , coupling constant , carbon 13 nmr , two dimensional nuclear magnetic resonance spectroscopy , molecule , proton nmr , liquid crystal , spectral line , hydrazine (antidepressant) , stereochemistry , nuclear magnetic resonance spectroscopy , crystallography , organic chemistry , physics , particle physics , chromatography , astronomy , optics
The structural characterization of two regioisomeric products of the interaction of 2,6‐bis‐(4‐methoxybenzylidene)‐3 R ‐methylcyclohexanone with methyl hydrazine was achieved using 1 H NMR spectral data, including chemical shifts, coupling constants and results of COSY and nuclear overhauser effect (NOE) experiments. Configurations of the new chiral centers in the (3 S ,3a R ,6 R ,7 E )‐7‐(4‐methoxybenzylidene)‐3,4,5,7‐hexahydro‐3‐(4‐methoxyphenyl)‐2,6‐dimethyl‐ and 2,4‐dimethyl‐2 H ‐indazoles were assigned on the basis of experimental data combined with molecular modeling by the density functional theory (DFT) method. The distinction in the helical twisting power of studied compounds under addition to a nematic liquid crystal is discussed on the basis of peculiarities of the molecular structures. Copyright © 2009 John Wiley & Sons, Ltd.