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Study of E/Z isomerization of (arylamino)methylidenefuran‐2( 3H )‐ones by 1 H, 13 C, 15 N spectroscopy and DFT calculations in different solvents
Author(s) -
Osipov Alexander K.,
Anis'kov Alexander A.,
Grinev Vyacheslav S.,
Yegorova Alevtina Yu.
Publication year - 2017
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.4583
Subject(s) - chemistry , isomerization , density functional theory , spectroscopy , nuclear magnetic resonance spectroscopy , computational chemistry , resonance (particle physics) , heteronuclear single quantum coherence spectroscopy , chemical shift , crystallography , analytical chemistry (journal) , stereochemistry , atomic physics , organic chemistry , quantum mechanics , physics , catalysis
The structure and configuration of the series of previously unknown arylaminomethylidenefuran‐2(3 H )‐ones have been determined in solution by 1 H, 13 C, 15 N nuclear magnetic resonance spectroscopy including two‐dimensional experiments such as 1 H─ 1 H COSY, dqCOSY, 1 H─ 13 C HSQC, 1 H─ 13 C HMBC. It was found that synthesized substances exist as an equilibrium mixture of E ‐ and Z ‐enamines in solution. It was established on the basis of density functional theory calculations that the exchange between the two push–pull enamines is a simple rotation around an exocyclic partial double bond that depends on the effect of the solvents. Copyright © 2017 John Wiley & Sons, Ltd.