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A 1 H NMR study of tautomerism in some 1‐arylamino‐3‐aryliminopropenes
Author(s) -
Richards C. P.,
Webb G. A.
Publication year - 1976
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270080409
Subject(s) - tautomer , chemistry , cis–trans isomerism , coupling constant , hydrogen bond , derivative (finance) , nmr spectra database , spectral line , nuclear magnetic resonance spectroscopy , computational chemistry , medicinal chemistry , stereochemistry , molecule , organic chemistry , physics , economics , particle physics , astronomy , financial economics
1 H n.m.r. spectra at ambient temperatures reveal that an equilibrium exists between the ‘all‐ trans ’ and ‘all‐ cis ’ isomers of some of the 1‐arylamino‐3‐aryliminopropenes. The ‘all‐ cis ’ isomer predominates in nonpolar solvents, whereas the ‘all‐ trans ’ isomer is favoured in hydrogen bonding solvents. From a consideration of the magnitudes of the 3 J coupling constants, it is reported that the ‘ cis ‐ trans ’ isomer is the most stable form of the 4‐nitrophenyl derivative in dimethyl sulphoxide.