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Differential rates of NH proton exchange reactions of two isomeric enamines
Author(s) -
Yavari Issa,
HosainNia Azar
Publication year - 1992
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.1260300511
Subject(s) - chemistry , proton , base (topology) , proton nmr , spectral line , nmr spectra database , medicinal chemistry , computational chemistry , stereochemistry , mathematical analysis , physics , mathematics , quantum mechanics , astronomy
Proton NMR spectra of ( E )‐ and ( Z )‐[1,2‐bis(methoxycarbonyl)vinyl]aminotoluene were obtained in neutral and basic solutions at 25°C. Base‐catalysed NH proton exchange of the E isomer was found to be about 50 times faster than for the Z isomer. The results are rationalized by consideration of electronic and hydrogen bonding effects.
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