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A dynamic NMR study of Z , E ‐isomerization in solutions of indolyl‐substituted α‐nitroacrylates
Author(s) -
Bakhmutov V. I.,
Burmistrov V. A.,
Babievsky K. K.,
Kochetkov K. A.,
Kvasov B. A.,
Belikov V. M.,
Fedin E. I.
Publication year - 1978
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.1270110609
Subject(s) - isomerization , chemistry , nitrogen atom , ring (chemistry) , photochemistry , nuclear magnetic resonance spectroscopy , ion , medicinal chemistry , atom (system on chip) , stereochemistry , computational chemistry , organic chemistry , catalysis , computer science , embedded system
Fast Z , E ‐isomerization of α‐nitro‐β‐indolylacrylates in polar solvents has been studied by dynamic 1 H NMR spectroscopy. With indolylnitroacrylates having no substituents at the ring nitrogen atom, isomerization proceeds via intermediate formation of a mesomeric anion and ionization of the N–H bond as the rate determining step. For methyl‐substituted indolylnitroacrylates, no general isomerization mechanism can be suggested, and isomerization pathways depend on the structures of isomerizing species.