Influence of bond fixation in benzo-annulated n-salicylideneanilines and their ortho-C (O) X derivatives (x= CH3, NH2, OCH3) on tautomeric equilibria in solution

R Gawinecki, A Kuczek, E Kolehmainen…

Index: Gawinecki, Ryszard; Kolehmainen, Erkki; Kauppinen, Reijo Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1998 , # 1 p. 25 - 30

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Citation Number: 27

Abstract

1H, 13C, and 15N NMR spectra show that an ortho-C (O) X group present in the molecules of N-salicylideneanthranilamide (X= NH2), methyl N-salicylideneanthranilate (X= OCH3), N- salicylidene-o-aminoacetophenone (X= CH3), and their benzo analogues have only a minor effect on the tautomeric OH/NH-equilibrium in solution. Only two of three possible tautomers were detected. Lability of the absent form was proved by theoretical calculations. ...

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