NMR of enaminones.: Part 6 -: 17O and 13C NMR study of tautomerization in Schiff bases

被引：0

作者：

Zhuo, JC ^{[1
]}

机构：

[1] Univ Lausanne, Inst Organ Chem, BCH, CH-1015 Lausanne, Switzerland

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 1999年 / 37卷 / 04期

关键词：

NMR; C-13; O-17; Schiff bases; tautomeric equilibrium;

D O I：

10.1002/(SICI)1097-458X(199904)37:4<259::AID-MRC442>3.0.CO;2-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

C-13 and O-17 NMR spectra are reported for three series of Schiff bases: 2-(aminomethylene)cyclohexanones (1), salicylideneamines (2) and N-(2-hydroxy-1-naphthalenylmethylene)amines (3). The C-13 and O-17 NMR data show that Schiff bases 1 exist in ketoenamine form, 2 in enolimine form and 3 as an equilibrium mixture of both forms. The tautomeric composition of Schiff base 3 was estimated. Alkylamines slightly favoured the ketoenamine form; aromatic amines favoured the enolimine form. The tautomeric equilibria are shifted towards the enolimine form in non-polar solvents and with increase in temperature.

引用

页码：259 / 268

页数：10

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