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
收藏
页码：259 / 268
页数：10
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