Structure-stability correlations for imine formation in aqueous solution

被引：241

作者：

Godoy-Alcántar, C

Yatsimirsky, AK

Lehn, JM

机构：

[1] Univ Louis Pasteur Strasbourg 1, Inst Sci & Ingn Supramol, F-67083 Strasbourg, France

[2] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca 62210, Morelos, Mexico

[3] Univ Nacl Autonoma Mexico, Fac Quim, Mexico City 04510, DF, Mexico

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2005年 / 18卷 / 10期

关键词：

amine; aldehyde; imine formation; structure-stability correlations;

D O I：

10.1002/poc.941

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imine formation between 25 aldehydes and 13 amines in aqueous solution in the pH range 7-11 was studied by H-1 NMR spectroscopy. A three-parameter linear equation correlating logarithms of imine formation constants with pK(a) and HOMO energies of amines and LUMO energies of aldehydes is proposed. In view of the widespread occurrence of imine-forming processes in both chemistry and biology, the data presented are of significance for physical organic chemistry and of particular interest for dynamic combinatorial chemistry. Copyright (c) 2005 John Wiley & Sons, Ltd.

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页码：979 / 985

页数：7

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