Basicities of cycloalkylamines: Baeyer strain theory revisited

被引：29

作者：

Perrin, CL ^{[1
]}

Fabian, MA ^{[1
]}

Rivero, IA ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 18期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

amines; basicity; strained compounds; solvents and solvent effects;

D O I：

10.1016/S0040-4020(99)00242-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, accurate NMR titration method was utilized to determine relative basicities in four solvents of the two norbornylamines 2 and a series of cycloalkylamines 3-15, as well as some sec-alkyl amines. Cyclopentylamine (5) and cyclohexylamine (6) are substantially more basic than the small rings 3-4 and slightly less basic than the medium rings 7-11, with cyclooctylamine (8) the most basic. The large rings 12-15 are significantly less basic than 6. The basicities reflect CCC angles, hybridization, and also solvation. These results and their relationship to Baeyer strain theory are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5773 / 5780

页数：8

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