SOLVATION AND METAL-ION EFFECTS ON STRUCTURE AND REACTIVITY OF PHOSPHORYL COMPOUNDS .1. BETA-SUBSTITUTED ALKYLPHOSPHONIC ESTERS

被引：21

作者：

BELCIUG, MP ^{[1
]}

MODRO, AM ^{[1
]}

MODRO, TA ^{[1
]}

WESSELS, PL ^{[1
]}

机构：

[1] UNIV PRETORIA,DEPT CHEM,PRETORIA 0002,SOUTH AFRICA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1992年 / 5卷 / 12期

关键词：

D O I：

10.1002/poc.610051203

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NMR spectroscopic and conformational analyses were performed for three beta-substituted beta-phenylethylphosphonic esters, PhCHXCH2PO3Me2 (X = OH, OMe, Cl) in five solvents and in acetone containing sodium and magnesium salts. Strong attractive interactions between the phosphoryl group and the oxygen-containing substituent X were demonstrated, and were shown to involve intramolecular hydrogen bonding, donor-acceptor O --> P effect and the chelation of a metal ion. These effects led to marked selectivity in the population of individual conformations of the phosphonates. The analogous intramolecular effects were found to be much weaker in the corresponding carboxylic ester systems.

引用

页码：787 / 794

页数：8

共 39 条

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