SOLVATION AND METAL-ION EFFECTS ON STRUCTURE AND REACTIVITY OF PHOSPHORYL COMPOUNDS .2. BETA,GAMMA-SUBSTITUTED ALKYLPHOSPHONIC ESTERS

被引：6

作者：

BELCIUG, MP ^{[1
]}

MODRO, TA ^{[1
]}

WESSELS, PL ^{[1
]}

机构：

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

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1993年 / 6卷 / 09期

关键词：

D O I：

10.1002/poc.610060907

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NMR spectroscopic and conformation analyses ware carried out for five dimethyl beta,gamma-disubstituted propylphosphonates, YCH2CHXCH2PO3Me2, in five solvents and in acetone containing sodium and magnesium ions. Conformational preferences observed for the rotation about the C1-C2 bond are determined by the attractive interactions between the oxygen containing substituents X (X=OH, OMe) and the phosphoryl group, and are enhanced by the metal ions, presumably via chelation effects. The rotation about the C2-C3 bond yields statistical distribution of the rotamers. For Y = benzoyl, there was no evidence for a competition of the carbonyl group for the intramolecular interactions with X or with a metal ion.

引用

页码：523 / 530

页数：8

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