Solvation and metal ion effects on structure and reactivity of phosphoryl compounds. 1. β-substituted alkylphosphonic esters

作者: Marie-P. Belciug , Agnes M. Modro , Tom A. Modro , Philippus L. Wessels

DOI: 10.1002/POC.610051203

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

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