Reactions of phosphate and phosphorothiolate diesters with nucleophiles: comparison of transition state structures

JD Ye, CD Barth, PSR Anjaneyulu, T Tuschl…

文献索引：Ye, Jing-Dong; Barth, Christofer D.; Anjaneyulu, Potluri S. R.; Tuschl, Thomas; Piccirilli, Joseph A. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 15 p. 2491 - 2497

全文：HTML全文

被引用次数: 14

摘要

A series of methyl aryl phosphorothiolate esters (SP) were synthesized and their reactions with pyridine derivatives were compared to those for methyl aryl phosphate esters (OP). Results show that SP esters react with pyridine nucleophiles via a concerted SN2 (P) mechanism. Brønsted analysis suggests that reactions of both SP and OP esters proceed via transition states with dissociative character. The overall similarity of the transition state ...