The Journal of Organic Chemistry

Ion Pair Acidities and Aggregation of Some Amide and Oxazoline Enolates in THF

A Facchetti, A Streitwieser

Index: Facchetti, Antonio; Streitwieser, Andrew Journal of Organic Chemistry, 1999 , vol. 64, # 7 p. 2281 - 2286

Full Text: HTML

Citation Number: 17

Abstract

Equilibrium lithium ion pair acidities at 25° C have been determined in THF for the following acetamides: N, N-dimethyl-(4-biphenylyl) acetamide (1)(19.69), N, N-diethyl-(4-biphenylyl) acetamide (2)(20.30), N, N-dimethyl-diphenylacetamide (3)(20.76), N, N-diethyl- diphenylacetamide (4)(21.99), and 1-(diphenylmethylcarbonyl) pyrrolidine (5)(21.08). These acidity data compare well with those previously reported for the corresponding cesium ...