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Lithium Amides: Intra‐Aggregate Complexation of Lithium and Entropy Control of Basicity
Author(s) -
van Vliet Gerbert L. J.,
Luitjes Henri,
Schakel Marius,
Klumpp Gerhard W.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000502)39:9<1643::aid-anie1643>3.0.co;2-9
Subject(s) - conjugate , chemistry , triphenylmethane , lithium (medication) , alkyl , entropy (arrow of time) , molecule , medicinal chemistry , organic chemistry , inorganic chemistry , thermodynamics , mathematics , physics , medicine , mathematical analysis , endocrinology
Entropy effects play a major role in determining the basicity of lithium amides. The negative value of Δ S for the reaction of (alkyl)(methyl)amino‐substituted lithium amides such as 1 with triphenylmethane results from the immobilization of THF molecules by complexation. The p K value of the conjugate base of 1 is 4.3 units lower than that of Me 2 NH.