16000-61-6Relevant articles and documents
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Young,W.G. et al.
, p. 6163 - 6168 (1960)
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On the Basicity of Triarylmethylamines in Solution
Dahn, Hans,Farine, Jean-Claude,Nguyen, Thi Thanh Tam
, p. 780 - 787 (2007/10/02)
The pKa* of 11 triarylmethylamines (tritylamines), eight of which are new, and some related bases were measured in methylcellosolve/water 80:20 (MCS); some were also measured in dioxane/water 60:40 (Dx), acetonitrile (An), nitrobenzene (Nb) and acetic acid (Ac). 1) The influence of the aryl groups on the basicity is essentially additive; 2) In different solvents, similar linear free energy relationships were found, with differences in ρ* characteristic of solvation; 3) The influence on basicity of substituents of the aryl groups follows Hammett's relationship.These results indicate a preponderance of inductive effects.N,N-Dimethyltritylamine (3b) pKaMCS = 3.40) shows a marked crowding effect, absent in the isomeric tertiary amines 13 and 14.Tri-p-nitrotritylamine (10a) 8pKaMCS = 3.10), N,N-dimethyl-tri-p-nitrotritylamine (10b) (pKaAc = 0.50), and 3b are particularly weak bases; the baseweakenning effect of the trinitrotrityl group is similar to that of the cyanomethyl and trifluoroethyl groups.