Basicity of substituted 2-pyridyl-1,1,3,3-tetramethylguanidines and aminopyridines in acetonitrile and water solvents
- 1 December 1992
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 70 (12) , 2856-2858
- https://doi.org/10.1139/v92-363
Abstract
A series of substituted 2-pyridyl-1,1,3,3-tetramethylguanidines has been synthesized and the pKa of each has been measured in acetonitrile and water solvents, together with the pKa of the corresponding aminopyridine. A relationship between the pKa's in these two solvents has been derived that allows the estimation of a pKa in acetonitrile from that in water. The results were fitted to the Hammett equation, giving ρ = 2.31 ± 0.14 and 1.64 ± 0.11 for the pyridylguanidines in acetonitrile and water, respectively, and 6.16 ± 0.4 and 5.24 ± 0.2 for the aminopyridines in the same solvents.Keywords
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