On the Basicity of Organic Bases in Different Media

The basicities of simple organic bases – aliphatic and aromatic amines, amidines, phosphazenes, as well as saturated and unsaturated nitrogen heterocycles – are examined in acetonitrile, dimethyl sulfoxide, tetrahydrofuran, water and the gas phase. The basicities (pKaH values) of conjugate acids of...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-10, Vol.2019 (40), p.6735-6748
Main Authors: Tshepelevitsh, Sofja, Kütt, Agnes, Lõkov, Märt, Kaljurand, Ivari, Saame, Jaan, Heering, Agnes, Plieger, Paul G., Vianello, Robert, Leito, Ivo
Format: Article
Language:English
Subjects:
Acetonitrile
Aliphatic compounds
Amines
Basicity
Conjugate acids
Dimethyl sulfoxide
Nitrogen bases
Non‐aqueous solvents
Solvent effects
Solvents
Tetrahydrofuran
Vapor phases
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Summary:The basicities of simple organic bases – aliphatic and aromatic amines, amidines, phosphazenes, as well as saturated and unsaturated nitrogen heterocycles – are examined in acetonitrile, dimethyl sulfoxide, tetrahydrofuran, water and the gas phase. The basicities (pKaH values) of conjugate acids of a large variety of bases in these media are presented and discussed. Equations employing easily usable structural descriptors have been derived for approximately converting basicities from acetonitrile to other solvents. Recommendations are given on their practical use and a number of pKaH values that are experimentally unavailable are estimated from these relationships. An important part of the minireview is a large compilation of pKaH and GB values of the compounds in solvents and the gas phase, respectively, as well as the revised basicity scale in acetonitrile, now containing more than 270 pKaH values. Basicity values for simple nitrogen bases in different solvents and in the gas phase were compiled and discussed. The self‐consistent basicity scale in acetonitrile was updated and expanded to contain 279 compounds. Simple equations for conversion of the pKaH values from acetonitrile to other solvents have been formulated and discussed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900956