Abstract
It is shown that the change of pKa of unsubstituted heterocyclic compounds on substitution is proportional to the difference of the residual π-electron charges at the position where the functional group is introduced in the unsubstituted heterobase and its conjugated acid.
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Translated from Teoreticheskaya i éksperimental'naya Khimiya, Vol. 24, No. 1, pp. 13–20, January–February, 1988.
The author expresses his gratitude to M. M. Mestechkin and N. G. Korzhenevskaya for the discussion.
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Vysotskii, Y.B. Quantum chemical study of the substituent effect on pKa of molecules with conjugated bonds using the PPP method. Theor Exp Chem 24, 12–18 (1988). https://doi.org/10.1007/BF01392184
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DOI: https://doi.org/10.1007/BF01392184