Issue 8, 1980

Electrical effects in substituted thiazoles. pKa Values of some 5-substituted 2-aminothiazoles and 5-substituted 2-NN-dimethylaminothiazoles

Abstract

Comparison of the pKa values of some 5-X-aminothiazoles with those of the corresponding 5-X-2-NN-dimethylaminothiazoles allows the assignment of the aromatic amino form to 2-aminothiazole derivatives. A Hammett plot of pKa values against σmeta substituent constants is linear as required if the protonation centre is the endocyclic nitrogen in all cases. Cross-conjugation between the amino groups in position 2 and the substituents in position 5 is present only when the nitro-group is the substituent. Conjugative interaction between the amino group and the ‘aza’ group is also discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1980, 1156-1158

Electrical effects in substituted thiazoles. pKa Values of some 5-substituted 2-aminothiazoles and 5-substituted 2-NN-dimethylaminothiazoles

L. Forlani, P. De Maria and A. Fini, J. Chem. Soc., Perkin Trans. 2, 1980, 1156 DOI: 10.1039/P29800001156

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