Potentiometric Investigation of the Effects of Several Substituents on the Basicity of Benzilidene-o-hydroxyaniline

Authors

Esma KILIÇ
Orhan ATAKOL
E. CANEL
Zehra ALİBEŞEOĞLU
Turgut GÜNDÜZ
Fitnat KÖSEOĞLU

DOI

-

Abstract

Chloro-, bromo-, iodo-, nitro-, methoxy- and hydroxy-substituted benzilidene-o-hydroxyaniline were prepared in order to investigate the effects of substituents on the basicity of benzilidene-o-hydroxyaniline. For each substituent, three isomers -- ortho, meta and para -- were synthesised. Schiff bases were titrated potentiometrically with perchloric acid in nitrobenzene solvent at $25^{\circ}$C. All compounds gave well-shaped titration curves, from which half-neutralisation potentials were calculated. The trend in the values of half-neutralisation potentials of Schiff bases were explained in terms of the nature of the substituents. The applicability of the Hammett equation to the effect of substituents in Schiff bases in nitrobenzene solvent was discussed.

Keywords

Schiff bases, nonaqueous media, substituent effect, potentiometric titration.

First Page

387

Last Page

392

Recommended Citation

KILIÇ, Esma; ATAKOL, Orhan; CANEL, E.; ALİBEŞEOĞLU, Zehra; GÜNDÜZ, Turgut; and KÖSEOĞLU, Fitnat (1998) "Potentiometric Investigation of the Effects of Several Substituents on the Basicity of Benzilidene-o-hydroxyaniline," Turkish Journal of Chemistry: Vol. 22: No. 4, Article 11. Available at: https://journals.tubitak.gov.tr/chem/vol22/iss4/11