Solvent Effects on pK(a) values of Some Substituted Sulfonamides in Acetonitrile-Water Binary Mixtures by the UV-Spectroscopy Method

Sanli S., Altun Y., Sanli N., Alsancak G., Beltran J. L.

JOURNAL OF CHEMICAL AND ENGINEERING DATA, cilt.54, sa.11, ss.3014-3021, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 54 Sayı: 11
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1021/je9000813
  • Dergi Adı: JOURNAL OF CHEMICAL AND ENGINEERING DATA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3014-3021
  • Gazi Üniversitesi Adresli: Evet

Özet

The examination of the dissociation constants of sulfonamides is essential in drug-design studies and in explaining the biopharmaceutical properties of substances. The dissociation constants of ten common human and veterinary antibiotics, namely, sulfadiazine, sulfamerazine, sulfamethoxazole, sulfathiazole, sulfamonomethoxine, sulfamethoxypyridazine, sulfadimethoxine, sulfafurazole, sulfadoxine, and sulfaquinoxaline, in water and in 15 %, 23 %, and 30 % (v/v) acetonitrile-water mixtures were determined by a UV/pH titration method and correlated with the Kamlet and Taft solvatochromic parameters, pi*, alpha, and beta. Kamlet and Taft's general equation was reduced to two terms by combined factor analysis and target factor analysis in these mixtures: the independent term and polarity/polafizability pi*, which is a solvatochromic parameter. Further, the quasi-lattice quasi-chemical (QLQC) theory of preferential solvation has been applied to quantify the preferential solvation by water of electrolytes in acetonitrile-water mixtures.