pK(a) Determination of Newly Synthesized N-(benzothiazole-2-yl)-2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)acetamide Derivatives

DURAN M., CANBAZ M.

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, vol.52, no.25, pp.8355-8360, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 52 Issue: 25
  • Publication Date: 2013
  • Doi Number: 10.1021/ie400316r
  • Journal Name: INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.8355-8360
  • Eskisehir Osmangazi University Affiliated: Yes

Abstract

In this work, nine drug precursors, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(benzothiazole-2yl) acetamide derivative compounds, were newly synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with 2-chloro-N-(thiazol-2-yl) acetamide compounds. Structures of the synthesized compounds were confirmed by H-1 NMR, FTIR (Fourier transform infrared), MS (mass spectroscopy), and elemental analysis. The acidity constants of these acetamide derivatives were determined via UV spectroscopic studies. It was found that the first protonation of these compounds occurs on the nitrogen at imidazole ring, while the second protonation of these compounds occurs on the nitrogen at benzothiazole ring. The first pK(a) values were found to vary between 5.91 and 8.34 while the second pK(a) values were varying between 3.02 and 4.72.