Acidity constant determination of novel drug precursor benzothiazolon derivatives including acyl and piperazine moieties

Spectrochim Acta A Mol Biomol Spectrosc. 2013 Jul:111:211-6. doi: 10.1016/j.saa.2013.03.071. Epub 2013 Mar 26.

Abstract

In this study, protonation and deprotonation behaviors of eight new drug precursor benzothiazolon derivatives in all of acidic and basic scale (super acidic, pH, super basic regions) are analyzed by using UV-visible spectrophotometric technique. Acidity constants (pKa), elucidation of the structure and protonation mechanisms of the studied molecules are obtained. Substituent effect on acidity constant values is discussed. These molecules are protonated from oxygen atom of acetamide group in the keto form. The protonation is found to be considerably contributed by the keto form.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Acylation
  • Benzothiazoles / chemistry*
  • Piperazine
  • Piperazines / chemistry*
  • Prodrugs / chemistry*
  • Protons
  • Solutions
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism

Substances

  • Acids
  • Benzothiazoles
  • Piperazines
  • Prodrugs
  • Protons
  • Solutions
  • Piperazine