Selective thiourea optical probe based on thiourea-induced removal of chloroacetyl group from chloroacetylamine

Spectrochim Acta A Mol Biomol Spectrosc. 2006 Dec;65(5):1063-8. doi: 10.1016/j.saa.2006.02.012. Epub 2006 Jul 7.

Abstract

A novel chromogenic probe for thiourea, N-chloroacetyl parafuchsin (CAP), was designed and synthesized. The method was based on the reaction of CAP with thiourea, resulting in the initial formation of the S-substituted thioformamidine hydrochloride, which would then undergo the intramolecular amidinolysis to liberate the corresponding amine, and thus leading to an absorbance increase at visible spectral range. Based on this mechanism, a highly selective optical probe for thiourea was developed. Under optimal conditions, absorbance increase (DeltaA) at 562 nm is proportional to thiourea concentration up to 0.2 mmolL(-1) with a detection limit of 2.1 micromolL(-1) (3sigma). Because of the selective removal of chloroacetyl group from CAP by thiourea, there is little interference by other molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemistry*
  • Chloroacetates*
  • Color
  • Hydrogen-Ion Concentration
  • Models, Biological
  • Solvents / chemistry
  • Spectrum Analysis
  • Temperature
  • Thiourea / pharmacology*
  • Time Factors
  • Trichloroacetic Acid / chemistry
  • Trityl Compounds / chemistry*

Substances

  • Acetamides
  • Chloroacetates
  • N-chloroacetyl parafuchsin
  • Solvents
  • Trityl Compounds
  • chloroacetamide
  • Trichloroacetic Acid
  • Thiourea