Mechanism of formation of biocidal imidazolidin-4-one derivatives: An ab initio density-functional theory

Akdag A. , Mckee M. L. , Worley S. D.

JOURNAL OF PHYSICAL CHEMISTRY A, vol.110, no.24, pp.7621-7627, 2006 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 110 Issue: 24
  • Publication Date: 2006
  • Doi Number: 10.1021/jp060879q
  • Page Numbers: pp.7621-7627


N-halamine chemistry has been a research topic of considerable importance in these laboratories for over 2 decades because N-halamine compounds are very useful in preparing biocidal materials. To understand the utility of these compounds, the stabilities and mechanism of halogenation of cyclic N-halamine compounds should be resolved. The important precursor biocidal compound, 2,2,5,5-tetramethylimidazolidin-4-one (TMIO) was considered as a model in this theoretical study. The thermodynamic and kinetic products of monohalogenation were investigated along with tautomerization of TMIO and succinimide theoretically at the level of B3LYP/6-311 + G(2d,p). Solvation effects (water and chloroform) were included using the CPCM solvation model with UAKS cavities. Several mechanisms have been proposed for the chlorine migration from the 3-position (kinetic product) to the 1-position (thermodynamic product) of the TMIO ring. The results are in agreement with experimental NMR data.