The stabilities of N-Cl bonds in biocidal materials

Akdag A., Okur S., McKee M. L., Worley S. D.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, vol.2, no.3, pp.879-884, 2006 (SCI-Expanded, Scopus) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 2 Issue: 3
  • Publication Date: 2006
  • Doi Number: 10.1021/ct060007s
  • Journal Name: JOURNAL OF CHEMICAL THEORY AND COMPUTATION
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.879-884
  • Middle East Technical University Affiliated: Yes

Abstract

N-halamine chemistry has been a research topic of considerable importance in these laboratories for over two decades. N-halamine compounds are useful in preparing biocidal materials. There are three N-Cl moieties available in cyclic N-halamine compounds: imide, amide, and amine. The stabilities toward the release of free halogen have been experimentally shown to decrease in the order amine > amide > imide. In this work, this generalization has been tested theoretically at the level of B3LYP/6-31+G(d) and using the conductor-like polarizable continuum aqueous solvation model with UAKS cavities. Excellent accord was observed between theory and experiment. It was also found that the imide and amide N-halamine stabilities on hydantoin rings could be reversed with substitution patterns at the 5 position.