title: The Stabilities of N-Cl Bonds in Biocidal Materials.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849.
authors.forename: Akin
authors.initials: A
authors.lastname: Akdag
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849.
authors.forename: Serife
authors.initials: S
authors.lastname: Okur
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849.
authors.forename: Michael L
authors.initials: ML
authors.lastname: McKee
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849.
authors.forename: S D
authors.initials: SD
authors.lastname: Worley