The stabilities of N-Cl bonds in biocidal materials

Date

2006-05-01

Author

Akdağ, Akın
McKee, Michael L.
Worley, S. D.

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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.

Subject Keywords

Physical and Theoretical Chemistry, Computer Science Applications

URI

https://hdl.handle.net/11511/57726

Journal

JOURNAL OF CHEMICAL THEORY AND COMPUTATION

DOI

https://doi.org/10.1021/ct060007s

Collections

Department of Chemistry, Article

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Citation Formats

A. Akdağ, M. L. McKee, and S. D. Worley, “The stabilities of N-Cl bonds in biocidal materials,” JOURNAL OF CHEMICAL THEORY AND COMPUTATION, pp. 879–884, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57726.