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

Date

2006-06-01

Author

Akdağ, Akın
Worley, S. D.

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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.

Subject Keywords

Physical and Theoretical Chemistry

URI

https://hdl.handle.net/11511/57521

Journal

JOURNAL OF PHYSICAL CHEMISTRY A

DOI

https://doi.org/10.1021/jp060879q

Collections

Department of Chemistry, Article

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Citation Formats

A. Akdağ and S. D. Worley, “Mechanism of formation of biocidal imidazolidin-4-one derivatives: An ab initio density-functional theory,” JOURNAL OF PHYSICAL CHEMISTRY A, pp. 7621–7627, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57521.