title: Mechanism of formation of biocidal imidazolidin-4-one derivatives: an Ab initio density-functional theory study.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Auburn University, Alabama 36849, USA.
authors.forename: Akin
authors.initials: A
authors.lastname: Akdag
authors.forename: Michael L
authors.initials: ML
authors.lastname: McKee
authors.forename: S D
authors.initials: SD
authors.lastname: Worley
mesh_terms: D018360:Crystallography, X-Ray; D004202:Disinfectants / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D048289:Imidazolidines / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D013816:Thermodynamics
chemical_list: C108762:2,2,5,5-tetramethyl-4-imidazolidinone; D004202:Disinfectants; D007093:Imidazoles; D048289:Imidazolidines