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.

中文翻译：

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杀微生物的咪唑烷基-4-酮衍生物的形成机理：从头算密度函数理论研究。

在过去的20多年中，N-卤胺化学一直是这些实验室中相当重要的研究课题，因为N-卤胺化合物在制备杀菌材料中非常有用。为了理解这些化合物的用途，应该解决环状N-卤胺化合物的卤化的稳定性和机理。在该理论研究中，重要的前体杀生物化合物2,2,5,5-四甲基咪唑啉丁-4-酮（TMIO）被视为模型。理论上在B3LYP / 6-311 + G（2d，p）的水平上研究了单卤代的热力学和动力学产物以及TMIO和琥珀酰亚胺的互变异构。使用具有UAKS腔的CPCM溶剂化模型，包括了溶剂化作用（水和氯仿）。已经提出了几种氯从TMIO环的3-位（运动产物）迁移至1-位（热力学产物）的机理。结果与实验NMR数据一致。