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Ab initio and Semiempirical Conformational and Configurational Analysis of N-2-(1,4Dioxane)~ Nי-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy)isourea

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The conformational, configurational behavior and the structure of N-2-(l ,4-dioxane)-Nי-(4-methylbenzenesulfonyl)-O-(4methylphenoxy) isourea 1 has been studied using ab initio and semiempirical calculations (AM1 and PM3). The endo-anomeric effect and hydrogen bonds control the population of dioxane ring conformers or anomers but not the configuration interconversion of the imine of imidoyl moiety . Ab initio and AMI and PM3 calculations demonstrate that the dioxane ring adopts a chair conformation, that the imidoyl amino group prefers an axial conformation and that the tosyl and tolyl groups about the C=N bond retain an E configuration. The computational analysis of 1 complements the X-ray findings.

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