Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Density Functional Theory Demonstration of Anomeric Effect and Structure: Conformational and Configurational Analysis of N-2-(1,4-Dioxane)-N'-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy) Isourea

  • Dabbagh, Hossein A. (Department of Chemistry, Isfahan University of Technology) ;
  • Najafi Chermahini, Ali Reza (Department of Chemistry, Isfahan University of Technology) ;
  • Modarresi-Alam, Ali Reza (Department of Chemistry, Sistan & Baluchestan University)
  • Published : 2005.08.20
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Abstract

The conformational, configurtational behavior and the structure of N-2-(1,4-Dioxane)-N'-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy) isourea 1 has been studied using DFT method. Calculations predict the imidoyl amino group of the dioxane ring prefers axial conformation and that the tosyl and tolyl groups about the C=N bond retain E configuration. The anomeric effect controls the population of dioxane ring conformers, and anomers. Intramolecular hydrogen bonds contribute to the stability of E isomers. The computational analysis of 1 complements the X-ray findings.

Keywords

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