Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Attractive Sulfur...π Interaction between Fluorinated Dimethyl Sulfur (FDMS) and Benzene

  • Yan, Shihai (Department of Chemistry, Sungkyunkwan University) ;
  • Lee, Sang-Joo (Center for Computational Biology and Bioinformatics, Korea Institute of Science and Technology Information) ;
  • Kang, Sun-Woo (Department of Chemistry, Sungkyunkwan University) ;
  • Choi, Kwang-Hyun (Department of Chemistry, Sungkyunkwan University) ;
  • Rhee, Soon-Ki (Department of Chemistry, Chonnam National University) ;
  • Lee, Jin-Yong (Department of Chemistry, Sungkyunkwan University)
  • Published : 2007.06.20
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Abstract

The benzene complexes with dimethyl sulfur (DMS) and fluorinated DMS (FDMS) have been investigated using ab initio calculations. The natural bond orbital (NBO) charge population on S atom varies remarkably for different conformations of DMS and FDMS, which determines the possible binding modes for their benzene complexes. The electronegative substituent at the methyl group of DMS causes a significant change in the molecular electrostatic potential around the sulfur atom and changes the interaction mode with aromatic ring. It was found that the sulfur…π interaction mode does not occur in the DMS-benzene complex, while it does in the FDMS-benzene complex. Both B3LYP and MP2 methods provide reliable structures, while the interaction energy obtained by B3LYP is unreliable.

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