Organic Chemistry

Dual Chalcogen-Bonding Interaction for Conformational Control of Urea

Authors

  • Takumi Furuta Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Takumi Inoue Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Moe Ota Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Yui Amijima Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Haru Takahashi Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Shohei Hamada Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Yusuke Kobayashi Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University ,
  • Takahiro Sasamori Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba

Abstract

A dual chalcogen-bonding interaction was proposed as a novel means for the conformational control of urea derivatives. The formation of a chalcogen-bonding interaction at both sides of the urea carbonyl group was unambiguously revealed by X-ray diffraction, as well as by natural bond orbital (NBO) analysis via DFT calculations. By virtue of this dual interaction, urea derivatives bearing chalcogen atoms (X = S and Se) were made to adopt a planar structure via the carbonyl oxygen (O) with an X•••O•••X arrangement on the same side of the molecule. Tweezer-shaped urea derivatives were also developed based on conformational control using the dual chalcogen-bonding interaction.

Content

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Supplementary material

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Supporting Information
Experimental procedures, spectroscopic and X-ray data for all new compounds, and computational data