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The Ability of a Tetrel Bond to Transition a Neutral Amino Acid into a Zwitterion

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  • Additional Information
    • Contributors:
      Elsevier BV
    • Publication Information:
      Hosted by Utah State University Libraries
    • Publication Date:
      2019
    • Collection:
      Utah State University: DigitalCommons@USU
    • Abstract:
      The interaction between glycine and F2CO/F2SiO occurs through the formation of a π-tetrel bond between the C/Si atom and a carboxyl O atom. The interaction energy is some 20 kJ/mol for the C···O tetrel bond, but exceeds 300 kJ/mol for Si···O. As part of the latter complexation process, the proton engaged in the intramolecular OH··N H-bond is transferred across to the N, forming a zwitterion. This Si···O tetrel bond is more effective at inducing this proton transfer than is placement of the glycine in an aqueous medium, complexation with an anionic BH4-, or adding an electron to the glycine.
    • File Description:
      application/pdf
    • Relation:
      https://digitalcommons.usu.edu/chem_facpub/880; https://digitalcommons.usu.edu/context/chem_facpub/article/1880/viewcontent/auto_convert.pdf
    • Accession Number:
      10.1016/j.cplett.2019.07.012
    • Online Access:
      https://digitalcommons.usu.edu/chem_facpub/880
      https://doi.org/10.1016/j.cplett.2019.07.012
      https://digitalcommons.usu.edu/context/chem_facpub/article/1880/viewcontent/auto_convert.pdf
    • Rights:
      Copyright for this work is held by the author. Transmission or reproduction of materials protected by copyright beyond that allowed by fair use requires the written permission of the copyright owners. Works not in the public domain cannot be commercially exploited without permission of the copyright owner. Responsibility for any use rests exclusively with the user. For more information contact the Institutional Repository Librarian at digitalcommons@usu.edu. ; http://creativecommons.org/licenses/by-nc-nd/4.0/
    • Accession Number:
      edsbas.76D05281