Measurement of Electric Fields Experienced by Urea Guest Molecules in the 18-Crown-6/Urea (1:5) Host-Guest Complex: An Experimental Reference Point for Electric-Field-Assisted Catalysis

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DOI

  • Ming W. Shi, University of Western Australia
  • ,
  • Sajesh P. Thomas
  • Venkatesha R. Hathwar
  • Alison J. Edwards, Australian Nuclear Science and Technology Organisation
  • ,
  • Ross O. Piltz, Australian Nuclear Science and Technology Organisation
  • ,
  • Dylan Jayatilaka, University of Western Australia
  • ,
  • George A. Koutsantonis, University of Western Australia
  • ,
  • Jacob Overgaard
  • Eiji Nishibori, University of Tsukuba
  • ,
  • Bo B. Iversen
  • Mark A. Spackman, University of Western Australia

High-resolution synchrotron and neutron single-crystal diffraction data of 18-crown-6/(pentakis)urea measured at 30 K are combined, with the aim of better appreciating the electrostatics associated with intermolecular interactions in condensed matter. With two 18-crown-6 molecules and five different urea molecules in the crystal, this represents the most ambitious combined X-ray/synchrotron and neutron experimental charge density analysis to date on a cocrystal or host-guest system incorporating such a large number of unique molecules. The dipole moments of the five urea guest molecules in the crystal are enhanced considerably compared to values determined for isolated molecules, and 2D maps of the electrostatic potential and electric field show clearly how the urea molecules are oriented with dipole moments aligned along the electric field exerted by their molecular neighbors. Experimental electric fields in the range of 10-19 GV m -1 , obtained for the five different urea environments, corroborate independent measurements of electric fields in the active sites of enzymes and provide an important experimental reference point for recent discussions focused on electric-field-assisted catalysis.

Original languageEnglish
JournalJournal of the American Chemical Society
Volume141
Issue9
Pages (from-to)3965-3976
Number of pages12
ISSN0002-7863
DOIs
Publication statusPublished - 2019

    Research areas

  • ACTIVE-SITE, CHARGE-DENSITY ANALYSIS, CROWN-ETHERS, DIPOLE-MOMENT ENHANCEMENT, GRAPH-SET ANALYSIS, HYDROGEN-BOND PATTERNS, INTERMOLECULAR INTERACTIONS, NEUTRON-DIFFRACTION, ROOM-TEMPERATURE, X-RAY-DIFFRACTION

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