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Molecular pair analysis: C-H...F interactions in the crystal structure of fluorobenzene? And related matters.
Journal article

Molecular pair analysis: C-H...F interactions in the crystal structure of fluorobenzene? And related matters.

  • Dunitz JD Organic Chemistry Laboratory, ETH-Zurich, 8093 Zurich, Switzerland. dunitz@org.chem.ethz.ch
  • Schweizer WB
  • 2006-07-25
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2006
English The crystal structure of fluorobenzene is compared with isomorphous crystal structures of molecules of roughly similar shape. The lowest-energy fluorobenzene dimers are identified by theoretical calculations. Molecular pair analysis of the crystal structure of fluorobenzene and of an isomorphous virtual low-energy polymorph of benzene suggests that the important intermolecular interactions in the two structures are closely similar. In particular, the intermolecular C-H...F interactions in the fluorobenzene crystal have approximately the same structure-directing ability and influence on the intermolecular energy as the corresponding C-H...H interactions in benzene. Molecular pair analysis of the isomorphous crystal structures of benzonitrile, alloxan, and cyclopentene-1,2,3-trione indicates that essentially the same crystal structure can be adopted with quite different patterns of pair energies and atom-atom interactions. The question as to whether the packing radius of organic fluorine is larger or smaller than that of hydrogen, is addressed, but not answered.
Language
  • English
Open access status
closed
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Persistent URL
https://folia.unifr.ch/global/documents/233843
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