Crystal Engineering through Halogen Bonding: Complexes of Nitrogen Heterocycles with Organic Iodides

Rosa Bailey Walsh, Clifford W. Padgett, Pierangelo Metrangolo, Giuseppe Resnati, T. W. Hanks, William T. Pennington

Research output: Contribution to journalArticlepeer-review

339 Scopus citations

Abstract

X-ray analysis has revealed that 4,4′-bipyridine, 1,2-bis(4-pyridyl)ethylene, and hexamethylenetetramine form donor - acceptor complexes with 1,4-diiodobenzene, 1,4-diiodotetrafluorobenzene, and tetraiodoethylene in which the N⋯I distance is longer than that for the corresponding I2 complexes. As opposed to the corresponding I2 complexes that are molecular adducts, these complexes have extended structures and longer N⋯I distances. Steric and electronic effects influence the strength of the N⋯I interaction and the crystal packing. An additional complex of 1,2-bis(4-pyridyl)ethane and 1,4-dibromotetrafluorobenzene has also been investigated for comparison of N⋯I and N⋯Br interactions.

Original languageEnglish
Pages (from-to)165-175
Number of pages11
JournalCrystal Growth and Design
Volume1
Issue number2
DOIs
StatePublished - Mar 2001

Scopus Subject Areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics

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