Doyle Britton, Christopher J. Cramer

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The title compound, C8H5NO, has an intramolecular O⋯CN contact involving an O⋯C distance of 2.797(2) and a C - C - N bond angle of 174.5(2)°, both indicative of a weak nucleophilic attack of the aldehyde O atom on the electrophilic C atom in the nitrile group. Calculations at the B3LYP density functional level using the 6-31G* basis set support this interpretation; natural bond-order analysis indicates an n O1→π delocalization energy of 6.3kJmol-1. Similar results were obtained from density functional calculations on three related molecules. The 2-formylbenzonitrile molecules pack in sheets as a consequence of C - H⋯N and C - H⋯O hydrogen bonds.

Original languageEnglish (US)
Pages (from-to)o307-o309
JournalActa Crystallographica Section C: Crystal Structure Communications
Issue number6
StatePublished - Jun 1 2006


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