2-Formylbenzonitrile

Abstract

The title compound, C8H5NO, has an intramolecular O...CN contact involving an O...C distance of 2.797 (2) angstroms and a C-C-N bond angle of 174.5 (2) degrees, 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) --> pi(CN)* delocalization energy of 6.3 kJ mol(-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.