Britton, D.; Cramer, C. J.
Acta Cryst. 2006, C62, o307.
2-Cyanobenzaldehyde, C8H5NO, has an intramolecular O...CN contact involving an O-C distance of 2.797(2) ang and a C-C-N bond angle of 174.5(2) deg, 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 nO1-->π*CN delocalization energy of 6.3 kJ mol-1. Similar results were obtained from density functional calculations on three related molecules. The 2-cyanobenzaldehyde molecules pack in sheets as a consequence of C-H...N and C-H...O hydrogen bonds.
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