title: Nature and strength of C-H···O interactions involving formyl hydrogen atoms: computational and experimental studies of small aldehydes.
abstract: Structural and electronic properties of C-H···O contacts in compounds containing a formyl group are investigated from the perspective of both hydrogen bonding and dipole-dipole interactions, in a systematic and graded approach. The effects of α-substitution and self-association on the nature of the formyl H-atom are studied with the NBO and AIM methodologies. The relative dipole-dipole contributions in formyl C-H···O interactions are obtained for aldehyde dimers. The stabilities and energies of aldehyde clusters (dimer through octamer) have been examined computationally. Such studies have an implication in crystallization mechanisms. Experimental X-ray crystal structures of formaldehyde, acrolein and N-methylformamide have been determined in order to ascertain the role of C-H···O interactions in the crystal packing of formyl compounds.
authors.affiliation: Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India. desiraju@sscu.iisc.ernet.in.
authors.forename: Tejender S
authors.initials: TS
authors.lastname: Thakur
authors.forename: Michael T
authors.initials: MT
authors.lastname: Kirchner
authors.forename: Dieter
authors.initials: D
authors.lastname: Bläser
authors.forename: Roland
authors.initials: R
authors.lastname: Boese
authors.forename: Gautam R
authors.initials: GR
authors.lastname: Desiraju