C-H center dot center dot center dot O hydrogen bonding in 4-phenyl-benzaldehyde: A comprehensive crystallographic, spectroscopic and computational study

authors	Vaz, PD; Nolasco, M; Fonseca, N; Amado, AM; da Costa, AMA; Felix, V; Drew, MGB; Goodfellow, BJ; Ribeiro-Claro, PJA
nationality	International
journal	PHYSICAL CHEMISTRY CHEMICAL PHYSICS
keywords	AB-INITIO CALCULATIONS; VIBRATIONAL SPECTROSCOPY; BONDED DIMERS; NMR; BIPHENYL; DERIVATIVES; BEHAVIOR; BARRIER; FIELD
abstract	The crystal structure of 4-phenyl-benzaldehyde reveals the presence of a dimer linked by the C=O and C( 9)-H groups of adjacent molecules. In the liquid phase, the presence of C-(HO)-O-... bonded forms is revealed by both vibrational and NMR spectroscopy. A Delta H value of - 8.2 +/- 0.5 kJ mol(-1) for the dimerisation equilibrium is established from the temperature-dependent intensities of the bands assigned to the carbonyl-stretching modes. The NMR data suggest the preferential engagement of the C(2,6)-H and C(10/12)/C(11)-H groups as hydrogen bond donors, instead of the C(9)-H group. While ab initio calculations for the isolated dimers are unable to corroborate these NMR results, the radial distribution functions obtained from molecular dynamics simulations show a preference for C(2,6)-H and C(10/12)/C(11)-(HO)-O-... contacts relative to the C(9)-(HO)-O-... ones.
publisher	ROYAL SOC CHEMISTRY
issn	1463-9076
year published	2005
volume	7
issue	16
beginning page	3027
ending page	3034
digital object identifier (doi)	10.1039/b506834g
web of science category	Chemistry, Physical; Physics, Atomic, Molecular & Chemical
subject category	Chemistry; Physics
unique article identifier	WOS:000230931200006