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
  ciceco authors
  impact metrics
journal analysis (jcr 2017):
journal impact factor 3.906
5 year journal impact factor 4.224
category normalized journal impact factor percentile 73.037
dimensions (citation analysis):
altmetrics (social interaction):



 


Sponsors

1suponsers_list_ciceco.jpg