C-H...O hydrogen bonding in 4-phenyl-benzaldehyde: a comprehensive crystallographic, spectroscopic and computational study |
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Authors: | Vaz Pedro D Nolasco Mariela Fonseca Nelson Amado Ana M Costa António M Amorim da Félix Vitor Drew Michael G B Goodfellow Brian J Ribeiro-Claro Paulo J A |
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Institution: | CICECO, Departamento de Química, Universidade de Aveiro, P-3810-193 Aveiro, Portugal. |
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Abstract: | The crystal structure of 4-phenyl-benzaldehyde reveals the presence of a dimer linked by the C=O and C9-H groups of adjacent molecules. In the liquid phase, the presence of C-H...O bonded forms is revealed by both vibrational and NMR spectroscopy. A DeltaH 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)-H...O contacts relative to the C(9)-H...O ones. |
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