The effect of substitution on the intramolecular hydrogen bonding in 3-hydroxy-propenethial

The intramolecular hydrogen bond strength of 3-hydroxy-propenethial (HPT) as well as the fluoro, chloro, bromo, and methyl derivatives were investigated at the B3LYP/6-311++G** level of theory. Solvent-based calculations (in water) for HPT and derivatives were also carried out. The nature of the intramolecular hydrogen bond existing within the molecular under investigation has been studied by means of the Bader theory of atoms in molecules (AIM) that is based upon the use topological properties in terms of the electron density. (C) 2008 Wiley Periodicals, Inc.