Importance of secondary electrostatic interactions in hydrogen-bonding complexes: an investigation using the self-consistent charge and configuration method for subsystems

We have examined the energy components of hydrogen-bonding interactions by using self-consistent charge and configuration method for subsystems (SCCCMS) and charge sensitivity parameters. Our procedure indicated that the main source of the stabilization for hydrogen-bonding association was the electrostatic contribution. The secondary electrostatic and polarization interactions due to polar functional groups located closely to the hydrogen-bonding sites were shown to significantly alter the magnitude of hydrogen-bonding stabilization. This finding supports Jorgensen and co-workers' interpretation toward the hydrogen-bonding energies [e.g., W.L. Jorgensen, D.L. Severance, J. Am. Chem. Sec. 113 (1991) 209]. (C) 2000 Published by Elsevier Science B.V. All rights reserved.