Molecular geometry as a source of chemical information. Part 2—An attempt to estimate the H-bond strength: the case of p-nitrophenol complexes with bases


  • Dedicated to our friend and teacher, Professor Andrzej Górski.


B3LYP/6–311+G** optimizations were carried out for p-nitrophenol interacting with the flouride with the only constraints for O…F distance in the range 4.0–2.601 Å (for 19 computational data points) with an assumption of planarity of the system and linearity of OH…F. The monotonic dependences of interaction energies on C—O bond lengths led us to propose the C—O bond length as an approximate parameter to measure the H-bond strength. Experimental geometries showed that the C—O bond length is very sensitive, and also that it is the most variable structural parameter in these complexes. Copyright © 2004 John Wiley & Sons, Ltd.