Ab initio studies of the characteristics of hydrogen bonds involving aromatically bound hydroxyl and amino groups and the effects of aromatic fluorine substitution on these interactions

Abstract

AbstractIn this work, we study the hydrogen bonds (H‐bonds) involving hydroxyl and amino groups bonded to phenyl and pyrimidine rings (as H‐bond donors). These types of interactions play important roles in the recognition of ligands by proteins and are also important in the design of materials. The effects of aromatic fluorine substitutions on aromatic rings are also investigated, and it is found that these substitutions can have large effects on the hydrogen bonding interactions that occur in our model systems, making them substantially stronger. This finding offers a new mechanism for the modification of these types of interactions, potentially opening new paths in the design of novel pharmaceuticals and materials. © 2009 Wiley Periodicals, Inc. Int J Quantum Chem, 2010