Simultaneous interactions of pyridine with substituted benzene ring and H–F in X-ben⊥pyr···H–F complexes: a cooperative study

Abstract

The cooperative effects between T-shape stacking and hydrogen bond interactions in X-ben⊥pyr···H–F complexes were investigated in this work. The results indicate that the electron-withdrawing/donating substituents decrease/increase the magnitude of the binding energies compared to the unsubstituted X-ben⊥pyr···H–F (X = H) complex. The cooperative effects have been studied while using the atoms in molecules (AIM) and natural bond orbital (NBO) methods, allowing us to evaluate the interplay between T-shape stacking and hydrogen bond interactions. There are good relationships among binding energies, Hammett constants, geometrical parameters, and the results of AIM and NBO analysis in X-ben⊥pyr···H–F complexes.