The existence of a cooperative effect between hydrogen, lithium and halogen bonding within intermolecular interactions has been proven [1]. The study of systems that can enhance this effect could be treated as a matter of interest. Pyridine derivatives that can be considered as prototypes of aromatic systems, due to their importance role in all fields of modern chemistry, have devoted a large number of studies to themselves. However, a little consideration has been paid to the effect of these systems or their derivatives on the cooperativity between halogen and either hydrogen or lithium bonding [2]. In the present study, the effects of the substituents on the binding energies of the X-Py· ··ClCN···LiOH triads (X = H, F, OH, NO2, CH3, NH2, CN and Cl; Py = pyridine) and the cooperative effects of the halogen and lithium bonding, simultaneously, have been investigated.
