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Abstract) Theoretical calculations were performed to investigate the interplay between sigma holes, anion-HC and cation-π interactions in the complexes of dibromo [2-2] paracyclophane (DBr[2-2]PCP) with alkali (Li+, Na+, K+ ), alkaline earth metal cations (Be++, Mg++, Ca++) and halogen anions (F-, Cl- and Br-) using the wavefunction (MP2) and density functional theory (M06-2X and B3LYP) methods with the 6-311++G(d, p) basis set. The study reveals that DBr[2-2]PCP behaves as amphoteric molecule with a predominance of basic character. It
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