The nature of hydrogen bonding was compared in;neutral complexes and negatively charged complexes consisting of either the HF molecule or the halide anion (fluoride and chloride) and the C-H bond in the methane molecule with a varying degree of fluorination, (such as CH(4), CH(2)F(2), and CHF(3)). Both linear (C(3v) symmetry) and nonlinear (C(2v) symmetry) hydrogen-bonded complexes were studied. Symmetry-adapted perturbation theory was used to decompose interaction energies into fundamental components such as Coulomb, repulsion, induction and dispersion to analyze the interplay among these forces in stabilizing hydrogen bonding. In the linear charged complexes, both Coulomb attraction and induction significantly contributed to the stabilization of hydrogen bonding. In the nonlinear charged complexes, mainly Coulomb attraction contributed to the HB complex stabilization, with the inductive forces playing a less important role. Contrary to the neutral complexes, dispersion forces played only a marginal role in the charged complexes. Interplay between the fundamental forces was also investigated in the ion pairs of the imidazolium-based ionic liquid, [C(2)min]Cl, that were categorized as either (1) typical ion ion interaction, with the anion interacting from above or below the imidazolium plane; or (2) hydrogen bonding interaction, with the anion interacting with the C2-H bond of the imidazolium cation. Both types Of interactions were found to induce similar charge transfers, and the analysis of the energetic components revealed only a slight difference in the ion pairs studied: (1) both. interactions were electrostatically driven, between 86 and 88 of the overall attractive energy, with the electrostatic component. being slightly lower in the hydrogen bonded ion pairs by similar to 8 kJ mol(-1); and (2) dispersion forces were found to be stronger in the typical ion ion interactions by similar to 15 kJ mol(-1) and could be possible only due to the fact that the anion was able to move closer to the cation with no steric hindrance. From the experimental point of view, a vibrational red shift is expected in the hydrogen bonded complexes of imidazolium-based ionic liquids, whereas the ion ion interactions are more likely to produce a slight blue shift.