The frequency shifts of donor stretching vibration in X-H···Y (X = C, N, O; Y = N, O) hydrogen-bonded complexes of phenylacetylene, indole, and phenol are linearly correlated with the electrostatic component of the interaction energy. This linear correlation suggests that the electrostatic component, which is the first-order perturbative correction to the stabilization energy, is essentially localized on the X-H group. The linear correlation suggests that the electrostatic tuning rate, which is a measure of the X-H oscillator to undergo shifts upon hydrogen bonding per unit increase in the electrostatic component of the stabilization energy, was found to be in the order of O-H > N-H > C-H. Interestingly, for each of the donor groups, viz., C-H, N-H, and O-H, the vibrational frequency shifts were inversely correlated to the dipole moment of the acceptor separately, which is counterintuitive vis-à-vis the electrostatic component. This implies that extrapolation to zero dipole moment of the acceptor will yield very large shifts in the hydrogen-bonded X-H stretching frequencies. The trends in the variation of the dispersion and exchange-repulsion components and the total interaction energy vis-à-vis frequency shifts of donor stretching vibration are similar for hydrogen-bonded complexes of phenylacetylene, indole, and phenol. Furthermore, it was observed that the vibrational frequency shifts of all of the complexes are linearly correlated with the charge transfer from the filled orbital of the hydrogen acceptor to the vacant antibonding (σ*) orbital of the X-H donor group on the basis of natural bonding orbital calculations.