In this study, the drastic influence of the boron atom on the acidity of alcohol has been considered. The calculated ΔHacid(320.9–338.1 kcal/mol) and pKarange of boron containing alcohol (-0.1–9.4) indicate that the boronation of alcohol leads to considerable enhancement of its acidity. For instance, we have obtained the ΔHacidvalues 338.1, 335.2 kcal/mol and the pKavalues 4.12, 2.81 for BH2CH2OH , BF2CH2OH alcohols, respectively, which are much smaller than that of CH3OH (with ΔHacid= 374.9 kcal/mol and pKa= 15). The increase in the acidity of boronated alcohol can be related to the stabilization of alkoxy ion due to overlap of unoccupied orbital of boron atom with the electron pairs of negative oxygen. All gas phase computations were performed at MP2/6-311++G(d,p)//(B3LYP/6-31+G(d)) level. The primary results indicate that the presence of boron atom in an alcohol might make it as acidic as nitric acid. The geometry optimization of studied structures was performed with DFT computation and optimized structures were used to carry out natural bond orbital (NBO) analysis. NBO analysis revealed that the increase in the acidity of boron-containing alcohols is due to the charge transfer from the negative oxygen (in deprotonated structure) to the empty orbital of - BH2and - BF2. Quantum theory of atoms in molecules (QTAIM) was also applied to determine the nature of bonds formed in the deprotonated structure.