The definitive challenge of forming uncommon pseudo‐π···H–F and C···H–F hydrogen bonds on cyclic and cubic nonpolar hydrocarbons

Abstract

AbstractDue to the high symmetry and low polarity of the cyclopropane (C3H6), cyclobutane (C4H8), prismane (C6H6), and cubane (C8H8), it is widely known that these structures unlikely act as proton receptors to form intermolecular interactions with monoprotic acids, such as the hydrogen fluoride. Although the C3H6···HF, C4H8···HF, C6H6···HF, and C8H8···HF are weakly bound complexes, in this current work, all of them were definitively certified on the basis of a theoretical analysis. In according with the structural parameters and spectroscopy modes appraised through the density‐functional theory calculations, the more accentuated perturbations are manifested in the hydrogen fluoride. The new hydrogen bond forms framed as pseudo‐π···H and C···H were unveiled through the calculations of the quantum theory of atoms in molecules and natural bond orbital. In this context, the knowledge about the nature of these hydrogen bonds is necessary, wherein it used the symmetry‐adapted perturbation theory for computing the contributions of the electrostatic, polarization, exchange, dispersion, and charge transfer terms. Lastly, the practical behavior of these hydrocarbons under the condition to form intermolecular interactions was examined by taking into account the solvent effect with calculations of the polarizable continuum model.