This work studies the underlying nature of H-bonds (HBs) of different types and strengths and tries to predict binding energies (BEs) based on the properties derived from wave function analysis. A total of 42 HB complexes constructed from 28 neutral and 14 charged monomers were considered. This set was designed to sample a wide range of HB strengths to obtain a complete view about HBs. BEs were derived with the accurate coupled cluster singles and doubles with perturbative triples correction (CCSD(T))(T) method and the physical components of the BE were investigated by symmetry-adapted perturbation theory (SAPT). Quantum theory of atoms-in-molecules (QTAIM) descriptors and other HB indices were calculated based on high-quality density functional theory wave functions. We propose a new and rigorous classification of H-bonds (HBs) based on the SAPT decomposition. Neutral complexes are either classified as "very weak" HBs with a BE ≥ -2.5 kcal/mol that are mainly dominated by both dispersion and electrostatic interactions or as "weak-to-medium" HBs with a BE varying between -2.5 and -14.0 kcal/mol that are only dominated by electrostatic interactions. On the other hand, charged complexes are divided into "medium" HBs with a BE in the range of -11.0 to -15.0 kcal/mol, which are mainly dominated by electrostatic interactions, or into "strong" HBs whose BE is more negative than -15.0 kcal/mol, which are mainly dominated by electrostatic together with induction interactions. Among various explored correlations between BEs and wave function-based HB descriptors, a fairly satisfactory correlation was found for the electron density at the bond critical point (BCP; ρBCP ) of HBs. The fitted equation for neutral complexes is BE/kcal/mol = - 223.08 × ρBCP /a. u. + 0.7423 with a mean absolute percentage error (MAPE) of 14.7%, while that for charged complexes is BE/kcal/mol = - 332.34 × ρBCP /a. u. - 1.0661 with a MAPE of 10.0%. In practice, these equations may be used for a quick estimation of HB BEs, for example, for intramolecular HBs or large HB networks in biomolecules. © 2019 Wiley Periodicals, Inc.

Beijing Kein Research Center for Natural Sciences Beijing 100022 People's Republic of China

Chemistry Department Shahrood Branch Islamic Azad University Shahrood Iran

Institute of Biophysics of the Czech Academy of Sciences Královopolská 135 612 65 Brno Czech Republic

Materials Science and Metallurgy Department Technology and Processing of New Materials Research Center Neyshabur Branch Islamic Azad University Neyshabur Iran

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