How to Model Inter- and Intramolecular Hydrogen Bond Strengths with Quantum Chemistry

被引：7

作者：

Bauer, Christoph A. ^{[1
,2
]}

机构：

[1] Univ Bergen, Dept Chem, N-5007 Bergen, Norway

[2] Univ Bergen, Computat Biol Unit, N-5007 Bergen, Norway

来源：

JOURNAL OF CHEMICAL INFORMATION AND MODELING | 2019年 / 59卷 / 09期

关键词：

MOLECULAR-FORCE FIELD; DENSITY-FUNCTIONAL THEORY; FREE-ENERGY; CONFORMATIONAL ENERGIES; VIBRATIONAL FREQUENCIES; TORSIONAL FREQUENCIES; DESIGN; COMPLEXES; ACCURATE; BASICITY;

D O I：

10.1021/acs.jcim.9b00132

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

This article presents the computation of both inter- and intramolecular hydrogen bond strengths from first-principles. Quantum chemical calculations conducted at the dispersion-corrected density functional theory level including free energy and solvation contributions are conducted for (i) one-to-one hydrogen-bonded complexes of alcohols to N-methyl pyrrolidinone measured by an infrared spectroscopy method and (ii) a set of experimental intramolecular hydrogen bond-forming phenol and pyrrole compounds, with intramolecular hydrogen bond strengths derived from a nuclear magnetic resonance method. The computed complexation free energies in solution show a correlation to experiment of R-2 = 0.74 with a root mean square error of 4.85 kJ mol(-1). The intramolecular hydrogen bonding free energies in solution show a correlation of R-2 = 0.79 with a root mean square error of 5.51 kJ mol(-1). The results of this study can be used as a guide on how to build reliable quantum chemical databases for computed hydrogen bonding strengths.

引用

页码：3735 / 3743

页数：9

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