Complexes of 4-substituted phenolates with HF and HCN: Energy decomposition and electronic structure analyses of hydrogen bonding

Halina Szatyłowicz , Tadeusz Marek Krygowski , Célia Fonseca Guerra , F. Matthias Bickelhaupt


We have computationally studied para-X-substituted phenols and phenolates (X = NO, NO2, CHO, COMe, COOH, CONH2, Cl, F, H, Me, OMe, and OH) and their hydrogen-bonded complexes with B− and HB (B = F and CN), respectively, at B3LYP/6-311++G** and BLYP-D/QZ4P levels of theory. Our purpose is to explore the structures and stabilities of these complexes. Moreover, to understand the emerging trends, we have analyzed the bonding mechanisms using the natural bond orbital scheme as well as Kohn–Sham molecular orbital (MO) theory in combination with quantitative energy decomposition analyses [energy decomposition analysis (EDA), extended transition state-natural orbitals for chemical valence (ETS-NOCV)]. These quantitative analyses allow for the construction of a simple physical model that explains all computational observations. © 2012 Wiley Periodicals, Inc.
Author Halina Szatyłowicz (FC / DPC)
Halina Szatyłowicz,,
- Department Of Physical Chemistry
, Tadeusz Marek Krygowski
Tadeusz Marek Krygowski,,
, Célia Fonseca Guerra
Célia Fonseca Guerra,,
, F. Matthias Bickelhaupt
F. Matthias Bickelhaupt,,
Journal seriesJournal of Computational Chemistry, ISSN 0192-8651, [1096-987X]
Issue year2013
Publication size in sheets0.5
Keywords in EnglishADF, Hydrogen bond, NBO, phenol, phenolate, substituent effect
ASJC Classification2605 Computational Mathematics; 1600 General Chemistry
Languageen angielski
jcc-34_696-2013.pdf 1.31 MB
Score (nominal)35
Score sourcejournalList
ScoreMinisterial score = 35.0, 31-01-2020, ArticleFromJournal
Ministerial score (2013-2016) = 35.0, 31-01-2020, ArticleFromJournal
Publication indicators Scopus Citations = 6; WoS Citations = 6; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 1.517; WoS Impact Factor: 2013 = 3.601 (2) - 2013=4.72 (5)
Citation count*4 (2015-02-17)
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