Hydrogen bonds determine the structures of the ternary heterocyclic complexes C2H4O···2HF, C2H5N···2HF and C2H4S···2HF: density functional theory and topological calculations

A theoretical study of structural, electronic, topological and vibrational parameters of the ternary hydrogen-bonded complexes C 2 H 4 O···2HF, C 2 H 5 N···2HF and C 2 H 4 S···2HF is presented here. Different from binary systems with a single proton donor, the tricomplexes have the property of formi...

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Bibliographic Details
Published in:Journal of molecular modeling 2011-11, Vol.17 (11), p.2847-2862
Main Authors: Oliveira, Boaz G., Araújo, Regiane C. M. U., Carvalho, Antônio B., Ramos, Mozart N.
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Computer Appl. in Life Sciences
Computer Applications in Chemistry
Heterocyclic Compounds - chemistry
Hydrogen Bonding
Models, Molecular
Molecular Medicine
Original Paper
Quantum Theory
Reproducibility of Results
Theoretical and Computational Chemistry
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Summary:A theoretical study of structural, electronic, topological and vibrational parameters of the ternary hydrogen-bonded complexes C 2 H 4 O···2HF, C 2 H 5 N···2HF and C 2 H 4 S···2HF is presented here. Different from binary systems with a single proton donor, the tricomplexes have the property of forming multiple hydrogen bonds, which are analyzed from a structural and vibrational point of view, but verified only by means of the quantum theory of atoms in molecules (QTAIM). As traditionally done in the hydrogen bond theory, the charge transfer between proton donors and acceptors was computed using the CHELPG calculations, which also revealed agreement with dipole moment variation and a cooperative effect on the tricomplexes. Furthermore, redshift events on proton donor bonds were satisfactorily identified, although, in this case, an absence of experimental data led to the use of a theoretical argument to interpret these spectroscopic shifts. It was therefore the use of the QTAIM parameters that enabled all intermolecular vibrational modes to be validated. The most stable tricomplex in terms of energy was identified via the strength of the hydrogen bonds, which were modeled as directional and bifurcated.
ISSN:1610-2940
0948-5023
DOI:10.1007/s00894-011-0969-8