Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds

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Ab initio calculations are used to analyze the effect of C-H···O hydrogen bonding interactions on the C-H bond length. Methane derivatives, CH4-nXn (where n = 1, 2, 3 for X = F and n = 1 for X = NO2) are taken as proton donors and H2O as acceptor. The topological properties of electronic charge dens...

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Autores principales: Sosa, G.L., Peruchena, N.M., Contreras, R.H., Castro, E.A.
Formato: JOUR
Materias:
Bader's AIM theory
Charge transfer
Hydrogen bonding
Intermolecular interactions
NBO
alkane derivative
hydrogen
methane derivative
unclassified drug
article
binding affinity
energy transfer
hydrogen bond
molecular interaction
proton transport
reaction analysis
vibration
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01661280_v577_n2-3_p219_Sosa
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_01661280_v577_n2-3_p219_Sosa
record_format dspace
spelling todo:paper_01661280_v577_n2-3_p219_Sosa2023-10-03T15:03:29Z Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds Sosa, G.L. Peruchena, N.M. Contreras, R.H. Castro, E.A. Bader's AIM theory Charge transfer Hydrogen bonding Intermolecular interactions NBO alkane derivative hydrogen methane derivative unclassified drug article binding affinity energy transfer hydrogen bond molecular interaction proton transport reaction analysis vibration Ab initio calculations are used to analyze the effect of C-H···O hydrogen bonding interactions on the C-H bond length. Methane derivatives, CH4-nXn (where n = 1, 2, 3 for X = F and n = 1 for X = NO2) are taken as proton donors and H2O as acceptor. The topological properties of electronic charge density are analyzed employing the Bader's Atoms In Molecules (AIM) theory. A good correlation between the structural parameters and the properties of charge density is found. Then, using the Natural Bond Orbitals (NBO) approach, the effects of charge transfer interactions on the behavior of the C-H bond are investigated. It is found that the competitive effects between intermolecular no → σ(C-H)* and intramolecular nF → σ(C-H)* of charge transfer interactions in the CH4-nFn/H2O systems causes a decrease of the σ(C-H)* antibond occupation number, and concomitantly, a contraction of the corresponding C-H bond. In the NO2CH3/H2O system, the only charge transfer interaction, the no → σ(C-H)* intermolecular interaction cause a increase of the σ(C-H)* antibond occupation number which entails a slight lengthening of the corresponding C-H bond. © 2002 Elsevier Science B.V. All rights reserved. Fil:Contreras, R.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01661280_v577_n2-3_p219_Sosa
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Bader's AIM theory
Charge transfer
Hydrogen bonding
Intermolecular interactions
NBO
alkane derivative
hydrogen
methane derivative
unclassified drug
article
binding affinity
energy transfer
hydrogen bond
molecular interaction
proton transport
reaction analysis
vibration
spellingShingle Bader's AIM theory
Charge transfer
Hydrogen bonding
Intermolecular interactions
NBO
alkane derivative
hydrogen
methane derivative
unclassified drug
article
binding affinity
energy transfer
hydrogen bond
molecular interaction
proton transport
reaction analysis
vibration
Sosa, G.L.
Peruchena, N.M.
Contreras, R.H.
Castro, E.A.
Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds
topic_facet Bader's AIM theory
Charge transfer
Hydrogen bonding
Intermolecular interactions
NBO
alkane derivative
hydrogen
methane derivative
unclassified drug
article
binding affinity
energy transfer
hydrogen bond
molecular interaction
proton transport
reaction analysis
vibration
description Ab initio calculations are used to analyze the effect of C-H···O hydrogen bonding interactions on the C-H bond length. Methane derivatives, CH4-nXn (where n = 1, 2, 3 for X = F and n = 1 for X = NO2) are taken as proton donors and H2O as acceptor. The topological properties of electronic charge density are analyzed employing the Bader's Atoms In Molecules (AIM) theory. A good correlation between the structural parameters and the properties of charge density is found. Then, using the Natural Bond Orbitals (NBO) approach, the effects of charge transfer interactions on the behavior of the C-H bond are investigated. It is found that the competitive effects between intermolecular no → σ(C-H)* and intramolecular nF → σ(C-H)* of charge transfer interactions in the CH4-nFn/H2O systems causes a decrease of the σ(C-H)* antibond occupation number, and concomitantly, a contraction of the corresponding C-H bond. In the NO2CH3/H2O system, the only charge transfer interaction, the no → σ(C-H)* intermolecular interaction cause a increase of the σ(C-H)* antibond occupation number which entails a slight lengthening of the corresponding C-H bond. © 2002 Elsevier Science B.V. All rights reserved.
format JOUR
author Sosa, G.L.
Peruchena, N.M.
Contreras, R.H.
Castro, E.A.
author_facet Sosa, G.L.
Peruchena, N.M.
Contreras, R.H.
Castro, E.A.
author_sort Sosa, G.L.
title Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds
title_short Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds
title_full Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds
title_fullStr Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds
title_full_unstemmed Topological and NBO analysis of hydrogen bonding interactions involving C-H···O bonds
title_sort topological and nbo analysis of hydrogen bonding interactions involving c-h···o bonds
url http://hdl.handle.net/20.500.12110/paper_01661280_v577_n2-3_p219_Sosa
work_keys_str_mv AT sosagl topologicalandnboanalysisofhydrogenbondinginteractionsinvolvingchobonds
AT peruchenanm topologicalandnboanalysisofhydrogenbondinginteractionsinvolvingchobonds
AT contrerasrh topologicalandnboanalysisofhydrogenbondinginteractionsinvolvingchobonds
AT castroea topologicalandnboanalysisofhydrogenbondinginteractionsinvolvingchobonds
_version_ 1807321856520224768

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