A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structur...

Autores
Gil, Diego M.; Salomón, Fernando F.; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Pérez, Hiram; Ben Altabef, Aida
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Schiff base of the title has been synthesized and its crystal structure determined by single-crystal X-ray diffraction. The compound was characterized by IR, Raman, 1H NMR, 13C NMR and electronic absorption spectra. DFT calculations provide the quantumchemical basis for the observed molecular conformation. A study of intermolecular interactions of the title compound is comparedwith seven other closely related structures and reveals that molecules in most of the compounds are linked by a cooperative effect of strong and weak hydrogen bonds, C\\H…π, and π…π stacking interactions, and also lp…π contacts. Lattice energy calculations indicate that the dispersion component is the major contribution, with the coulombic term playing a significant role in the total energy. Interaction energies for molecular pairs involving N\\H···N bonds indicate a dominant contribution to packing stabilization coming from coulomb component. Hirshfeld surfaces and 2D–fingerprint plots allowed us to visualize different intermolecular contacts and its relative contributions to total surface in each compound. The analysis of electrostatic potential (ESP) maps correlates well with the computed energies providing evidences on the dominant electrostatic nature of N\\H···N and N\\H···O interactions.
Instituto de Física La Plata
Materia
Física
Sulfa drugs
Schiff bases
Intermolecular interactions
Hirshfeld surfaces
Crystal structure
IR and Raman spectroscopy
Electronic spectra
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/117228
Acceder
id SEDICI_4473a5ca6cd09d6999dc1037492c7fac
oai_identifier_str oai:sedici.unlp.edu.ar:10915/117228
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysisGil, Diego M.Salomón, Fernando F.Echeverría, Gustavo AlbertoPiro, Oscar EnriquePérez, HiramBen Altabef, AidaFísicaSulfa drugsSchiff basesIntermolecular interactionsHirshfeld surfacesCrystal structureIR and Raman spectroscopyElectronic spectraThe Schiff base of the title has been synthesized and its crystal structure determined by single-crystal X-ray diffraction. The compound was characterized by IR, Raman, 1H NMR, 13C NMR and electronic absorption spectra. DFT calculations provide the quantumchemical basis for the observed molecular conformation. A study of intermolecular interactions of the title compound is comparedwith seven other closely related structures and reveals that molecules in most of the compounds are linked by a cooperative effect of strong and weak hydrogen bonds, C\\H…π, and π…π stacking interactions, and also lp…π contacts. Lattice energy calculations indicate that the dispersion component is the major contribution, with the coulombic term playing a significant role in the total energy. Interaction energies for molecular pairs involving N\\H···N bonds indicate a dominant contribution to packing stabilization coming from coulomb component. Hirshfeld surfaces and 2D–fingerprint plots allowed us to visualize different intermolecular contacts and its relative contributions to total surface in each compound. The analysis of electrostatic potential (ESP) maps correlates well with the computed energies providing evidences on the dominant electrostatic nature of N\\H···N and N\\H···O interactions.Instituto de Física La Plata2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf286-297http://sedici.unlp.edu.ar/handle/10915/117228enginfo:eu-repo/semantics/altIdentifier/issn/1386-1425info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2017.05.066info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-10-22T17:08:26Zoai:sedici.unlp.edu.ar:10915/117228Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-10-22 17:08:27.238SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
title A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
spellingShingle A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
Gil, Diego M.
Física
Sulfa drugs
Schiff bases
Intermolecular interactions
Hirshfeld surfaces
Crystal structure
IR and Raman spectroscopy
Electronic spectra
title_short A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
title_full A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
title_fullStr A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
title_full_unstemmed A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
title_sort A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl) benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis
dc.creator.none.fl_str_mv Gil, Diego M.
Salomón, Fernando F.
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Pérez, Hiram
Ben Altabef, Aida
author Gil, Diego M.
author_facet Gil, Diego M.
Salomón, Fernando F.
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Pérez, Hiram
Ben Altabef, Aida
author_role author
author2 Salomón, Fernando F.
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Pérez, Hiram
Ben Altabef, Aida
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Física
Sulfa drugs
Schiff bases
Intermolecular interactions
Hirshfeld surfaces
Crystal structure
IR and Raman spectroscopy
Electronic spectra
topic Física
Sulfa drugs
Schiff bases
Intermolecular interactions
Hirshfeld surfaces
Crystal structure
IR and Raman spectroscopy
Electronic spectra
dc.description.none.fl_txt_mv The Schiff base of the title has been synthesized and its crystal structure determined by single-crystal X-ray diffraction. The compound was characterized by IR, Raman, 1H NMR, 13C NMR and electronic absorption spectra. DFT calculations provide the quantumchemical basis for the observed molecular conformation. A study of intermolecular interactions of the title compound is comparedwith seven other closely related structures and reveals that molecules in most of the compounds are linked by a cooperative effect of strong and weak hydrogen bonds, C\\H…π, and π…π stacking interactions, and also lp…π contacts. Lattice energy calculations indicate that the dispersion component is the major contribution, with the coulombic term playing a significant role in the total energy. Interaction energies for molecular pairs involving N\\H···N bonds indicate a dominant contribution to packing stabilization coming from coulomb component. Hirshfeld surfaces and 2D–fingerprint plots allowed us to visualize different intermolecular contacts and its relative contributions to total surface in each compound. The analysis of electrostatic potential (ESP) maps correlates well with the computed energies providing evidences on the dominant electrostatic nature of N\\H···N and N\\H···O interactions.
Instituto de Física La Plata
description The Schiff base of the title has been synthesized and its crystal structure determined by single-crystal X-ray diffraction. The compound was characterized by IR, Raman, 1H NMR, 13C NMR and electronic absorption spectra. DFT calculations provide the quantumchemical basis for the observed molecular conformation. A study of intermolecular interactions of the title compound is comparedwith seven other closely related structures and reveals that molecules in most of the compounds are linked by a cooperative effect of strong and weak hydrogen bonds, C\\H…π, and π…π stacking interactions, and also lp…π contacts. Lattice energy calculations indicate that the dispersion component is the major contribution, with the coulombic term playing a significant role in the total energy. Interaction energies for molecular pairs involving N\\H···N bonds indicate a dominant contribution to packing stabilization coming from coulomb component. Hirshfeld surfaces and 2D–fingerprint plots allowed us to visualize different intermolecular contacts and its relative contributions to total surface in each compound. The analysis of electrostatic potential (ESP) maps correlates well with the computed energies providing evidences on the dominant electrostatic nature of N\\H···N and N\\H···O interactions.
publishDate 2017
dc.date.none.fl_str_mv 2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/117228
url http://sedici.unlp.edu.ar/handle/10915/117228
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1386-1425
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2017.05.066
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
286-297
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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