Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Autores
Saeed, Aamer; Ashraf, Saba; White, Jonathan M.; Soria, Delia Beatriz; Franca, Carlos Alberto; Erben, Mauricio Federico
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular NA...O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular hydrogen-bonding interactions involving the acylthioureamoiety. Compound 2 is further stabilized by p-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV?Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.
Fil: Saeed, Aamer. Quaid-i-Azam University; Pakistán
Fil: Ashraf, Saba. Quaid-i-Azam University; Pakistán
Fil: White, Jonathan M.. University of Melbourne; Australia
Fil: Soria, Delia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Franca, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
Vibrational Spectroscopy
Quantum Chemical Calculations
X-Ray Crystal Structure
Thiourea
Thermogravimetry
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/48256
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/48256
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculationsSaeed, AamerAshraf, SabaWhite, Jonathan M.Soria, Delia BeatrizFranca, Carlos AlbertoErben, Mauricio FedericoVibrational SpectroscopyQuantum Chemical CalculationsX-Ray Crystal StructureThioureaThermogravimetryhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular NA...O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular hydrogen-bonding interactions involving the acylthioureamoiety. Compound 2 is further stabilized by p-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV?Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.Fil: Saeed, Aamer. Quaid-i-Azam University; PakistánFil: Ashraf, Saba. Quaid-i-Azam University; PakistánFil: White, Jonathan M.. University of Melbourne; AustraliaFil: Soria, Delia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Franca, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaPergamon-Elsevier Science Ltd2015-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48256Saeed, Aamer; Ashraf, Saba; White, Jonathan M.; Soria, Delia Beatriz; Franca, Carlos Alberto; et al.; Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 150; 11-2015; 409-4181386-1425CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2015.05.068info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1386142515006812info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:42:42Zoai:ri.conicet.gov.ar:11336/48256instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:42:42.365CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
title Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
spellingShingle Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
Saeed, Aamer
Vibrational Spectroscopy
Quantum Chemical Calculations
X-Ray Crystal Structure
Thiourea
Thermogravimetry
title_short Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
title_full Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
title_fullStr Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
title_full_unstemmed Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
title_sort Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
dc.creator.none.fl_str_mv Saeed, Aamer
Ashraf, Saba
White, Jonathan M.
Soria, Delia Beatriz
Franca, Carlos Alberto
Erben, Mauricio Federico
author Saeed, Aamer
author_facet Saeed, Aamer
Ashraf, Saba
White, Jonathan M.
Soria, Delia Beatriz
Franca, Carlos Alberto
Erben, Mauricio Federico
author_role author
author2 Ashraf, Saba
White, Jonathan M.
Soria, Delia Beatriz
Franca, Carlos Alberto
Erben, Mauricio Federico
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Vibrational Spectroscopy
Quantum Chemical Calculations
X-Ray Crystal Structure
Thiourea
Thermogravimetry
topic Vibrational Spectroscopy
Quantum Chemical Calculations
X-Ray Crystal Structure
Thiourea
Thermogravimetry
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular NA...O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular hydrogen-bonding interactions involving the acylthioureamoiety. Compound 2 is further stabilized by p-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV?Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.
Fil: Saeed, Aamer. Quaid-i-Azam University; Pakistán
Fil: Ashraf, Saba. Quaid-i-Azam University; Pakistán
Fil: White, Jonathan M.. University of Melbourne; Australia
Fil: Soria, Delia Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Franca, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular NA...O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular hydrogen-bonding interactions involving the acylthioureamoiety. Compound 2 is further stabilized by p-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV?Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.
publishDate 2015
dc.date.none.fl_str_mv 2015-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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://hdl.handle.net/11336/48256
Saeed, Aamer; Ashraf, Saba; White, Jonathan M.; Soria, Delia Beatriz; Franca, Carlos Alberto; et al.; Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 150; 11-2015; 409-418
1386-1425
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48256
identifier_str_mv Saeed, Aamer; Ashraf, Saba; White, Jonathan M.; Soria, Delia Beatriz; Franca, Carlos Alberto; et al.; Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations; Pergamon-Elsevier Science Ltd; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 150; 11-2015; 409-418
1386-1425
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2015.05.068
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1386142515006812
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.8982525

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