Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers

Autores
Saeed, Aamer; Erben, Mauricio Federico; Florke, Ulrich
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The 1-(2-chlorobenzoyl)-3-(isomeric fluorophenyl)thiourea derivatives (1–3) were prepared by the reaction of 2-chlorobenzoyl isothiocyanate produced in situ with isomeric fluoroanilines in excellent yields. The novel compounds are characterized by multinuclear (1 H and 13C) NMR, GC–MS, elemental analyses and FTIR spectroscopy techniques. Structural and conformational properties of compounds 1–3 are analyzed using a combined approach including X-ray diffraction, vibrational spectra (solid FTIR and FTRaman) and theoretical calculation methods. The crystal structures have been determined by X-ray diffraction methods. The three species crystallize in the monoclinic C2/c space group with and Z = 8 molecules per unit cell. The carbonyl and thiourea groups are almost planar and the conformation adopted by the C@S and the C@O double bonds is antiperiplanar. The crystal lattices show the presence of centrosymmetric dimeric units held by NHS hydrogen bonds stacked along the [0 1 0] plane. The effect of fluorine substitution on the vibrational properties and on the conformational space has been determined by quantum chemical calculations (B3LYP functional in connection with the 6-311+G basis sets) and vibrational spectroscopy.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
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
Fil: Florke, Ulrich. Universitat Paderborn; Alemania
Materia
Síntesis química
Thioureas
Conformational analysis
x-ray diffraction
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:11336/117747
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/117747
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomersSaeed, AamerErben, Mauricio FedericoFlorke, UlrichSíntesis químicaThioureasConformational analysisx-ray diffractionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The 1-(2-chlorobenzoyl)-3-(isomeric fluorophenyl)thiourea derivatives (1–3) were prepared by the reaction of 2-chlorobenzoyl isothiocyanate produced in situ with isomeric fluoroanilines in excellent yields. The novel compounds are characterized by multinuclear (1 H and 13C) NMR, GC–MS, elemental analyses and FTIR spectroscopy techniques. Structural and conformational properties of compounds 1–3 are analyzed using a combined approach including X-ray diffraction, vibrational spectra (solid FTIR and FTRaman) and theoretical calculation methods. The crystal structures have been determined by X-ray diffraction methods. The three species crystallize in the monoclinic C2/c space group with and Z = 8 molecules per unit cell. The carbonyl and thiourea groups are almost planar and the conformation adopted by the C@S and the C@O double bonds is antiperiplanar. The crystal lattices show the presence of centrosymmetric dimeric units held by NHS hydrogen bonds stacked along the [0 1 0] plane. The effect of fluorine substitution on the vibrational properties and on the conformational space has been determined by quantum chemical calculations (B3LYP functional in connection with the 6-311+G basis sets) and vibrational spectroscopy.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: 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"; ArgentinaFil: Florke, Ulrich. Universitat Paderborn; AlemaniaElsevier Science2010-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/117747Saeed, Aamer; Erben, Mauricio Federico; Florke, Ulrich; Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers; Elsevier Science; Journal of Molecular Structure; 982; 10-2010; 91-990022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286010006629info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2010.08.012info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:19:02Zoai:ri.conicet.gov.ar:11336/117747instacron: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:34982025-10-15 15:19:03.199CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
title Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
spellingShingle Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
Saeed, Aamer
Síntesis química
Thioureas
Conformational analysis
x-ray diffraction
title_short Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
title_full Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
title_fullStr Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
title_full_unstemmed Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
title_sort Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers
dc.creator.none.fl_str_mv Saeed, Aamer
Erben, Mauricio Federico
Florke, Ulrich
author Saeed, Aamer
author_facet Saeed, Aamer
Erben, Mauricio Federico
Florke, Ulrich
author_role author
author2 Erben, Mauricio Federico
Florke, Ulrich
author2_role author
author
dc.subject.none.fl_str_mv Síntesis química
Thioureas
Conformational analysis
x-ray diffraction
topic Síntesis química
Thioureas
Conformational analysis
x-ray diffraction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The 1-(2-chlorobenzoyl)-3-(isomeric fluorophenyl)thiourea derivatives (1–3) were prepared by the reaction of 2-chlorobenzoyl isothiocyanate produced in situ with isomeric fluoroanilines in excellent yields. The novel compounds are characterized by multinuclear (1 H and 13C) NMR, GC–MS, elemental analyses and FTIR spectroscopy techniques. Structural and conformational properties of compounds 1–3 are analyzed using a combined approach including X-ray diffraction, vibrational spectra (solid FTIR and FTRaman) and theoretical calculation methods. The crystal structures have been determined by X-ray diffraction methods. The three species crystallize in the monoclinic C2/c space group with and Z = 8 molecules per unit cell. The carbonyl and thiourea groups are almost planar and the conformation adopted by the C@S and the C@O double bonds is antiperiplanar. The crystal lattices show the presence of centrosymmetric dimeric units held by NHS hydrogen bonds stacked along the [0 1 0] plane. The effect of fluorine substitution on the vibrational properties and on the conformational space has been determined by quantum chemical calculations (B3LYP functional in connection with the 6-311+G basis sets) and vibrational spectroscopy.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
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
Fil: Florke, Ulrich. Universitat Paderborn; Alemania
description The 1-(2-chlorobenzoyl)-3-(isomeric fluorophenyl)thiourea derivatives (1–3) were prepared by the reaction of 2-chlorobenzoyl isothiocyanate produced in situ with isomeric fluoroanilines in excellent yields. The novel compounds are characterized by multinuclear (1 H and 13C) NMR, GC–MS, elemental analyses and FTIR spectroscopy techniques. Structural and conformational properties of compounds 1–3 are analyzed using a combined approach including X-ray diffraction, vibrational spectra (solid FTIR and FTRaman) and theoretical calculation methods. The crystal structures have been determined by X-ray diffraction methods. The three species crystallize in the monoclinic C2/c space group with and Z = 8 molecules per unit cell. The carbonyl and thiourea groups are almost planar and the conformation adopted by the C@S and the C@O double bonds is antiperiplanar. The crystal lattices show the presence of centrosymmetric dimeric units held by NHS hydrogen bonds stacked along the [0 1 0] plane. The effect of fluorine substitution on the vibrational properties and on the conformational space has been determined by quantum chemical calculations (B3LYP functional in connection with the 6-311+G basis sets) and vibrational spectroscopy.
publishDate 2010
dc.date.none.fl_str_mv 2010-10
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/11336/117747
Saeed, Aamer; Erben, Mauricio Federico; Florke, Ulrich; Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers; Elsevier Science; Journal of Molecular Structure; 982; 10-2010; 91-99
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/117747
identifier_str_mv Saeed, Aamer; Erben, Mauricio Federico; Florke, Ulrich; Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers; Elsevier Science; Journal of Molecular Structure; 982; 10-2010; 91-99
0022-2860
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286010006629
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2010.08.012
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
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 13.22299

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