Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas

Autores
Saeed, Aamer; Ashraf, Zaman; Erben, Mauricio Federico; Simpson, Jim
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
1-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1, and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2, were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular NH⋯O and intermolecular NH⋯S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(CO) and ν(CS) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular NH⋯OC hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl⋯Cl halogen bond.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Ashraf, Zaman. Allama Iqbal 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: Simpson, Jim. University Of Otago; Canadá
Materia
1-Acyl-Thiourea
Synthesis
Crystal Structure
Vibrational Analysis
Hydrogen Bonding
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:11336/48253
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureasSaeed, AamerAshraf, ZamanErben, Mauricio FedericoSimpson, Jim1-Acyl-ThioureaSynthesisCrystal StructureVibrational AnalysisHydrogen Bondinghttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/11-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1, and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2, were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular NH⋯O and intermolecular NH⋯S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(CO) and ν(CS) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular NH⋯OC hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl⋯Cl halogen bond.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Ashraf, Zaman. Allama Iqbal 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: Simpson, Jim. University Of Otago; CanadáElsevier Science2017-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48253Saeed, Aamer; Ashraf, Zaman; Erben, Mauricio Federico; Simpson, Jim; Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas; Elsevier Science; Journal of Molecular Structure; 1129; 2-2017; 283-2910022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2016.09.039info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286016309668info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:57:34Zoai:ri.conicet.gov.ar:11336/48253instacron: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:34982025-09-29 09:57:34.302CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
title Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
spellingShingle Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
Saeed, Aamer
1-Acyl-Thiourea
Synthesis
Crystal Structure
Vibrational Analysis
Hydrogen Bonding
title_short Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
title_full Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
title_fullStr Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
title_full_unstemmed Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
title_sort Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
dc.creator.none.fl_str_mv Saeed, Aamer
Ashraf, Zaman
Erben, Mauricio Federico
Simpson, Jim
author Saeed, Aamer
author_facet Saeed, Aamer
Ashraf, Zaman
Erben, Mauricio Federico
Simpson, Jim
author_role author
author2 Ashraf, Zaman
Erben, Mauricio Federico
Simpson, Jim
author2_role author
author
author
dc.subject.none.fl_str_mv 1-Acyl-Thiourea
Synthesis
Crystal Structure
Vibrational Analysis
Hydrogen Bonding
topic 1-Acyl-Thiourea
Synthesis
Crystal Structure
Vibrational Analysis
Hydrogen Bonding
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 1-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1, and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2, were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular NH⋯O and intermolecular NH⋯S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(CO) and ν(CS) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular NH⋯OC hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl⋯Cl halogen bond.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Ashraf, Zaman. Allama Iqbal 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: Simpson, Jim. University Of Otago; Canadá
description 1-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1, and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2, were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular NH⋯O and intermolecular NH⋯S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(CO) and ν(CS) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular NH⋯OC hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl⋯Cl halogen bond.
publishDate 2017
dc.date.none.fl_str_mv 2017-02
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/11336/48253
Saeed, Aamer; Ashraf, Zaman; Erben, Mauricio Federico; Simpson, Jim; Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas; Elsevier Science; Journal of Molecular Structure; 1129; 2-2017; 283-291
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48253
identifier_str_mv Saeed, Aamer; Ashraf, Zaman; Erben, Mauricio Federico; Simpson, Jim; Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas; Elsevier Science; Journal of Molecular Structure; 1129; 2-2017; 283-291
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/doi/10.1016/j.molstruc.2016.09.039
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286016309668
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 13.070432

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