The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

Autores
Saeed, Aamer; Florke, Ulrich; Erben, Mauricio Federico
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Three novel 1-(adamantane-1-carbonyl) thioureas were synthesized by the reaction of adamantyl isothiocyante with corresponding amines and fully characterized by spectroscopy methods. Two isomeric species, i.e. 1-(adamantane-1-carbonyl)-3-(3-nitrophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)- 3-(4-nitrophenyl)thiourea (2), are structurally characterized and a third related compound, namely 1-(adamantane-1-carbonyl)-3,3-(methyl-phenyl)thiourea (3) has been also included for assessing the role of the nitrogen substitution on the structural properties. As determined by X-ray analysis, compounds 1 and 2 exhibit the S conformation with the C@O and C@S double bonds in a pseudo-antiperiplanar orientation, whereas the U form is found for compound 3. These conformational features are mainly dictated by the substitution degree on the thiourea core and the ability of forming an intra-molecular NAHO@C hydrogen bond for mono-substituted analogues 1 and 2. These dissimilar interactions affect the vibrational properties, which have been determined by infrared and Raman spectroscopies and quantum chemical calculations at the B3LYP/6-311++G** level of approximation.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Florke, Ulrich. Universität Paderborn; Alemania
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
Acyl Thioureas
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Hydrogen Bond
Conformational Analysis
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:11336/24801
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/24801
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureasSaeed, AamerFlorke, UlrichErben, Mauricio FedericoAcyl ThioureasVibrational SpectroscopyQuantum Chemical CalculationsCrystal StructureHydrogen BondConformational Analysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Three novel 1-(adamantane-1-carbonyl) thioureas were synthesized by the reaction of adamantyl isothiocyante with corresponding amines and fully characterized by spectroscopy methods. Two isomeric species, i.e. 1-(adamantane-1-carbonyl)-3-(3-nitrophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)- 3-(4-nitrophenyl)thiourea (2), are structurally characterized and a third related compound, namely 1-(adamantane-1-carbonyl)-3,3-(methyl-phenyl)thiourea (3) has been also included for assessing the role of the nitrogen substitution on the structural properties. As determined by X-ray analysis, compounds 1 and 2 exhibit the S conformation with the C@O and C@S double bonds in a pseudo-antiperiplanar orientation, whereas the U form is found for compound 3. These conformational features are mainly dictated by the substitution degree on the thiourea core and the ability of forming an intra-molecular NAHO@C hydrogen bond for mono-substituted analogues 1 and 2. These dissimilar interactions affect the vibrational properties, which have been determined by infrared and Raman spectroscopies and quantum chemical calculations at the B3LYP/6-311++G** level of approximation.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Florke, Ulrich. Universität Paderborn; AlemaniaFil: 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"; ArgentinaElsevier Science2014-05-22info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/24801Saeed, Aamer; Florke, Ulrich; Erben, Mauricio Federico; The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas; Elsevier Science; Journal of Molecular Structure; 1065-1066; 22-5-2014; 150-1590022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2014.03.002info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022286014002488info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:06:09Zoai:ri.conicet.gov.ar:11336/24801instacron: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:34982025-09-10 13:06:09.995CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
title The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
spellingShingle The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
Saeed, Aamer
Acyl Thioureas
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Hydrogen Bond
Conformational Analysis
title_short The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
title_full The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
title_fullStr The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
title_full_unstemmed The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
title_sort The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas
dc.creator.none.fl_str_mv Saeed, Aamer
Florke, Ulrich
Erben, Mauricio Federico
author Saeed, Aamer
author_facet Saeed, Aamer
Florke, Ulrich
Erben, Mauricio Federico
author_role author
author2 Florke, Ulrich
Erben, Mauricio Federico
author2_role author
author
dc.subject.none.fl_str_mv Acyl Thioureas
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Hydrogen Bond
Conformational Analysis
topic Acyl Thioureas
Vibrational Spectroscopy
Quantum Chemical Calculations
Crystal Structure
Hydrogen Bond
Conformational Analysis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Three novel 1-(adamantane-1-carbonyl) thioureas were synthesized by the reaction of adamantyl isothiocyante with corresponding amines and fully characterized by spectroscopy methods. Two isomeric species, i.e. 1-(adamantane-1-carbonyl)-3-(3-nitrophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)- 3-(4-nitrophenyl)thiourea (2), are structurally characterized and a third related compound, namely 1-(adamantane-1-carbonyl)-3,3-(methyl-phenyl)thiourea (3) has been also included for assessing the role of the nitrogen substitution on the structural properties. As determined by X-ray analysis, compounds 1 and 2 exhibit the S conformation with the C@O and C@S double bonds in a pseudo-antiperiplanar orientation, whereas the U form is found for compound 3. These conformational features are mainly dictated by the substitution degree on the thiourea core and the ability of forming an intra-molecular NAHO@C hydrogen bond for mono-substituted analogues 1 and 2. These dissimilar interactions affect the vibrational properties, which have been determined by infrared and Raman spectroscopies and quantum chemical calculations at the B3LYP/6-311++G** level of approximation.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Florke, Ulrich. Universität Paderborn; Alemania
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 Three novel 1-(adamantane-1-carbonyl) thioureas were synthesized by the reaction of adamantyl isothiocyante with corresponding amines and fully characterized by spectroscopy methods. Two isomeric species, i.e. 1-(adamantane-1-carbonyl)-3-(3-nitrophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)- 3-(4-nitrophenyl)thiourea (2), are structurally characterized and a third related compound, namely 1-(adamantane-1-carbonyl)-3,3-(methyl-phenyl)thiourea (3) has been also included for assessing the role of the nitrogen substitution on the structural properties. As determined by X-ray analysis, compounds 1 and 2 exhibit the S conformation with the C@O and C@S double bonds in a pseudo-antiperiplanar orientation, whereas the U form is found for compound 3. These conformational features are mainly dictated by the substitution degree on the thiourea core and the ability of forming an intra-molecular NAHO@C hydrogen bond for mono-substituted analogues 1 and 2. These dissimilar interactions affect the vibrational properties, which have been determined by infrared and Raman spectroscopies and quantum chemical calculations at the B3LYP/6-311++G** level of approximation.
publishDate 2014
dc.date.none.fl_str_mv 2014-05-22
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/11336/24801
Saeed, Aamer; Florke, Ulrich; Erben, Mauricio Federico; The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas; Elsevier Science; Journal of Molecular Structure; 1065-1066; 22-5-2014; 150-159
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/24801
identifier_str_mv Saeed, Aamer; Florke, Ulrich; Erben, Mauricio Federico; The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas; Elsevier Science; Journal of Molecular Structure; 1065-1066; 22-5-2014; 150-159
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.2014.03.002
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022286014002488
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
_version_ 1842980248106303488
score 12.993085

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