Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas

Autores
Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
1-(Adamantane-1-carbonyl)-3-(2,4-dichlorophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)-3-(2-bromo-4,6-difluorophenyl)thiourea (2) were synthesized by the reaction of adamantane-1-carbonyl chloride with ammonium thiocyanate to afford the adamantane-1-carbonylisothiocyanate in situ followed by treatment with suitable halogenated anilines. The structures of the products were established by elemental analyses, Fourier transform infrared spectroscopy (FTIR), 1H, 13C nuclear magnetic resonance (NMR), mass spectroscopy and single crystal X-ray diffraction study. Bond lengths and angles show the usual values. All of three condensed cyclohexane rings of the adamantane residues adopt the usual chair conformation. The molecular conformation of 1 and 2 is stabilized by an intramolecular (NH⋯OC) hydrogen bond which forms a pseudo-six-membered ring. Structural features have been complemented with the joint analysis of the FTIR and FT-Raman spectra along with quantum chemical calculations at the B3LYP/6-311++G- level.
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: Bolte, Michael. Goethe Universitat Frankfurt; Alemania
Materia
1-(Adamantane-1-Carbonyl)-3-(Halophenyl)Thioureas
Crystal Structure
Hydrogen Bond
Quantum Chemical Calculations
Vibrational Spectroscopy
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/82980
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/82980
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureasSaeed, AamerErben, Mauricio FedericoBolte, Michael1-(Adamantane-1-Carbonyl)-3-(Halophenyl)ThioureasCrystal StructureHydrogen BondQuantum Chemical CalculationsVibrational Spectroscopyhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/11-(Adamantane-1-carbonyl)-3-(2,4-dichlorophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)-3-(2-bromo-4,6-difluorophenyl)thiourea (2) were synthesized by the reaction of adamantane-1-carbonyl chloride with ammonium thiocyanate to afford the adamantane-1-carbonylisothiocyanate in situ followed by treatment with suitable halogenated anilines. The structures of the products were established by elemental analyses, Fourier transform infrared spectroscopy (FTIR), 1H, 13C nuclear magnetic resonance (NMR), mass spectroscopy and single crystal X-ray diffraction study. Bond lengths and angles show the usual values. All of three condensed cyclohexane rings of the adamantane residues adopt the usual chair conformation. The molecular conformation of 1 and 2 is stabilized by an intramolecular (NH⋯OC) hydrogen bond which forms a pseudo-six-membered ring. Structural features have been complemented with the joint analysis of the FTIR and FT-Raman spectra along with quantum chemical calculations at the B3LYP/6-311++G- level.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: Bolte, Michael. Goethe Universitat Frankfurt; AlemaniaElsevier2013-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/82980Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael; Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas; Elsevier; Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy; 102; 2-2013; 408-4130584-8539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1386142512010591info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2012.10.043info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:23:47Zoai:ri.conicet.gov.ar:11336/82980instacron: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 14:23:47.667CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
title Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
spellingShingle Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
Saeed, Aamer
1-(Adamantane-1-Carbonyl)-3-(Halophenyl)Thioureas
Crystal Structure
Hydrogen Bond
Quantum Chemical Calculations
Vibrational Spectroscopy
title_short Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
title_full Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
title_fullStr Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
title_full_unstemmed Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
title_sort Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas
dc.creator.none.fl_str_mv Saeed, Aamer
Erben, Mauricio Federico
Bolte, Michael
author Saeed, Aamer
author_facet Saeed, Aamer
Erben, Mauricio Federico
Bolte, Michael
author_role author
author2 Erben, Mauricio Federico
Bolte, Michael
author2_role author
author
dc.subject.none.fl_str_mv 1-(Adamantane-1-Carbonyl)-3-(Halophenyl)Thioureas
Crystal Structure
Hydrogen Bond
Quantum Chemical Calculations
Vibrational Spectroscopy
topic 1-(Adamantane-1-Carbonyl)-3-(Halophenyl)Thioureas
Crystal Structure
Hydrogen Bond
Quantum Chemical Calculations
Vibrational Spectroscopy
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-(Adamantane-1-carbonyl)-3-(2,4-dichlorophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)-3-(2-bromo-4,6-difluorophenyl)thiourea (2) were synthesized by the reaction of adamantane-1-carbonyl chloride with ammonium thiocyanate to afford the adamantane-1-carbonylisothiocyanate in situ followed by treatment with suitable halogenated anilines. The structures of the products were established by elemental analyses, Fourier transform infrared spectroscopy (FTIR), 1H, 13C nuclear magnetic resonance (NMR), mass spectroscopy and single crystal X-ray diffraction study. Bond lengths and angles show the usual values. All of three condensed cyclohexane rings of the adamantane residues adopt the usual chair conformation. The molecular conformation of 1 and 2 is stabilized by an intramolecular (NH⋯OC) hydrogen bond which forms a pseudo-six-membered ring. Structural features have been complemented with the joint analysis of the FTIR and FT-Raman spectra along with quantum chemical calculations at the B3LYP/6-311++G- level.
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: Bolte, Michael. Goethe Universitat Frankfurt; Alemania
description 1-(Adamantane-1-carbonyl)-3-(2,4-dichlorophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)-3-(2-bromo-4,6-difluorophenyl)thiourea (2) were synthesized by the reaction of adamantane-1-carbonyl chloride with ammonium thiocyanate to afford the adamantane-1-carbonylisothiocyanate in situ followed by treatment with suitable halogenated anilines. The structures of the products were established by elemental analyses, Fourier transform infrared spectroscopy (FTIR), 1H, 13C nuclear magnetic resonance (NMR), mass spectroscopy and single crystal X-ray diffraction study. Bond lengths and angles show the usual values. All of three condensed cyclohexane rings of the adamantane residues adopt the usual chair conformation. The molecular conformation of 1 and 2 is stabilized by an intramolecular (NH⋯OC) hydrogen bond which forms a pseudo-six-membered ring. Structural features have been complemented with the joint analysis of the FTIR and FT-Raman spectra along with quantum chemical calculations at the B3LYP/6-311++G- level.
publishDate 2013
dc.date.none.fl_str_mv 2013-02
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/11336/82980
Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael; Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas; Elsevier; Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy; 102; 2-2013; 408-413
0584-8539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/82980
identifier_str_mv Saeed, Aamer; Erben, Mauricio Federico; Bolte, Michael; Synthesis, structural and vibrational properties of 1-(adamantane-1- carbonyl)-3-halophenyl thioureas; Elsevier; Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy; 102; 2-2013; 408-413
0584-8539
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/pii/S1386142512010591
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2012.10.043
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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_ 1846082652569862144
score 13.22299

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