Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium

Autores
Gholivand, Khodayar; Farshadian, Sedighe; Erben, Mauricio Federico; Della Vedova, Carlos Omar
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new phosphonic diamide containing thiazolyl rings, N,N0 bis(2-thiazolyl) phenylphosphonic diamide, with general formula H5C6P(O)[NHCN(CH)2S]2 (1), was synthesized and characterized by NMR, IR, UV, EI mass-spectrometry and elemental analysis. The X-ray diffraction structure obtained for 1 shows that the crystalline compound exists in the imine form, forming centro-symmetric dimers which are produced by intermolecular cooperative hydrogen bonds leading to a two-dimensional polymeric chain. The preferred tautomeric and conformational equilibria have also been identified in solution. Thus, a tautomeric equilibrium of 97:3% between the amine:imine form is observed in DMSO-d6. Structural and conformational properties are analyzed using a combined approach involving crystallographic data, vibrational spectra and theoretical calculations at the B3LYP and MP2 (with 6-311++G and CBSB7 basis sets) level of approximations.
Fil: Gholivand, Khodayar. Tarbiat Modares University; Irán
Fil: Farshadian, Sedighe. Tarbiat Modares University; Irán
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: Della Vedova, Carlos Omar. 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
Phosponic diamides
Thizzolyl groups
tautomeric equilibrium
synthesis
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:11336/129696
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/129696
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibriumGholivand, KhodayarFarshadian, SedigheErben, Mauricio FedericoDella Vedova, Carlos OmarPhosponic diamidesThizzolyl groupstautomeric equilibriumsynthesishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new phosphonic diamide containing thiazolyl rings, N,N0 bis(2-thiazolyl) phenylphosphonic diamide, with general formula H5C6P(O)[NHCN(CH)2S]2 (1), was synthesized and characterized by NMR, IR, UV, EI mass-spectrometry and elemental analysis. The X-ray diffraction structure obtained for 1 shows that the crystalline compound exists in the imine form, forming centro-symmetric dimers which are produced by intermolecular cooperative hydrogen bonds leading to a two-dimensional polymeric chain. The preferred tautomeric and conformational equilibria have also been identified in solution. Thus, a tautomeric equilibrium of 97:3% between the amine:imine form is observed in DMSO-d6. Structural and conformational properties are analyzed using a combined approach involving crystallographic data, vibrational spectra and theoretical calculations at the B3LYP and MP2 (with 6-311++G and CBSB7 basis sets) level of approximations.Fil: Gholivand, Khodayar. Tarbiat Modares University; IránFil: Farshadian, Sedighe. Tarbiat Modares University; IránFil: 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: Della Vedova, Carlos Omar. 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 Science2010-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/129696Gholivand, Khodayar; Farshadian, Sedighe; Erben, Mauricio Federico; Della Vedova, Carlos Omar; Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium; Elsevier Science; Journal of Molecular Structure; 978; 1-3; 6-2010; 67-730022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2009.12.018info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286009007819?via%3Dihubinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:53:26Zoai:ri.conicet.gov.ar:11336/129696instacron: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 09:53:26.427CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
title Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
spellingShingle Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
Gholivand, Khodayar
Phosponic diamides
Thizzolyl groups
tautomeric equilibrium
synthesis
title_short Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
title_full Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
title_fullStr Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
title_full_unstemmed Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
title_sort Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium
dc.creator.none.fl_str_mv Gholivand, Khodayar
Farshadian, Sedighe
Erben, Mauricio Federico
Della Vedova, Carlos Omar
author Gholivand, Khodayar
author_facet Gholivand, Khodayar
Farshadian, Sedighe
Erben, Mauricio Federico
Della Vedova, Carlos Omar
author_role author
author2 Farshadian, Sedighe
Erben, Mauricio Federico
Della Vedova, Carlos Omar
author2_role author
author
author
dc.subject.none.fl_str_mv Phosponic diamides
Thizzolyl groups
tautomeric equilibrium
synthesis
topic Phosponic diamides
Thizzolyl groups
tautomeric equilibrium
synthesis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new phosphonic diamide containing thiazolyl rings, N,N0 bis(2-thiazolyl) phenylphosphonic diamide, with general formula H5C6P(O)[NHCN(CH)2S]2 (1), was synthesized and characterized by NMR, IR, UV, EI mass-spectrometry and elemental analysis. The X-ray diffraction structure obtained for 1 shows that the crystalline compound exists in the imine form, forming centro-symmetric dimers which are produced by intermolecular cooperative hydrogen bonds leading to a two-dimensional polymeric chain. The preferred tautomeric and conformational equilibria have also been identified in solution. Thus, a tautomeric equilibrium of 97:3% between the amine:imine form is observed in DMSO-d6. Structural and conformational properties are analyzed using a combined approach involving crystallographic data, vibrational spectra and theoretical calculations at the B3LYP and MP2 (with 6-311++G and CBSB7 basis sets) level of approximations.
Fil: Gholivand, Khodayar. Tarbiat Modares University; Irán
Fil: Farshadian, Sedighe. Tarbiat Modares University; Irán
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: Della Vedova, Carlos Omar. 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 A new phosphonic diamide containing thiazolyl rings, N,N0 bis(2-thiazolyl) phenylphosphonic diamide, with general formula H5C6P(O)[NHCN(CH)2S]2 (1), was synthesized and characterized by NMR, IR, UV, EI mass-spectrometry and elemental analysis. The X-ray diffraction structure obtained for 1 shows that the crystalline compound exists in the imine form, forming centro-symmetric dimers which are produced by intermolecular cooperative hydrogen bonds leading to a two-dimensional polymeric chain. The preferred tautomeric and conformational equilibria have also been identified in solution. Thus, a tautomeric equilibrium of 97:3% between the amine:imine form is observed in DMSO-d6. Structural and conformational properties are analyzed using a combined approach involving crystallographic data, vibrational spectra and theoretical calculations at the B3LYP and MP2 (with 6-311++G and CBSB7 basis sets) level of approximations.
publishDate 2010
dc.date.none.fl_str_mv 2010-06
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/11336/129696
Gholivand, Khodayar; Farshadian, Sedighe; Erben, Mauricio Federico; Della Vedova, Carlos Omar; Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium; Elsevier Science; Journal of Molecular Structure; 978; 1-3; 6-2010; 67-73
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/129696
identifier_str_mv Gholivand, Khodayar; Farshadian, Sedighe; Erben, Mauricio Federico; Della Vedova, Carlos Omar; Synthesis and characterization of the first phosphonic diamide containing thiazolyl groups: Structural properties and tautomeric equilibrium; Elsevier Science; Journal of Molecular Structure; 978; 1-3; 6-2010; 67-73
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.2009.12.018
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286009007819?via%3Dihub
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_ 1844613632456916992
score 13.070432

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