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
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/129696
Ver los metadatos del registro completo
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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 Técnicas2025-10-22T11:22:47Zoai: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:34982025-10-22 11:22:48.202CONICET 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 |
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info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
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article |
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publishedVersion |
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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 |
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eng |
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eng |
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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 |
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info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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openAccess |
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https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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application/pdf application/pdf |
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Elsevier Science |
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Elsevier Science |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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