NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides

Autores
Orelli, Liliana Raquel; Gruber, Nadia
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The complete 1H and 13C NMR assignments of a series of tertiary phosphonoacetamides (1) with different N-substitution patterns are reported. N,N-Dialkyl derivatives show two sets of signals due to hindered rotation of the (O)C{single bond}N bond, which originate E/Z diastereoisomers for unsymmetrically N,N-disubstituted derivatives. Complete assignment of the 1H NMR resonances of both rotamers was made on the basis of the magnitude of the diamagnetic shifts (Δδ) experienced by the signals on changing the solvent from CDCl3 to C6D6, and confirmed in the corresponding NOESY spectra. Differential assignment of the 13C NMR signals was performed by HSQC experiments. N-Alkyl-N-phenyl phosphonoacetamides show a unique set of signals corresponding to the E isomers as disclosed by NOESY experiments.
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Materia
AMIDES
HINDERED ROTATION
NMR
PHOSPHONOACETAMIDES
PHOSPHORUS COMPOUNDS
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:11336/114228
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamidesOrelli, Liliana RaquelGruber, NadiaAMIDESHINDERED ROTATIONNMRPHOSPHONOACETAMIDESPHOSPHORUS COMPOUNDShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The complete 1H and 13C NMR assignments of a series of tertiary phosphonoacetamides (1) with different N-substitution patterns are reported. N,N-Dialkyl derivatives show two sets of signals due to hindered rotation of the (O)C{single bond}N bond, which originate E/Z diastereoisomers for unsymmetrically N,N-disubstituted derivatives. Complete assignment of the 1H NMR resonances of both rotamers was made on the basis of the magnitude of the diamagnetic shifts (Δδ) experienced by the signals on changing the solvent from CDCl3 to C6D6, and confirmed in the corresponding NOESY spectra. Differential assignment of the 13C NMR signals was performed by HSQC experiments. N-Alkyl-N-phenyl phosphonoacetamides show a unique set of signals corresponding to the E isomers as disclosed by NOESY experiments.Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaElsevier Science2009-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/114228Orelli, Liliana Raquel; Gruber, Nadia; NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides; Elsevier Science; Journal of Molecular Structure; 921; 1-3; 3-2009; 215-2180022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286009000143info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2008.12.070info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:34:16Zoai:ri.conicet.gov.ar:11336/114228instacron: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 09:34:16.549CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
title NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
spellingShingle NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
Orelli, Liliana Raquel
AMIDES
HINDERED ROTATION
NMR
PHOSPHONOACETAMIDES
PHOSPHORUS COMPOUNDS
title_short NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
title_full NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
title_fullStr NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
title_full_unstemmed NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
title_sort NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides
dc.creator.none.fl_str_mv Orelli, Liliana Raquel
Gruber, Nadia
author Orelli, Liliana Raquel
author_facet Orelli, Liliana Raquel
Gruber, Nadia
author_role author
author2 Gruber, Nadia
author2_role author
dc.subject.none.fl_str_mv AMIDES
HINDERED ROTATION
NMR
PHOSPHONOACETAMIDES
PHOSPHORUS COMPOUNDS
topic AMIDES
HINDERED ROTATION
NMR
PHOSPHONOACETAMIDES
PHOSPHORUS COMPOUNDS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The complete 1H and 13C NMR assignments of a series of tertiary phosphonoacetamides (1) with different N-substitution patterns are reported. N,N-Dialkyl derivatives show two sets of signals due to hindered rotation of the (O)C{single bond}N bond, which originate E/Z diastereoisomers for unsymmetrically N,N-disubstituted derivatives. Complete assignment of the 1H NMR resonances of both rotamers was made on the basis of the magnitude of the diamagnetic shifts (Δδ) experienced by the signals on changing the solvent from CDCl3 to C6D6, and confirmed in the corresponding NOESY spectra. Differential assignment of the 13C NMR signals was performed by HSQC experiments. N-Alkyl-N-phenyl phosphonoacetamides show a unique set of signals corresponding to the E isomers as disclosed by NOESY experiments.
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Gruber, Nadia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
description The complete 1H and 13C NMR assignments of a series of tertiary phosphonoacetamides (1) with different N-substitution patterns are reported. N,N-Dialkyl derivatives show two sets of signals due to hindered rotation of the (O)C{single bond}N bond, which originate E/Z diastereoisomers for unsymmetrically N,N-disubstituted derivatives. Complete assignment of the 1H NMR resonances of both rotamers was made on the basis of the magnitude of the diamagnetic shifts (Δδ) experienced by the signals on changing the solvent from CDCl3 to C6D6, and confirmed in the corresponding NOESY spectra. Differential assignment of the 13C NMR signals was performed by HSQC experiments. N-Alkyl-N-phenyl phosphonoacetamides show a unique set of signals corresponding to the E isomers as disclosed by NOESY experiments.
publishDate 2009
dc.date.none.fl_str_mv 2009-03
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/11336/114228
Orelli, Liliana Raquel; Gruber, Nadia; NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides; Elsevier Science; Journal of Molecular Structure; 921; 1-3; 3-2009; 215-218
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/114228
identifier_str_mv Orelli, Liliana Raquel; Gruber, Nadia; NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides; Elsevier Science; Journal of Molecular Structure; 921; 1-3; 3-2009; 215-218
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/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286009000143
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2008.12.070
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
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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