Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study

Autores
Fraga, Guido Gustavo; Colasurdo, Diego Damián; Santiago, Cintia Cecilia; Ponzinibbio, Agustín; Sasiambarrena, Leandro Daniel
Año de publicación
2022
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We studied the E/Z rotamers of new N-substituted 2–chloro-N-(2-nitrobenzyl)acetamides by applying 1HNMR and 13C-NMR techniques. The restricted rotation around the amide bond generates a mixture of E/Z diastereomers visualized as a set of appreciably separated signals in the NMR spectra. In order to assign each signal to its corresponding rotamer, the criterion of the anisotropic solvent-induced shift (ASIS) effect, observed in the 1H-NMR spectra, was used. The effects of solvent and substituent on the relative E/Z ratios were also analyzed.
Centro de Estudios de Compuestos Orgánicos
Materia
Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/172502

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repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic studyFraga, Guido GustavoColasurdo, Diego DamiánSantiago, Cintia CeciliaPonzinibbio, AgustínSasiambarrena, Leandro DanielQuímicaChloroacetamidesRotamersNMRASIS effectMolecular modelingWe studied the E/Z rotamers of new N-substituted 2–chloro-N-(2-nitrobenzyl)acetamides by applying 1HNMR and 13C-NMR techniques. The restricted rotation around the amide bond generates a mixture of E/Z diastereomers visualized as a set of appreciably separated signals in the NMR spectra. In order to assign each signal to its corresponding rotamer, the criterion of the anisotropic solvent-induced shift (ASIS) effect, observed in the 1H-NMR spectra, was used. The effects of solvent and substituent on the relative E/Z ratios were also analyzed.Centro de Estudios de Compuestos Orgánicos2022-08-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://sedici.unlp.edu.ar/handle/10915/172502enginfo:eu-repo/semantics/altIdentifier/issn/0022-2860info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2022.132892info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:46:19Zoai:sedici.unlp.edu.ar:10915/172502Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:46:19.226SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
title Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
spellingShingle Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
Fraga, Guido Gustavo
Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
title_short Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
title_full Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
title_fullStr Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
title_full_unstemmed Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
title_sort Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
dc.creator.none.fl_str_mv Fraga, Guido Gustavo
Colasurdo, Diego Damián
Santiago, Cintia Cecilia
Ponzinibbio, Agustín
Sasiambarrena, Leandro Daniel
author Fraga, Guido Gustavo
author_facet Fraga, Guido Gustavo
Colasurdo, Diego Damián
Santiago, Cintia Cecilia
Ponzinibbio, Agustín
Sasiambarrena, Leandro Daniel
author_role author
author2 Colasurdo, Diego Damián
Santiago, Cintia Cecilia
Ponzinibbio, Agustín
Sasiambarrena, Leandro Daniel
author2_role author
author
author
author
dc.subject.none.fl_str_mv Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
topic Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
dc.description.none.fl_txt_mv We studied the E/Z rotamers of new N-substituted 2–chloro-N-(2-nitrobenzyl)acetamides by applying 1HNMR and 13C-NMR techniques. The restricted rotation around the amide bond generates a mixture of E/Z diastereomers visualized as a set of appreciably separated signals in the NMR spectra. In order to assign each signal to its corresponding rotamer, the criterion of the anisotropic solvent-induced shift (ASIS) effect, observed in the 1H-NMR spectra, was used. The effects of solvent and substituent on the relative E/Z ratios were also analyzed.
Centro de Estudios de Compuestos Orgánicos
description We studied the E/Z rotamers of new N-substituted 2–chloro-N-(2-nitrobenzyl)acetamides by applying 1HNMR and 13C-NMR techniques. The restricted rotation around the amide bond generates a mixture of E/Z diastereomers visualized as a set of appreciably separated signals in the NMR spectra. In order to assign each signal to its corresponding rotamer, the criterion of the anisotropic solvent-induced shift (ASIS) effect, observed in the 1H-NMR spectra, was used. The effects of solvent and substituent on the relative E/Z ratios were also analyzed.
publishDate 2022
dc.date.none.fl_str_mv 2022-08-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
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url http://sedici.unlp.edu.ar/handle/10915/172502
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/0022-2860
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2022.132892
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
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instname_str Universidad Nacional de La Plata
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repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
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