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
.jpg)
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/172502
Ver los metadatos del registro completo
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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:UNLP2025-10-22T17:27:09Zoai: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:13292025-10-22 17:27:10.233SEDICI (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 |
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2022-08-05 |
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info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Articulo http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
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http://sedici.unlp.edu.ar/handle/10915/172502 |
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eng |
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info:eu-repo/semantics/altIdentifier/issn/0022-2860 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2022.132892 |
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