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

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...

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Autores principales: Fraga, Guido Gustavo, Colasurdo, Diego Damián, Santiago, Cintia Cecilia, Ponzinibbio, Agustín, Sasiambarrena, Leandro Daniel
Formato: Articulo
Lenguaje:Inglés
Publicado: 2022
Materias:
Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/172502
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-172502
record_format dspace
spelling I19-R120-10915-1725022024-11-04T20:10:38Z http://sedici.unlp.edu.ar/handle/10915/172502 Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study Fraga, Guido Gustavo Colasurdo, Diego Damián Santiago, Cintia Cecilia Ponzinibbio, Agustín Sasiambarrena, Leandro Daniel 2022-08-05 2024-11-04T15:48:03Z en Química Chloroacetamides Rotamers NMR ASIS effect Molecular modeling 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 Articulo Articulo http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) application/pdf
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
spellingShingle Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
Fraga, Guido Gustavo
Colasurdo, Diego Damián
Santiago, Cintia Cecilia
Ponzinibbio, Agustín
Sasiambarrena, Leandro Daniel
Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
topic_facet Química
Chloroacetamides
Rotamers
NMR
ASIS effect
Molecular modeling
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.
format Articulo
Articulo
author Fraga, Guido Gustavo
Colasurdo, Diego Damián
Santiago, Cintia Cecilia
Ponzinibbio, Agustín
Sasiambarrena, Leandro Daniel
author_facet Fraga, Guido Gustavo
Colasurdo, Diego Damián
Santiago, Cintia Cecilia
Ponzinibbio, Agustín
Sasiambarrena, Leandro Daniel
author_sort Fraga, Guido Gustavo
title Rotamerization equilibrium in novel N,N-disubstituted chloroacetamides: An NMR spectroscopic study
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
publishDate 2022
url http://sedici.unlp.edu.ar/handle/10915/172502
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