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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Detalles Bibliográficos
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
Descripción
Sumario: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.

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