Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations

In this study, the conformational behavior of N-benzyl-N-(furan-2-ylmethyl) acetamide in chloroform was addressed by using a combined experimental/theoretical strategy using NMR spectroscopy and quantum chemical calculations. The 1H and 13C one‑dimensional NMR spectra, as well as the two-dimensional...

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Autores principales: Corredor Montaña, Jeisson D., Loaiza, Alix E., Romanelli, Gustavo Pablo, De Waele, Isabelle, Tobón, Yeny A., Gómez Castaño, Jovanny A.
Formato: Articulo
Lenguaje:Inglés
Publicado: 2021
Materias:
Química
Density Functional Theory
conformational analysis
NMR spectroscopy
green synthesis
amides
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/159260
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-159260
record_format dspace
spelling I19-R120-10915-1592602023-10-24T20:07:41Z http://sedici.unlp.edu.ar/handle/10915/159260 Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations Corredor Montaña, Jeisson D. Loaiza, Alix E. Romanelli, Gustavo Pablo De Waele, Isabelle Tobón, Yeny A. Gómez Castaño, Jovanny A. 2021 2023-10-24T11:54:06Z en Química Density Functional Theory conformational analysis NMR spectroscopy green synthesis amides In this study, the conformational behavior of N-benzyl-N-(furan-2-ylmethyl) acetamide in chloroform was addressed by using a combined experimental/theoretical strategy using NMR spectroscopy and quantum chemical calculations. The 1H and 13C one‑dimensional NMR spectra, as well as the two-dimensional HSQC-DEPT and HMBC-DEPT NMR spectra, evinced the presence of a hindered cis(E)-trans(Z) rotational equilibrium in solution. DFT calculations were performed at different theoretical levels using the polarizable continuum model (PCM) and predicted nine (four Z and five E structures) stable conformations. The interconversion dynamics among the different confirmations were established in terms of four different rotational equilibria in CDCl3. The chemical shifts in the 1H and 13C NMR spectra of the compound are similar to the values calculated for the two most abundant conformational equilibria at room temperature, one caused by two Z rotamers and the other by two E rotamers. The compound was also characterized for the first time by FTIR, Raman spectroscopy, and GC/MS spectrometry. Additionally, several acylation methodologies for synthesizing the title compound from N-benzyl-1-(furan-2-yl)methanamine were tested which resulted in high yields (> 90%) under very convenient conditions (10 min, at room temperature). Centro de Investigación y Desarrollo en Ciencias Aplicadas Articulo Articulo http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 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
Density Functional Theory
conformational analysis
NMR spectroscopy
green synthesis
amides
spellingShingle Química
Density Functional Theory
conformational analysis
NMR spectroscopy
green synthesis
amides
Corredor Montaña, Jeisson D.
Loaiza, Alix E.
Romanelli, Gustavo Pablo
De Waele, Isabelle
Tobón, Yeny A.
Gómez Castaño, Jovanny A.
Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations
topic_facet Química
Density Functional Theory
conformational analysis
NMR spectroscopy
green synthesis
amides
description In this study, the conformational behavior of N-benzyl-N-(furan-2-ylmethyl) acetamide in chloroform was addressed by using a combined experimental/theoretical strategy using NMR spectroscopy and quantum chemical calculations. The 1H and 13C one‑dimensional NMR spectra, as well as the two-dimensional HSQC-DEPT and HMBC-DEPT NMR spectra, evinced the presence of a hindered cis(E)-trans(Z) rotational equilibrium in solution. DFT calculations were performed at different theoretical levels using the polarizable continuum model (PCM) and predicted nine (four Z and five E structures) stable conformations. The interconversion dynamics among the different confirmations were established in terms of four different rotational equilibria in CDCl3. The chemical shifts in the 1H and 13C NMR spectra of the compound are similar to the values calculated for the two most abundant conformational equilibria at room temperature, one caused by two Z rotamers and the other by two E rotamers. The compound was also characterized for the first time by FTIR, Raman spectroscopy, and GC/MS spectrometry. Additionally, several acylation methodologies for synthesizing the title compound from N-benzyl-1-(furan-2-yl)methanamine were tested which resulted in high yields (> 90%) under very convenient conditions (10 min, at room temperature).
format Articulo
Articulo
author Corredor Montaña, Jeisson D.
Loaiza, Alix E.
Romanelli, Gustavo Pablo
De Waele, Isabelle
Tobón, Yeny A.
Gómez Castaño, Jovanny A.
author_facet Corredor Montaña, Jeisson D.
Loaiza, Alix E.
Romanelli, Gustavo Pablo
De Waele, Isabelle
Tobón, Yeny A.
Gómez Castaño, Jovanny A.
author_sort Corredor Montaña, Jeisson D.
title Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations
title_short Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations
title_full Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations
title_fullStr Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations
title_full_unstemmed Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by NMR spectroscopy and DFT calculations
title_sort insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl)acetamide by nmr spectroscopy and dft calculations
publishDate 2021
url http://sedici.unlp.edu.ar/handle/10915/159260
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