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

Autores
Corredor Montaña, Jeisson D.; Loaiza, Alix; Romanelli, Gustavo Pablo; de Waele, Isabelle; Tobón Correa, Yeny Alexandra; Gomez Castaño, Jovanny Arles
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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).
Fil: Corredor Montaña, Jeisson D.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Loaiza, Alix. Pontificia Universidad Javeriana; Colombia
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: de Waele, Isabelle. University Of Lille.; Francia
Fil: Tobón Correa, Yeny Alexandra. University Of Lille.; Francia
Fil: Gomez Castaño, Jovanny Arles. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Materia
AMIDES
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY
GREEN SYNTHESIS
NMR SPECTROSCOPY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/172440
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/172440
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculationsCorredor Montaña, Jeisson D.Loaiza, AlixRomanelli, Gustavo Pablode Waele, IsabelleTobón Correa, Yeny AlexandraGomez Castaño, Jovanny ArlesAMIDESCONFORMATIONAL ANALYSISDENSITY FUNCTIONAL THEORYGREEN SYNTHESISNMR SPECTROSCOPYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In 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).Fil: Corredor Montaña, Jeisson D.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Loaiza, Alix. Pontificia Universidad Javeriana; ColombiaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: de Waele, Isabelle. University Of Lille.; FranciaFil: Tobón Correa, Yeny Alexandra. University Of Lille.; FranciaFil: Gomez Castaño, Jovanny Arles. Universidad Pedagógica y Tecnológica de Colombia; ColombiaSociedade Brasileira de Química2020-09-21info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/172440Corredor Montaña, Jeisson D.; Loaiza, Alix; Romanelli, Gustavo Pablo; de Waele, Isabelle; Tobón Correa, Yeny Alexandra; et al.; Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculations; Sociedade Brasileira de Química; Química Nova; 44; 1; 21-9-2020; 1-140100-40421678-7064CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://quimicanova.sbq.org.br/audiencia_pdf.asp?aid2=9192&nomeArquivo=AR2020-0077.pdfinfo:eu-repo/semantics/altIdentifier/doi/10.21577/0100-4042.20170639info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:32:38Zoai:ri.conicet.gov.ar:11336/172440instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:32:38.732CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculations
title Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculations
spellingShingle Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculations
Corredor Montaña, Jeisson D.
AMIDES
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY
GREEN SYNTHESIS
NMR SPECTROSCOPY
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
dc.creator.none.fl_str_mv Corredor Montaña, Jeisson D.
Loaiza, Alix
Romanelli, Gustavo Pablo
de Waele, Isabelle
Tobón Correa, Yeny Alexandra
Gomez Castaño, Jovanny Arles
author Corredor Montaña, Jeisson D.
author_facet Corredor Montaña, Jeisson D.
Loaiza, Alix
Romanelli, Gustavo Pablo
de Waele, Isabelle
Tobón Correa, Yeny Alexandra
Gomez Castaño, Jovanny Arles
author_role author
author2 Loaiza, Alix
Romanelli, Gustavo Pablo
de Waele, Isabelle
Tobón Correa, Yeny Alexandra
Gomez Castaño, Jovanny Arles
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv AMIDES
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY
GREEN SYNTHESIS
NMR SPECTROSCOPY
topic AMIDES
CONFORMATIONAL ANALYSIS
DENSITY FUNCTIONAL THEORY
GREEN SYNTHESIS
NMR SPECTROSCOPY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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).
Fil: Corredor Montaña, Jeisson D.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Loaiza, Alix. Pontificia Universidad Javeriana; Colombia
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: de Waele, Isabelle. University Of Lille.; Francia
Fil: Tobón Correa, Yeny Alexandra. University Of Lille.; Francia
Fil: Gomez Castaño, Jovanny Arles. Universidad Pedagógica y Tecnológica de Colombia; Colombia
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).
publishDate 2020
dc.date.none.fl_str_mv 2020-09-21
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/172440
Corredor Montaña, Jeisson D.; Loaiza, Alix; Romanelli, Gustavo Pablo; de Waele, Isabelle; Tobón Correa, Yeny Alexandra; et al.; Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculations; Sociedade Brasileira de Química; Química Nova; 44; 1; 21-9-2020; 1-14
0100-4042
1678-7064
CONICET Digital
CONICET
url http://hdl.handle.net/11336/172440
identifier_str_mv Corredor Montaña, Jeisson D.; Loaiza, Alix; Romanelli, Gustavo Pablo; de Waele, Isabelle; Tobón Correa, Yeny Alexandra; et al.; Insight into the conformational space of n-benzyl-n-(furan-2-ylmethyl) acetamide by NMR spectroscopy and DFT calculations; Sociedade Brasileira de Química; Química Nova; 44; 1; 21-9-2020; 1-14
0100-4042
1678-7064
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://quimicanova.sbq.org.br/audiencia_pdf.asp?aid2=9192&nomeArquivo=AR2020-0077.pdf
info:eu-repo/semantics/altIdentifier/doi/10.21577/0100-4042.20170639
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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