Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies

Autores
Iguchi, Daniela; Ravelli, Davide; Erra Balsells, Rosa; Bonesi, Sergio Mauricio
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The attribution of 1H and 13C NMR signals of a library of 5-, 6- and 7-substituted 2,2-dimethylchroman-4-one derivatives is reported. Substituent effects were interpreted in terms of the Hammett equation, showing a good correlation for carbons para- to the substituent group, not for the meta- ones. Similarly, the Lynch correlation shows the additivity of the substituent chemical shifts in the case of both H and C nuclei, again with the exception of the carbons in the meta- position. Density Functional Theory (DFT)-predicted 1H and 13C chemical shifts correspond closely with experimentally observed values, with some exceptions for C NMR data; however, the correlation is valid only for the aromatic moiety and cannot be extended to the heterocyclic ring of the chroman-4-one scaffold.
Fil: Iguchi, Daniela. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ravelli, Davide. Universita degli Studi di Pavia; Italia
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
DENSITY FUNCTIONAL CALCULATIONS
HAMMETT CORRELATION
LYNCH CORRELATION
NMR SPECTROSCOPY
OXYGEN HETEROCYCLES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/170650
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studiesIguchi, DanielaRavelli, DavideErra Balsells, RosaBonesi, Sergio MauricioDENSITY FUNCTIONAL CALCULATIONSHAMMETT CORRELATIONLYNCH CORRELATIONNMR SPECTROSCOPYOXYGEN HETEROCYCLEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The attribution of 1H and 13C NMR signals of a library of 5-, 6- and 7-substituted 2,2-dimethylchroman-4-one derivatives is reported. Substituent effects were interpreted in terms of the Hammett equation, showing a good correlation for carbons para- to the substituent group, not for the meta- ones. Similarly, the Lynch correlation shows the additivity of the substituent chemical shifts in the case of both H and C nuclei, again with the exception of the carbons in the meta- position. Density Functional Theory (DFT)-predicted 1H and 13C chemical shifts correspond closely with experimentally observed values, with some exceptions for C NMR data; however, the correlation is valid only for the aromatic moiety and cannot be extended to the heterocyclic ring of the chroman-4-one scaffold.Fil: Iguchi, Daniela. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Ravelli, Davide. Universita degli Studi di Pavia; ItaliaFil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaMolecular Diversity Preservation International2020-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/170650Iguchi, Daniela; Ravelli, Davide; Erra Balsells, Rosa; Bonesi, Sergio Mauricio; Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies; Molecular Diversity Preservation International; Molecules; 25; 9; 4-2020; 2061-20741420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/25/9/2061info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules25092061info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:10:08Zoai:ri.conicet.gov.ar:11336/170650instacron: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:34982025-10-22 11:10:09.227CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
title Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
spellingShingle Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
Iguchi, Daniela
DENSITY FUNCTIONAL CALCULATIONS
HAMMETT CORRELATION
LYNCH CORRELATION
NMR SPECTROSCOPY
OXYGEN HETEROCYCLES
title_short Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
title_full Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
title_fullStr Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
title_full_unstemmed Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
title_sort Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies
dc.creator.none.fl_str_mv Iguchi, Daniela
Ravelli, Davide
Erra Balsells, Rosa
Bonesi, Sergio Mauricio
author Iguchi, Daniela
author_facet Iguchi, Daniela
Ravelli, Davide
Erra Balsells, Rosa
Bonesi, Sergio Mauricio
author_role author
author2 Ravelli, Davide
Erra Balsells, Rosa
Bonesi, Sergio Mauricio
author2_role author
author
author
dc.subject.none.fl_str_mv DENSITY FUNCTIONAL CALCULATIONS
HAMMETT CORRELATION
LYNCH CORRELATION
NMR SPECTROSCOPY
OXYGEN HETEROCYCLES
topic DENSITY FUNCTIONAL CALCULATIONS
HAMMETT CORRELATION
LYNCH CORRELATION
NMR SPECTROSCOPY
OXYGEN HETEROCYCLES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The attribution of 1H and 13C NMR signals of a library of 5-, 6- and 7-substituted 2,2-dimethylchroman-4-one derivatives is reported. Substituent effects were interpreted in terms of the Hammett equation, showing a good correlation for carbons para- to the substituent group, not for the meta- ones. Similarly, the Lynch correlation shows the additivity of the substituent chemical shifts in the case of both H and C nuclei, again with the exception of the carbons in the meta- position. Density Functional Theory (DFT)-predicted 1H and 13C chemical shifts correspond closely with experimentally observed values, with some exceptions for C NMR data; however, the correlation is valid only for the aromatic moiety and cannot be extended to the heterocyclic ring of the chroman-4-one scaffold.
Fil: Iguchi, Daniela. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ravelli, Davide. Universita degli Studi di Pavia; Italia
Fil: Erra Balsells, Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
description The attribution of 1H and 13C NMR signals of a library of 5-, 6- and 7-substituted 2,2-dimethylchroman-4-one derivatives is reported. Substituent effects were interpreted in terms of the Hammett equation, showing a good correlation for carbons para- to the substituent group, not for the meta- ones. Similarly, the Lynch correlation shows the additivity of the substituent chemical shifts in the case of both H and C nuclei, again with the exception of the carbons in the meta- position. Density Functional Theory (DFT)-predicted 1H and 13C chemical shifts correspond closely with experimentally observed values, with some exceptions for C NMR data; however, the correlation is valid only for the aromatic moiety and cannot be extended to the heterocyclic ring of the chroman-4-one scaffold.
publishDate 2020
dc.date.none.fl_str_mv 2020-04
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/11336/170650
Iguchi, Daniela; Ravelli, Davide; Erra Balsells, Rosa; Bonesi, Sergio Mauricio; Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies; Molecular Diversity Preservation International; Molecules; 25; 9; 4-2020; 2061-2074
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/170650
identifier_str_mv Iguchi, Daniela; Ravelli, Davide; Erra Balsells, Rosa; Bonesi, Sergio Mauricio; Substituent effects on NMR spectroscopy of 2,2-dimethylchroman-4-one derivatives: Experimental and theoretical studies; Molecular Diversity Preservation International; Molecules; 25; 9; 4-2020; 2061-2074
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/25/9/2061
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules25092061
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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 12.982451

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