Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling

Autores
Stortz, Carlos Arturo; Maier, Marta Silvia
Año de publicación
2000
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The conformational features of four diastereomers of the γ-lactone 2-ethyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid were investigated by calculations which included molecular mechanics (MM3), semiempirical (AM1) and ab initio molecular orbital theory (HF/6-31G), the latter including solvent emulation. Results were compared with those obtained by 1H NMR spectroscopy of natural and synthetic analogues in which a long aliphatic chain replaces the ethyl side chain. A notable agreement was found between the experimental vicinal ring coupling constants and those computed by the ab initio calculations; MM3 also gave rise to a fair agreement, while AM1 shows large failures to encounter the potential energy surface of these and other five-membered rings.
Fil: Stortz, Carlos Arturo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Maier, Marta Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Materia
Five membered rings
Conformational analysis
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:11336/138070
Acceder
id CONICETDig_2b651dd781313024c38a0638c74fea10
oai_identifier_str oai:ri.conicet.gov.ar:11336/138070
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modellingStortz, Carlos ArturoMaier, Marta SilviaFive membered ringsConformational analysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The conformational features of four diastereomers of the γ-lactone 2-ethyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid were investigated by calculations which included molecular mechanics (MM3), semiempirical (AM1) and ab initio molecular orbital theory (HF/6-31G), the latter including solvent emulation. Results were compared with those obtained by 1H NMR spectroscopy of natural and synthetic analogues in which a long aliphatic chain replaces the ethyl side chain. A notable agreement was found between the experimental vicinal ring coupling constants and those computed by the ab initio calculations; MM3 also gave rise to a fair agreement, while AM1 shows large failures to encounter the potential energy surface of these and other five-membered rings.Fil: Stortz, Carlos Arturo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Maier, Marta Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaAmerican Chemical Society2000-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documentapplication/pdfhttp://hdl.handle.net/11336/138070Stortz, Carlos Arturo; Maier, Marta Silvia; Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling; American Chemical Society; Journal Of The Chemical Society-perkin Transactions 2; 9; 8-2000; 1832-18360300-9580CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2000/P2/b003862hinfo:eu-repo/semantics/altIdentifier/doi/10.1039/b003862hinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:39:26Zoai:ri.conicet.gov.ar:11336/138070instacron: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 11:39:27.265CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
title Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
spellingShingle Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
Stortz, Carlos Arturo
Five membered rings
Conformational analysis
title_short Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
title_full Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
title_fullStr Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
title_full_unstemmed Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
title_sort Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
dc.creator.none.fl_str_mv Stortz, Carlos Arturo
Maier, Marta Silvia
author Stortz, Carlos Arturo
author_facet Stortz, Carlos Arturo
Maier, Marta Silvia
author_role author
author2 Maier, Marta Silvia
author2_role author
dc.subject.none.fl_str_mv Five membered rings
Conformational analysis
topic Five membered rings
Conformational analysis
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 conformational features of four diastereomers of the γ-lactone 2-ethyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid were investigated by calculations which included molecular mechanics (MM3), semiempirical (AM1) and ab initio molecular orbital theory (HF/6-31G), the latter including solvent emulation. Results were compared with those obtained by 1H NMR spectroscopy of natural and synthetic analogues in which a long aliphatic chain replaces the ethyl side chain. A notable agreement was found between the experimental vicinal ring coupling constants and those computed by the ab initio calculations; MM3 also gave rise to a fair agreement, while AM1 shows large failures to encounter the potential energy surface of these and other five-membered rings.
Fil: Stortz, Carlos Arturo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Maier, Marta Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
description The conformational features of four diastereomers of the γ-lactone 2-ethyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid were investigated by calculations which included molecular mechanics (MM3), semiempirical (AM1) and ab initio molecular orbital theory (HF/6-31G), the latter including solvent emulation. Results were compared with those obtained by 1H NMR spectroscopy of natural and synthetic analogues in which a long aliphatic chain replaces the ethyl side chain. A notable agreement was found between the experimental vicinal ring coupling constants and those computed by the ab initio calculations; MM3 also gave rise to a fair agreement, while AM1 shows large failures to encounter the potential energy surface of these and other five-membered rings.
publishDate 2000
dc.date.none.fl_str_mv 2000-08
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/11336/138070
Stortz, Carlos Arturo; Maier, Marta Silvia; Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling; American Chemical Society; Journal Of The Chemical Society-perkin Transactions 2; 9; 8-2000; 1832-1836
0300-9580
CONICET Digital
CONICET
url http://hdl.handle.net/11336/138070
identifier_str_mv Stortz, Carlos Arturo; Maier, Marta Silvia; Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling; American Chemical Society; Journal Of The Chemical Society-perkin Transactions 2; 9; 8-2000; 1832-1836
0300-9580
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://pubs.rsc.org/en/content/articlelanding/2000/P2/b003862h
info:eu-repo/semantics/altIdentifier/doi/10.1039/b003862h
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/vnd.openxmlformats-officedocument.wordprocessingml.document
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
_version_ 1846782058854088704
score 12.982451

Publicaciones similares