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

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 e...

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Autores principales: Stortz, C.A., Maier, M.S.
Formato: JOUR
Materias:
Carboxylic acids
Conformations
Interfacial energy
Molecular dynamics
Nuclear magnetic resonance spectroscopy
Diastereomeric lactones
Molecular orbital
Esters
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_03009580_v_n9_p1832_Stortz
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_03009580_v_n9_p1832_Stortz
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spelling todo:paper_03009580_v_n9_p1832_Stortz2023-10-03T15:18:07Z Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling Stortz, C.A. Maier, M.S. Carboxylic acids Conformations Interfacial energy Molecular dynamics Nuclear magnetic resonance spectroscopy Diastereomeric lactones Molecular orbital Esters 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_03009580_v_n9_p1832_Stortz
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Carboxylic acids
Conformations
Interfacial energy
Molecular dynamics
Nuclear magnetic resonance spectroscopy
Diastereomeric lactones
Molecular orbital
Esters
spellingShingle Carboxylic acids
Conformations
Interfacial energy
Molecular dynamics
Nuclear magnetic resonance spectroscopy
Diastereomeric lactones
Molecular orbital
Esters
Stortz, C.A.
Maier, M.S.
Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
topic_facet Carboxylic acids
Conformations
Interfacial energy
Molecular dynamics
Nuclear magnetic resonance spectroscopy
Diastereomeric lactones
Molecular orbital
Esters
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.
format JOUR
author Stortz, C.A.
Maier, M.S.
author_facet Stortz, C.A.
Maier, M.S.
author_sort Stortz, C.A.
title Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
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
url http://hdl.handle.net/20.500.12110/paper_03009580_v_n9_p1832_Stortz
work_keys_str_mv AT stortzca configurationalassignmentsofdiastereomericglactonesusingvicinalhhnmrcouplingconstantsandmolecularmodelling
AT maierms configurationalassignmentsofdiastereomericglactonesusingvicinalhhnmrcouplingconstantsandmolecularmodelling
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