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Abstract:

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.

Registro:

Documento: Artículo
Título:Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling
Autor:Stortz, C.A.; Maier, M.S.
Filiación:Departamento de Quimica Organica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:Carboxylic acids; Conformations; Interfacial energy; Molecular dynamics; Nuclear magnetic resonance spectroscopy; Diastereomeric lactones; Molecular orbital; Esters
Año:2000
Número:9
Página de inicio:1832
Página de fin:1836
Título revista:Journal of the Chemical Society. Perkin Transactions 2
Título revista abreviado:J Chem Soc Perkin Trans 2
ISSN:03009580
CODEN:JCPKB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n9_p1832_Stortz

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Citas:

---------- APA ----------
Stortz, C.A. & Maier, M.S. (2000) . Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling. Journal of the Chemical Society. Perkin Transactions 2(9), 1832-1836.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n9_p1832_Stortz [ ]
---------- CHICAGO ----------
Stortz, C.A., Maier, M.S. "Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling" . Journal of the Chemical Society. Perkin Transactions 2, no. 9 (2000) : 1832-1836.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n9_p1832_Stortz [ ]
---------- MLA ----------
Stortz, C.A., Maier, M.S. "Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling" . Journal of the Chemical Society. Perkin Transactions 2, no. 9, 2000, pp. 1832-1836.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n9_p1832_Stortz [ ]
---------- VANCOUVER ----------
Stortz, C.A., Maier, M.S. Configurational assignments of diastereomeric γ-lactones using vicinal H-H NMR coupling constants and molecular modelling. J Chem Soc Perkin Trans 2. 2000(9):1832-1836.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n9_p1832_Stortz [ ]