Abstract:
Proton chemical shifts for the C‐18, C‐21, CO2CH2CH3 and CO2CH2CH3 protons of epimeric ethyl esters of 20(R,S)‐hydroxy‐23‐norcholanoic acids were measured in deuteriochloroform and pyridine‐d5. The observed solvent shifts due to specific OH—pyridine hydrogen‐bonded complexes allowed the quantification of the epimeric mixtures by analysis of the pyridine‐d51H NMR spectra. The main features of the pyridine‐induced shifts are rationalized in terms of the preferred conformations for the 20R‐ and 20S‐epimers, which are predicted by molecular mechanics calculations. Copyright © 1991 John Wiley & Sons Ltd.
Registro:
Documento: |
Artículo
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Título: | 1H NMR and molecular mechanics studies of epimeric ethyl esters of 20(R, S)‐hydroxy‐23‐norcholanoic acids |
Autor: | Maier, M.S.; Seldes, A.M.; Gros, E.G. |
Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Buenos Aires, Argentina
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Palabras clave: | 1H NMR; 20(R,S)‐Hydroxy‐23‐norcholanoic acid derivatives; Molecular mechanics calculations; Pyridine‐induced shifts |
Año: | 1991
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Volumen: | 29
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Número: | 2
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Página de inicio: | 137
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Página de fin: | 142
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DOI: |
http://dx.doi.org/10.1002/mrc.1260290208 |
Título revista: | Magnetic Resonance in Chemistry
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Título revista abreviado: | Magn. Reson. Chem.
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ISSN: | 07491581
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v29_n2_p137_Maier |
Referencias:
- Seldes, A.M., Anding, C.A., Gros, E.G., (1980) Steroids, 36, p. 575
- Seldes, A.M., Gros, E.G., (1982) Steroids, 39, p. 181
- Maier, M.S., Seldes, A.M., Gros, E.G., (1985) J. Labelled Compd. Radiopharm., 22, p. 467
- Seldes, A.M., Maier, M.S., Gros, E.G., 13C NMR studies of epimeric 20(R,S)-hydroxy-23-norcholanoic acid derivatives (1986) Magnetic Resonance in Chemistry, 24, p. 239
- Bohl, M., (1987) Z. Naturforsch., Teil C, 42, p. 221
- Cooley, G., Kirk, D.N., Morgan, R.E., Melo, (1977), p. 1390. , J. Chem. Soc., Perkin Trans. 1; Nes, W.R., Varkey, T.E., (1976) J. Org. Chem., 41, p. 1652
- Johnson, C.E., Jr, Bovey, F.A., (1958) J. Chem. Phys., 29, p. 1012
- Gil, V.M.S., Murrell, J.N., (1964) Trans. Faraday Soc., 60, p. 248
- Butenandt, A., Grosse, W., Über den Ersatz der 3-ständigen Hydroxylgruppe im Pregnenolon und Androstendiol durch Chlor (1937) Berichte der deutschen chemischen Gesellschaft (A and B Series), 70, p. 1446
- ApSimon, J.W., Eenkhoorn, J.A., (1974) Can. J. Chem., 52, p. 4113
Citas:
---------- APA ----------
Maier, M.S., Seldes, A.M. & Gros, E.G.
(1991)
. 1H NMR and molecular mechanics studies of epimeric ethyl esters of 20(R, S)‐hydroxy‐23‐norcholanoic acids. Magnetic Resonance in Chemistry, 29(2), 137-142.
http://dx.doi.org/10.1002/mrc.1260290208---------- CHICAGO ----------
Maier, M.S., Seldes, A.M., Gros, E.G.
"1H NMR and molecular mechanics studies of epimeric ethyl esters of 20(R, S)‐hydroxy‐23‐norcholanoic acids"
. Magnetic Resonance in Chemistry 29, no. 2
(1991) : 137-142.
http://dx.doi.org/10.1002/mrc.1260290208---------- MLA ----------
Maier, M.S., Seldes, A.M., Gros, E.G.
"1H NMR and molecular mechanics studies of epimeric ethyl esters of 20(R, S)‐hydroxy‐23‐norcholanoic acids"
. Magnetic Resonance in Chemistry, vol. 29, no. 2, 1991, pp. 137-142.
http://dx.doi.org/10.1002/mrc.1260290208---------- VANCOUVER ----------
Maier, M.S., Seldes, A.M., Gros, E.G. 1H NMR and molecular mechanics studies of epimeric ethyl esters of 20(R, S)‐hydroxy‐23‐norcholanoic acids. Magn. Reson. Chem. 1991;29(2):137-142.
http://dx.doi.org/10.1002/mrc.1260290208