Artículo
Sproviero, E.M.; Ferrara, A.; Contreras, R.H.; Burton, G. "1H-1H Long range couplings in fused cyclopropanes. NMR spectral assignment and conformation of 17,18-cyclosteroids" (1996) Journal of the Chemical Society. Perkin Transactions 2. 5:933-938
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Abstract:
1H-1H NMR couplings through four bonds ( 4JH-H) involving cyclopropane hydrogens were calculated for model compounds by semiempirical methods and used for the 13C and 1H NMR spectral assignment of 17,18-cyclosteroids. The couplings (4JHH) between cyclopropyl and non-cyclopropyl hydrogens follow an angular dependence which resembles that of allylic couplings. Solution conformations of rings C-D and the side-chain of 17,18-cyclopregnanes were determined from semiempirical molecular orbital calculations, three and four bond 1H-1H coupling constants and NOE measurements.
Registro:
| Documento: | Artículo |
| Título: | 1H-1H Long range couplings in fused cyclopropanes. NMR spectral assignment and conformation of 17,18-cyclosteroids |
| Autor: | Sproviero, E.M.; Ferrara, A.; Contreras, R.H.; Burton, G. |
| Filiación: | Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, (1428) Buenos Aires, Argentina Departamento de Física, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, (1428) Buenos Aires, Argentina |
| Año: | 1996 |
| Volumen: | 5 |
| Página de inicio: | 933 |
| Página de fin: | 938 |
| DOI: | http://dx.doi.org/10.1039/P29960000933 |
| 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_v5_n_p933_Sproviero |
Referencias:
- Nickisch, K., Bittler, D., Laurent, H., Losert, W., Casals-Stenzel, J., Nishino, Y., Schillinger, E., Wiechert, R., (1987) J. Med. Chem., 30, p. 1403
- Schering, A.-G., (1968) Chem. Abstr., 69, p. 27645. , UK Pat., 1967, 1095958
- (1991) Therapeutic Drugs, 1. , S. C. Dollery, ed., Churchill Livingstone, Edinburgh
- De Meijere, A., (1979) Angew. Chem., Int. Ed. Engl., 18, p. 809
- Galli, C., (1989) Magn. Reson. Chem., 27, p. 214
- Desai, U.R., Trivedi, G.K., (1991) Magn. Reson. Chem., 29, p. 148
- Koole, L.H., Neidle, S., Crawford, M.D., Krayevski, A.A., Gurskaya, G.V., Sandström, A., Wu, J.-C., Chattopadhyaya, J., (1991) J. Org. Chem., 56, p. 6884
- Kirk, D.N., Rajagopalan, M.S., (1976) J. Chem. Soc., Perkin Trans. 1, p. 1064
- Blumbach, J., Hammond, D.A., Whitting, D.A., (1986) J. Chem. Soc., Perkin Trans. 1, p. 261
- Ferrara, A., Benedetti, M.O.V., Ghini, A.A., Burton, G., (1993) J. Chem. Res. (S), p. 276
- Haasnoot, C.A.G., De Leeuw, F.A.A.M., Altona, C., (1980) Tetrahedron, 36, p. 2783
- Diz, A.C., Giribet, C.G., Ruiz De Azúa, M.C., Contreras, R.H., (1990) Int. J. Quantum Chem., 37, p. 663
- Aucar, G.A., Contreras, R.H., (1991) J. Magn. Reson., 93, p. 413
- Aucar, G.A., unpublished work; Marat, K., Templeton, J.F., Ling, Y., Lin, W., Gupta, R.K., (1995) Magn. Reson. Chem., 33, p. 529
- Wong, T.C., Guo, W., Bohl, M., Hübner, M., Luck, G., Steiger, T., Reck, G., (1988) J. Chem. Soc., Perkin Trans. 2, p. 765
- Desai, U.R., Trivedi, G.K., (1991) J. Org. Chem., 56, p. 4625
- Lautens, M., Delanghe, P.H.M., (1995) J. Org. Chem., 60, p. 2474
- Biekofsky, R.R., Pomilio, A.B., Aristegui, R.A., Contreras, R.H., (1995) J. Mol. Struct., 344, p. 143
- Musher, J.I., (1963) Mol. Phys., 6, p. 93
- Laszlo, P., Von Ragué Schleyer, P., (1964) J. Am. Chem. Soc., 86, p. 1171
- Subramanian, P.M., Emerson, M.T., Bel, N.A., (1965) J. Org. Chem., 30, p. 2624
- Marchand, A.P., Marchand, N.W., Segre, A.L., (1969) Tetrahedron Lett., 59, p. 5207
- Cavasotto, C.N., Giribet, C.G., Ruiz De Azúa, M.C., Contreras, R.H., (1991) J. Comput. Chem., 12, p. 141
- Oddershede, J., (1978) Adv. Quantum Chem., 11, p. 275
- Pople, J.A., Beveridge, D.L., (1970) Approximate Molecular Orbital Theory, , McGraw-Hill, New York
- Bax, A., Freeman, R., (1981) J. Magn. Reson., 44, p. 542
- Garbisch, E.W., (1964) J. Am. Chem. Soc., 86, p. 5561
Citas:
---------- APA ----------
Sproviero, E.M., Ferrara, A., Contreras, R.H. & Burton, G. (1996) . 1H-1H Long range couplings in fused cyclopropanes. NMR spectral assignment and conformation of 17,18-cyclosteroids. Journal of the Chemical Society. Perkin Transactions 2, 5, 933-938.http://dx.doi.org/10.1039/P29960000933
---------- CHICAGO ----------
Sproviero, E.M., Ferrara, A., Contreras, R.H., Burton, G. "1H-1H Long range couplings in fused cyclopropanes. NMR spectral assignment and conformation of 17,18-cyclosteroids" . Journal of the Chemical Society. Perkin Transactions 2 5 (1996) : 933-938.http://dx.doi.org/10.1039/P29960000933
---------- MLA ----------
Sproviero, E.M., Ferrara, A., Contreras, R.H., Burton, G. "1H-1H Long range couplings in fused cyclopropanes. NMR spectral assignment and conformation of 17,18-cyclosteroids" . Journal of the Chemical Society. Perkin Transactions 2, vol. 5, 1996, pp. 933-938.http://dx.doi.org/10.1039/P29960000933
---------- VANCOUVER ----------
Sproviero, E.M., Ferrara, A., Contreras, R.H., Burton, G. 1H-1H Long range couplings in fused cyclopropanes. NMR spectral assignment and conformation of 17,18-cyclosteroids. J Chem Soc Perkin Trans 2. 1996;5:933-938.http://dx.doi.org/10.1039/P29960000933
