Artículo
Rae, I.D.; Weigold, J.A.; De Kowalewski, D.G.; Biekofsky, R.R.; Contreras, R.H. "Relative signs of three-bond fluorine-carbon and four-bond fluorine-hydrogen couplings in 2-substituted fluorobenzenes" (1996) Magnetic Resonance in Chemistry. 34(3):181-184
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Abstract:
In a series of 2-X-fluorobenzenes, the relative signs between 3J(CF) and the corresponding 4J(HF) couplings were determined. In most cases like signs were found. However, for the coupling pathway involving the X group, unlike signs were found for X = CN, NCS and NO2. For other electronegative substituents, 4J(H3F) couplings were found to have too small a magnitude to permit determination of their signs with respect to 3J(C3F). No adequate correlation between the algebraic values of 3J(C3F) couplings and the electronegativity of the substituent placed at ring position 2 was found. Some speculative arguments are advanced in order to rationalize the observed trend.
Registro:
| Documento: | Artículo |
| Título: | Relative signs of three-bond fluorine-carbon and four-bond fluorine-hydrogen couplings in 2-substituted fluorobenzenes |
| Autor: | Rae, I.D.; Weigold, J.A.; De Kowalewski, D.G.; Biekofsky, R.R.; Contreras, R.H. |
| Filiación: | Victoria University of Technology, P.O. Box 14428 MCMC, Melbourne, Vic. 8001, Australia Department of Chemistry, Monash University, Clayton, Vic. 3168, Australia Departamento de Fisica, Fac. de Ciencias Exactas y Naturales, Pabellón 1, 1428 Buenos Aires, Argentina |
| Palabras clave: | Carbon-fluorine coupling; Hydrogen-fluorine coupling; Relative signs |
| Año: | 1996 |
| Volumen: | 34 |
| Número: | 3 |
| Página de inicio: | 181 |
| Página de fin: | 184 |
| DOI: | http://dx.doi.org/10.1002/(SICI)1097-458X(199603)34:3<181::AID-OMR853>3.0.CO;2-S |
| Título revista: | Magnetic Resonance in Chemistry |
| Título revista abreviado: | Magn. Reson. Chem. |
| ISSN: | 07491581 |
| CODEN: | MRCHE |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v34_n3_p181_Rae |
Referencias:
- Weigert, F.J., Roberts, J.D., (1971) J. Am. Chem Soc., 93, p. 2361
- Wray, V., Lincoln, D.N., (1975) J. Magn. Reson, 18, p. 374
- Lichter, R.L., Wasylishen, R.E., (1975) J. Am. Chem. Soc., 97, p. 1808
- Doddrell, D., Barfield, M., Adcock, W., Aurangzeb, M., Jordan, D., (1976) J. Chem. Soc., Perkin Trans. 2, 402
- Ernst, L., Lincoln, D.N., Wray, V., (1976) J. Magn. Reson, 21, p. 115
- Spear, R.J., Forsyth, D.A., Olah, G.A., (1976) J. Am. Chem. Soc., 98, p. 2493
- Wray, V., Ernst, L., Lustig, E., (1977) J. Magn. Reson., 27, p. 1
- Manatt, S.L., Cooper, M.A., (1977) J. Am. Chem Soc., 99, p. 4561
- Wray, V., (1978) J. Chem. Soc., Perkin Trans. 2, 855
- Natiello, M.A., Contreras, R.H., (1984) Chem. Phys. Lett., 104, p. 568
- Contreras, R.H., Facelli, J.C., (1993) Annu. Rep. NMR Spectrosc., 27, p. 255
- Engelmann, A.R., Natiello, M.A., Scuseria, G.E., Contreras, R.H., (1986) Comput. Phys. Commun., 39, p. 409
- Dewar, M.J.S., Stewart, J.J.P., (1986) AMPAC, Program No. 527, Quantum Chemistry Program Exchange, 527. , University of Indiana, Bloomington, IN
- Aucar, G.A., Contreras, R.H., (1991) J. Magn. Reson., 93, p. 413
- Dewar, M.J.S., Thiel, W., (1977) J. Am. Chem. Soc., 99, p. 4989
- Scuseria, G.E., Engelmann, A.R., Contreras, R.H., (1982) Theor. Chim. Acta, 61, p. 49
- Bax, A., Morris, G.A., (1981) J. Magn. Reson., 42, p. 501
- Rae, I.D., Weigold, J.A., Contreras, R.H., Yamamoto, G., (1992) Magn. Reson. Chem., 30, p. 1047
- Cholli, A.L., (1981) J. Magn. Reson., 42, p. 501. , and references cited therein
- Gutowsky, H.S., Holm, C.H., Saika, A., Williams, G.A., (1957) J. Am. Chem. Soc., 79, p. 4596
- Diehl, P., Gränacher, I., (1961) J. Chem. Phys., 34, p. 1846
- Patterson, W.G., Spedding, H., (1963) Can. J. Chem., 41, p. 2706
- Evans, D.F., (1963) Mol. Phys., 6, p. 179
- Lustig, E., Diehl, P., (1966) J. Chem. Phys., 44, p. 2974
- Barbier, C., Faucher, H., Gagnaire, D., Rousseau, A., (1966) J. Chem. Phys., 63, p. 283
- Hansen, P.E., Berg, A., Jacobsen, H.J., Manzara, A.P., Michl, J.U., (1977) Org. Magn. Reson., 10, p. 179
- Loemker, J.E., Read J.M., Jr., Goldstein, J.H., (1968) J. Phys. Chem., 72, p. 991
- Freeman, R., (1965) J. Chem. Phys., 43, p. 3087
- Loemker, J.E., Pryse, K.M., Read J.M., Jr., Goldstein, J.H., (1969) Can. J. Chem., 47, p. 209
- Barfield, M., Karplus, M., (1967) J. Am. Chem. Soc., 91, p. 1
- Wray, V., (1981) J. Am. Chem. Soc., 103, p. 2503
- Holland, H.L., (1978) Tetrahedron Lett., p. 881
- Holland, H.L., Thomas, E.M., (1979) Can. J. Chem., 57, p. 3069
- Hickey, J.P., Butler, I.S., Pouskouleli, G., (1980) J. Magn. Reson., 38, p. 501
- Kowalewski, J., (1982) Annu. Rep. NMR Spectrosc., 12, p. 81
- Engelmann, A.R., Scuseria, G.E., Contreras, R.H., (1982) J. Magn. Reson., 50, p. 21
- Natiello, M.A., Scuseria, G.E., Contreras, R.H., (1983) J. Mol. Struct. Theochem, 105, p. 233
- Jokisaari, J., Kuonanoja, J., Pulkkinen, A., Väänänen, T., (1981) Mol. Phys., 44, p. 197
- Lounila, J., Jokisaari, J., (1982) Prog. NMR Spectrosc., 15, p. 201
- Väänänen, T., Jokisaari, J., Lounila, J., (1982) J. Magn. Reson., 49, p. 73
Citas:
---------- APA ----------
Rae, I.D., Weigold, J.A., De Kowalewski, D.G., Biekofsky, R.R. & Contreras, R.H. (1996) . Relative signs of three-bond fluorine-carbon and four-bond fluorine-hydrogen couplings in 2-substituted fluorobenzenes. Magnetic Resonance in Chemistry, 34(3), 181-184.http://dx.doi.org/10.1002/(SICI)1097-458X(199603)34:3<181::AID-OMR853>3.0.CO;2-S
---------- CHICAGO ----------
Rae, I.D., Weigold, J.A., De Kowalewski, D.G., Biekofsky, R.R., Contreras, R.H. "Relative signs of three-bond fluorine-carbon and four-bond fluorine-hydrogen couplings in 2-substituted fluorobenzenes" . Magnetic Resonance in Chemistry 34, no. 3 (1996) : 181-184.http://dx.doi.org/10.1002/(SICI)1097-458X(199603)34:3<181::AID-OMR853>3.0.CO;2-S
---------- MLA ----------
Rae, I.D., Weigold, J.A., De Kowalewski, D.G., Biekofsky, R.R., Contreras, R.H. "Relative signs of three-bond fluorine-carbon and four-bond fluorine-hydrogen couplings in 2-substituted fluorobenzenes" . Magnetic Resonance in Chemistry, vol. 34, no. 3, 1996, pp. 181-184.http://dx.doi.org/10.1002/(SICI)1097-458X(199603)34:3<181::AID-OMR853>3.0.CO;2-S
---------- VANCOUVER ----------
Rae, I.D., Weigold, J.A., De Kowalewski, D.G., Biekofsky, R.R., Contreras, R.H. Relative signs of three-bond fluorine-carbon and four-bond fluorine-hydrogen couplings in 2-substituted fluorobenzenes. Magn. Reson. Chem. 1996;34(3):181-184.http://dx.doi.org/10.1002/(SICI)1097-458X(199603)34:3<181::AID-OMR853>3.0.CO;2-S
