Experimental and theoretical study of substituent effects on3J(13Cl-1H) coupling constants in 1-X-bicyclo[1.1.1]pentanes
A series of 23 bridgehead-substituted bicyclo[1.1.1]pentanes were synthesized and the 3J(C1-H) coupling constants determined from their proton-coupled 13C NMR spectra. It was found that the values of the couplings are strongly dependent upon the type of substituent present, with powerful effects exe...
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1996
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| LEADER | 04452caa a22005057a 4500 | ||
|---|---|---|---|
| 001 | PAPER-18746 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250204093629.0 | ||
| 008 | 190411s1996 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0000166283 | |
| 030 | |a JPOCE | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Della, E.W. | |
| 245 | 1 | 0 | |a Experimental and theoretical study of substituent effects on3J(13Cl-1H) coupling constants in 1-X-bicyclo[1.1.1]pentanes |
| 260 | |c 1996 | ||
| 270 | 1 | 0 | |m Della, E.W.; Department of Chemistry, Flinders University, Bedford Park, SA 5042, Australia |
| 504 | |a Marchand, A.P., (1982) Methods in Stereochemical Analysis, 1. , edited by A. P. Marchand, Verlag Chemie International, Deerfield Beach, EL | ||
| 504 | |a Marshall, J.L., (1982) Methods in Stereochemieal Analysis, 1. , edited by A. P. Marchand, Verlag Chemie International, Deerfield Beach, FL | ||
| 504 | |a Krivdin, L.B., Della, E.W., (1991) Prog. Nucl. Magn. Reson. Spearosc., 23, pp. 301-610 | ||
| 504 | |a Barfield, M., (1993) J. Am. Chem. Soc., 115, pp. 6916-6928 | ||
| 504 | |a Della, E.W., Pigou, P.E., Taylor, D.K., Krisdin, L.B., Contreras, R.H., (1993) Aust. J Chem., 46, pp. 63-72 | ||
| 504 | |a Aucar, G.A., Zunino, V., Ferraro, M.B., Giribet, C.G., Ruiz De Azúa, M.C., Contreras, R.H., (1990) J. Mol. Struct. (Theochem), 205, pp. 63-77 | ||
| 504 | |a Barfield, M., (1980) J. Am. Chem. Soc., 102, pp. 1-7 | ||
| 504 | |a Engelmann, A.R., Contreras, R.H., (1983) Int. J. Quantum Chem., 23, pp. 1033-1045 | ||
| 504 | |a Natiello, M.A., Contreras, R.H., (1984) Chem Phys. Lett., 104, pp. 568-571 | ||
| 504 | |a Engelmann, A.R., Natiello, M.A., Scuseria, G.E., Contreras, R.H., (1986) Comput. Phys. Commun., 39, pp. 409-420 | ||
| 504 | |a Scuseria, G.E., Facelli, J.C., Contreras, R.H., Engelmann, A.R., (1983) Chem. Phys. Lett., 96, pp. 560-562 | ||
| 504 | |a Contreras, R.H., Scuseria, G.E., (1984) Org. Magn. Reson., 22, pp. 411-414 | ||
| 504 | |a Aucar, G.A., Ruiz De Azúa, M.C., Giribet, C.G., Contreras, R.H., (1990) J. Mol. Struct. (Theochem), 205, pp. 79-88 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a A series of 23 bridgehead-substituted bicyclo[1.1.1]pentanes were synthesized and the 3J(C1-H) coupling constants determined from their proton-coupled 13C NMR spectra. It was found that the values of the couplings are strongly dependent upon the type of substituent present, with powerful effects exerted by the halogens in particular. The IPPP-CLOPPA-INDO theoretical approach, which was employed to provide a measure of the extent of through-bond versus through-space transmission of coupling information, was found to give 3J(C1-H) values in good agreement with experimental data. Empirical substituent parameter regressions were performed and found to be consistent with the CLOPPA description of the increase in both the through-bond and through-space contributions to the coupling. The substituent parameter regressional analyses also demonstrated that electronegativity effects play a predominant role in determining the magnitude of the couplings, particularly in those substrates in which the substituent is attached to the ring system by a second-row element. © 1996 by John Wiley & Sons, Ltd. |l eng | |
| 593 | |a Department of Chemistry, Flinders University, Bedford Park, SA 5042, Australia | ||
| 593 | |a Facultad de Ciendas Exactas y Naturales y Agrimensura, UNNE, 3400 Corrientes, Argentina | ||
| 593 | |a Departmento de Física, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 1, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a Lochert, I.J. | |
| 700 | 1 | |a Peruchena, N.M. | |
| 700 | 1 | |a Aucar, G.A. | |
| 700 | 1 | |a Contreras, Rubén Horacio | |
| 773 | 0 | |d 1996 |g v. 9 |h pp. 168-178 |k n. 3 |p J Phys Org Chem |x 08943230 |w (AR-BaUEN)CENRE-576 |t Journal of Physical Organic Chemistry | |
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| 961 | |a paper_08943230_v9_n3_p168_Della |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||