NMR 3J(C1,H3) couplings in 1-X-bicyclo[1.1.1]pentanes. FPT-DFT and NBO studies of hyperconjugative interactions and heavy atom substituent effects
In this work a rationalization of the very large substituent effects on 3J(C1,H3) couplings in 1-X-bicyclo[1.1.1]pentanes is presented. The Fermi contact contribution to such couplings was calculated in a series of 13 X-derivatives within the DFT-B3LYP framework using the finite perturbation theory....
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2001
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 04255caa a22005297a 4500 | ||
|---|---|---|---|
| 001 | PAPER-1919 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250204092618.0 | ||
| 008 | 190411s2001 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0035889785 | |
| 030 | |a JCCHD | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Barone, V. | |
| 245 | 1 | 0 | |a NMR 3J(C1,H3) couplings in 1-X-bicyclo[1.1.1]pentanes. FPT-DFT and NBO studies of hyperconjugative interactions and heavy atom substituent effects |
| 260 | |c 2001 | ||
| 270 | 1 | 0 | |m Contreras, R.H.; Departamento de Física, Ciudad Universitaria, Universidad de Buenos Aires, Pabellón 1, 1428 Buenos Aires, Argentina; email: contrera@df.uba.ar |
| 504 | |a Karplus, M., (1959) J Chem Phys, 30, p. 11 | ||
| 504 | |a Karplus, M., (1960) J Phys Chem, 64, p. 1793 | ||
| 504 | |a Karplus, M., (1963) J Am Chem Soc, 85, p. 2870 | ||
| 504 | |a Thomas, W.A., (1997) Prog NMR Spectrosc, 30, p. 183 | ||
| 504 | |a San-Fabián, J., Guilleme, J., Díez, E., Lazzeretti, P., Malagoli, M., Zanasi, R., Esteban, A.L., Mora, F., (1994) Mol Phys, 82, p. 913 | ||
| 504 | |a Guilleme, J., San-Fabián, J., Díez, E., (1997) Mol Phys, 91, p. 243 | ||
| 504 | |a San-Fabián, J., Guilleme, J., Díez, E., (1995) An Ouím, 91, p. 200 | ||
| 504 | |a Barfield, M., Smith, W.B., (1992) J Am Chem Soc, 114, p. 1574 | ||
| 504 | |a Smith, W.B., Barfield, M., (1993) Magn Reson Chem, 31, p. 696 | ||
| 504 | |a Van Wijk, J., Huckriede, B.D., Ippel, J.H., Altona, C., (1992) Methods Enzymol, 211, p. 286 | ||
| 504 | |a Ióhr, F., Schmidt, J.M., Rüterjans, H., (1999) J Biomol NMR, 14, p. 1 | ||
| 504 | |a Contreras, R.H., Peralta, J.E., Giribet, C.G., Ruiz De Azüa, M.C., Facelli, J.C., (2000) Ann Reps NMR Spectrosc, 41, p. 55 | ||
| 504 | |a Contreras, R.H., Peralta, J.E., (2000) Prog NMR Spectrosc, 37, p. 321 | ||
| 504 | |a Hansen, P.E., (1981) Prog NMR Spectrosc, 14, p. 175 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a In this work a rationalization of the very large substituent effects on 3J(C1,H3) couplings in 1-X-bicyclo[1.1.1]pentanes is presented. The Fermi contact contribution to such couplings was calculated in a series of 13 X-derivatives within the DFT-B3LYP framework using the finite perturbation theory. Core electrons for atoms beyond the Second Row were taken into account using effective core potentials. Calculated couplings are in very good agreement with experimental values. The role played by hyperconjugative interactions involving bonds or antibonds belonging to the coupling pathway are studied using the NBO approach. Heavy atom contribution to substituent effects on 3J(C1,H3) couplings was estimated as small. This contrasts notably with trends observed in the corresponding 13C substituent chemical shifts, SCSs. The latter were estimated comparing for X = Cl, Br, I, SnMe3, calculated SCSs with their experimental values. Such estimations are in line with explicit calculations of the spin-orbit contribution reported in the literature for smaller compounds. © 2001 John Wiley & Sons, Inc. J Comput Chem. |l eng | |
| 593 | |a Departamento de Física, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 1, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a DFT |
| 690 | 1 | 0 | |a FERMI CONTACT |
| 690 | 1 | 0 | |a HEAVY ATOM EFFECT |
| 690 | 1 | 0 | |a HYPERCONJUGATIVE INTERACTIONS |
| 690 | 1 | 0 | |a NBO |
| 700 | 1 | |a Peralta, J.E. | |
| 700 | 1 | |a Contreras, Rubén Horacio | |
| 773 | 0 | |d 2001 |g v. 22 |h pp. 1615-1621 |k n. 14 |p J. Comput. Chem. |x 01928651 |w (AR-BaUEN)CENRE-323 |t Journal of Computational Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1002/jcc.1117 |x doi |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_01928651_v22_n14_p1615_Barone |x handle |y Handle |
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| 961 | |a paper_01928651_v22_n14_p1615_Barone |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||