Natural J coupling (NJC) analysis of the electron lone pair effect on NMR couplings: 2. The anomeric effects on 1J(C,H) couplings and its dependence on solvent

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The electronic origin of the influence of the anomeric effect (negative hyperconjugative interaction, NHI) on the Fermi contact (FC) term of 1J(C,H) couplings has been studied from a theoretical point of view at the DFT-B3LYP level. The HN=CH2 molecule was chosen as the primary model compound, in wh...

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Autor principal: Zaccari, D.G
Otros Autores: Snyder, J.P, Peralta, J.E, Taurian, O.E, Conteras, R.H, Barone, V.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2002
Acceso en línea:Registro en Scopus
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030 |a MOPHA 
100 1 |a Zaccari, D.G. 
245 1 0 |a Natural J coupling (NJC) analysis of the electron lone pair effect on NMR couplings: 2. The anomeric effects on 1J(C,H) couplings and its dependence on solvent 
260 |c 2002 
270 1 0 |m Conteras, R.H.; Departamento de Física, Universidad de Buenos Aires, Ciudad Universitaria, Pab. 1, 1428 Buenos Aires, Argentina; email: contrera@df.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Wasylishen, R., (1974) Nuclear Magnetic Resonance Spectroscopy of Nuclei Other Than Protons, p. 105. , edited by T. Axenrod and G.A. Webb (New York: Wiley-Interscience) 
504 |a Hansen, P.E., (1981) Progr. NMR. Spectrosc., 14, p. 175 
504 |a Gil, V.M.S., Von Philipsborn, W., (1989) Magn. Reson. Chem., 27, p. 409 
504 |a Wolfe, S., Pinto, B.M., Varma, V., Leung, R.Y.N., (1990) Can. J. Chem., 68, p. 1051 
504 |a Perlin, A.S., Casu, B., (1969) Tetrahedron Lett., p. 2921 
504 |a Bohlmann, F., (1957) Angew. Chem., 69, p. 641 
504 |a (1958) Chem. Ber., 91, p. 2157 
504 |a Kirby, A.J., (1983) The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, p. 1. , Berlin: Springer-Verlag 
504 |a Eliel, E.L., Allinger, N.L., Angyal, S.J., Morrison, G.A., (1965) Conformational Analysis, , New York: Wiley-Interscience 
504 |a Hehre, W.J., Radom, L., Schleyer, P.V.R., Pople, J.A., (1986) Ab initio Molecular Orbital Theory, , New York: Wiley 
504 |a Juaristi, E., (1991) Introduction to Stereochemistry and Conformational Analysis, , New York: Wiley 
504 |a Reed, A.E., Schleyer, P.V.R., (1990) J. Amer. Chem. Soc., 112, p. 1434 
504 |a Kowalewski, J., (1977) Progr. NMR Spectrosc., 11, p. 1 
504 |a Kowalewski, J., (1982) Ann. Rep. NMR Spectrosc., 12, p. 81 
504 |a Contreras, R.H., Facelli, J.C., (1993) Ann. Rep. NMR Spectrosc., 27, p. 255 
504 |a Contreras, R.H., Peralta, J.E., Giribet, C.G., Ruiz de Azúa, M.C., Facelli, J.C., (2000) Ann. Rep. NMR Spectrosc., 41, p. 55 
504 |a Contreras, R.H., Peralta, J.E., (2000) Progr. NMR Spectrosc., 37, p. 321 
504 |a Peralta, J.E., Contreras, R.H., Snyder, J.P., (2000) J. Chem. Soc. Chem. Commun., p. 2025 
504 |a Reed, A.E., Curtiss, L.A., Weinhold, F., (1988) Chem. Rev., 88, p. 899 
504 |a De Kimpe, N., Verhe, R., De Buyck, L., Schamp, N., (1984) Can. J. Chem., 62, p. 1812 
504 |a Braillon, B., Lasne, M.C., Rippoll, J.L., Denis, J.M., (1982) Nouv. J. Chim., 6, p. 121 
504 |a Becke, A.D., (1988) Phys. Rev., A, 38, p. 3098 
504 |a Lee, C., Yang, W., Parr, R.G., (1988) Phys. Rev. B, 37, p. 785 
504 |a Becke, A.D., (1993) J. Chem. Phys., 98, p. 5648 
504 |a Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian98, Revision A.7, , Pittsburgh, PA: Gaussian, Inc 
504 |a Guilleme, J., San Fabián, J., (1998) J. Chem. Phys., 109, p. 8168 
504 |a Pople, J.A., Beveridge, D.L., (1970) Approximate Molecular Orbital Theory, , New York: MCGraw-Hill 
504 |a Peralta, J.E., Ruiz de Azúa, M.C., Contreras, R.H., (2000) Theoret. Chem. Accounts, 105, p. 156 
504 |a Glendening, E.D., Reed, A.E., Carpenter, J.E., Weinhold, F., (1998) NBO Version 3.1, Included in the Gaussian98 package of programs 
504 |a Barfield, M., (1980) J. Amer. Chem. Soc., 102, p. 1 
504 |a Mertius, S., Scrocco, E., Tomasi, J., (1981) Chem. Phys., 55, 117 
504 |a Mertius, S., Tomasi, J., (1982) Chem. Phys., 65, p. 239 
504 |a Peralta, J.E., Barone, V., Ruiz de Azúa, M.C., Contreras, R.H., (2001) Molec. Phys., 99, p. 655 
504 |a Helgaker, T., Jensen, H.J.A., Jørgensen, P., Olsen, J., Ruud, K., gren, H., Andersen, T., Vahtras, O., (1997) Dalton, an electronic structure program, Release 1.0 
504 |a Cai, J., Davies, A.G., Schiesser, C.H., (1994) J. Chem. Soc. Perkin Trans., 2, p. 1151 
504 |a Juaristi, E., Cuevas, G., Vela, A., (1994) J. Amer. Chem. Soc., 116, p. 5796 
504 |a Brakta, M., Farr, R.N., Chaguir, B., Massiot, G., Lavaud, C., Anderson W.R., Jr., Sinou, D., Doyle Daves G., Jr., (1993) J. Org. Chem., 58, p. 2992 
504 |a Cuevas, G., Juaristi, E., Vela, A., (1999) J. Phys. Chem. A, 103, p. 932 
504 |a Anderson, J.E., Bloodworth, A.J., Cai, J., Davies, A.G., Tallant, N.A., (1992) J. Chem. Soc. Chem. Commun., p. 1689 
504 |a Eliel, E.L., Giza, G.A., (1968) J. Org. Chem., 33, p. 3754 
504 |a Lemeiux, R.U., Pavia, A.A., Marti, J.C., Watanabe, K.A., (1969) Can. J. Chem., 47, p. 4427 
504 |a Diz, A.C., Giribet, C.G., Ruiz de Azúa, C.C., Contreras, R.H., (1990) Intl. J. Quantum Chem., 37, p. 663 
504 |a Ruiz de Azúa, M.C., Giribet, C.G., Aucar, G.A., Lobayan de Bonczok, R., (1993) J. Molec. Struct. Theochem, 284, p. 249 
504 |a Krivdin, L.B., Zinchenko, S.V., Shcherbakov, V.V., Kalabin, G.A., Contreras, R.H., Tufró, M.F., Ruiz de Azúa, M.C., Giribet, C.G., (1989) J. Magn. Reson., 84, p. 1 
504 |a Contreras, R.H., Ruiz de Azúa, M.C., Giribet, C.G., Aucar, G.A., Lobayan de Bonczok, R., (1993) J. Molec. Struct. Theoehem, 284, p. 249 
504 |a Yonezawa, T., Morishima, I., (1968) J. Molec. Spectrosc., 27, p. 210 
504 |a Sterner, T., (1996) Crystallogr. Rev., 6, p. 1 
504 |a Desiraju, G.R., (1991) Accounts Chem. Res., 24, p. 290 
504 |a Chandrasekaran, S., Boykin, D.W., (1992) Heteroatom. Chem., 3, p. 63 
504 |a Satonaka, H., Abe, K., Hirota, M., (1987) Bull. Chem. Soc. Jap., 60, p. 953 
504 |a Satonaka, H., Abe, K., Hirota, M., (1987) Bull. Chem. Soc. Jap., 61, p. 2031 
504 |a Afonin, A.V., Andriyankov, M.A., (1988) Zh. Org. Khim., 24, p. 1034 
504 |a Afonin, A.V., Vashchenko, A.V., Takagi, T., Kimura, A., Fujiwara, H., (1999) Can. J. Chem., 77, p. 416 
504 |a Giribet, C.G., Vizioli, C.V., Ruiz de Azúa, M.C., Contreras, R.H., Dannenberg, J.J., Masunov, A., (1996) J. Chem. Soc. Faraday Trans., 92, p. 3029 
520 3 |a The electronic origin of the influence of the anomeric effect (negative hyperconjugative interaction, NHI) on the Fermi contact (FC) term of 1J(C,H) couplings has been studied from a theoretical point of view at the DFT-B3LYP level. The HN=CH2 molecule was chosen as the primary model compound, in which both FC 1J(C,H) couplings were decomposed into bond contributions with the natural J coupling dissection approach (NJC). Differences between the 1J(C,H)FC couplings for C-H bonds in synperiplanar and antiperiplanar orientations with respect to the nitrogen non-bonding electron pair closely follow the experimental trend. They are made up chiefly of three NJC contributions: 'bond', 'direct lone pair' and the 'carbon-core orbitals'. The NHI influence on these terms was studied by applying the natural bond orbital (NBO) deletion procedure to the charge transfer interaction into the antiperiplanar (C-H) antibond (n(N)→(C-H)*) prior to the NJC dissection calculation. The dielectric solvation effect on both the total FC terms and the respective NJC contributions was estimated by carrying out the calculations using the polarization continuum model. Inhibition of the anomeric effect is evident when the solvent polarity is increased. NHI saturates rapidly with increasing solvent dielectric. Specific solute-solvent interaction effects on 1J(C,H) couplings were estimated by evaluating molecular complex models of the form CH2=HN⋯S (S = H2O and DMSO).  |l eng 
536 |a Detalles de la financiación: Consejo de Investigaciones Científicas y Tecnológicas de la Provincia de Córdoba, 4649-O.P. 91/98 
536 |a Detalles de la financiación: Secretaría de Ciencia y Técnica, Universidad de Buenos Aires, TX54 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: D.G.Z., J.E.P., O.E.T., V.B. and R.H.C. gratefully acknowledge financial support from CONICET (Grant 4160), UBACYT (Grant TX54), CONICOR (Grant 4649-O.P. 91/98) and SECyT-UNRC. 
593 |a Departamento de Quimica y Fisica, FCEF-QyN, Universidad Nacional de Rio Cuarto, Rio Cuarto, Argentina 
593 |a Department of Chemistry, Emory University, Atlanta, GA 30306, United States 
593 |a Departamento de Física, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a CHARGE TRANSFER 
690 1 0 |a CHEMICAL BONDS 
690 1 0 |a DIELECTRIC MATERIALS 
690 1 0 |a ELECTRONS 
690 1 0 |a FERMI LEVEL 
690 1 0 |a MAGNETIC COUPLINGS 
690 1 0 |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 
690 1 0 |a ORGANIC SOLVENTS 
690 1 0 |a ANOMERIC EFFECTS 
690 1 0 |a MOLECULAR PHYSICS 
700 1 |a Snyder, J.P. 
700 1 |a Peralta, J.E. 
700 1 |a Taurian, O.E. 
700 1 |a Conteras, R.H. 
700 1 |a Barone, V. 
773 0 |d 2002  |g v. 100  |h pp. 705-715  |k n. 6  |p Mol. Phys.  |x 00268976  |w (AR-BaUEN)CENRE-420  |t Molecular Physics 
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856 4 0 |u https://doi.org/10.1080/00268970110091862  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00268976_v100_n6_p705_Zaccari  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00268976_v100_n6_p705_Zaccari  |y Registro en la Biblioteca Digital 
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999 |c 81349 

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