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Abstract:

The well-known N lone-pair orientation effect on 1JCC spin-spin coupling constants (SSCCs) in oximes and their derivatives was used to study how negative hyperconjugative interactions of type LP1(O) → σ*CC depend on ortho interactions involving the OH group. This study demanded the following analyses: (i) a qualitative estimation of how 1JCC SSCCs are affected by hyperconjugative interactions, (ii) a study of similar stereochemical effects to those in oximes, but in 1JCC and 1JC1C6 in a series of 2-substituted phenols, and (iii) a quantitative estimation, with the natural bond order approach, of some key electron derealization interactions. A few unexpected results are quoted. LP1(O) → σ* CC interactions are affected by proximity interactions as follows: (a) they are enhanced by hydrogen bonds transferring charge into the (O-H)* antibonding orbital; (b) they are enhanced by proximity interactions of type LP1(O)⋯H-C; (c) they are inhibited by interactions of type LP(O1)⋯H-O. Consequences of these observations are discussed. © 2007 American Chemical Society.

Registro:

Documento: Artículo
Título:Lone-pair orientation effect of an α-oxygen atom on 1JCC NMR spin-spin coupling constants in o-substituted phenols. Experimental and DFT study
Autor:Taurian, O.E.; Contreras, R.H.; De Kowalewski, D.G.; Pérez, J.E.; Tormena, C.F.
Filiación:Department of Physics, FCEFQyN, National University of Río Cuarto, Ruta Nacional No. 36, Km 601, 5800 Río Cuarto, Argentina
Physical Chemistry Section, School of Chemistry, Biochemistry and Pharmacy, National University of San Luis, Chacabuco and Pedernera, 5700 San Luis, Argentina
Department of Physics, University of Buenos Aires and CONICET, Ciudad Universitaria, (C1428EHA) Buenos Aires, Argentina
Chemistry Institute, State University of Campinas, CP 6154, CEP: 13084-971, Campinas, SP, Brazil
Año:2007
Volumen:3
Número:4
Página de inicio:1284
Página de fin:1294
DOI: http://dx.doi.org/10.1021/ct7000396
Título revista:Journal of Chemical Theory and Computation
Título revista abreviado:J. Chem. Theory Comput.
ISSN:15499618
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15499618_v3_n4_p1284_Taurian

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Citas:

---------- APA ----------
Taurian, O.E., Contreras, R.H., De Kowalewski, D.G., Pérez, J.E. & Tormena, C.F. (2007) . Lone-pair orientation effect of an α-oxygen atom on 1JCC NMR spin-spin coupling constants in o-substituted phenols. Experimental and DFT study. Journal of Chemical Theory and Computation, 3(4), 1284-1294.
http://dx.doi.org/10.1021/ct7000396
---------- CHICAGO ----------
Taurian, O.E., Contreras, R.H., De Kowalewski, D.G., Pérez, J.E., Tormena, C.F. "Lone-pair orientation effect of an α-oxygen atom on 1JCC NMR spin-spin coupling constants in o-substituted phenols. Experimental and DFT study" . Journal of Chemical Theory and Computation 3, no. 4 (2007) : 1284-1294.
http://dx.doi.org/10.1021/ct7000396
---------- MLA ----------
Taurian, O.E., Contreras, R.H., De Kowalewski, D.G., Pérez, J.E., Tormena, C.F. "Lone-pair orientation effect of an α-oxygen atom on 1JCC NMR spin-spin coupling constants in o-substituted phenols. Experimental and DFT study" . Journal of Chemical Theory and Computation, vol. 3, no. 4, 2007, pp. 1284-1294.
http://dx.doi.org/10.1021/ct7000396
---------- VANCOUVER ----------
Taurian, O.E., Contreras, R.H., De Kowalewski, D.G., Pérez, J.E., Tormena, C.F. Lone-pair orientation effect of an α-oxygen atom on 1JCC NMR spin-spin coupling constants in o-substituted phenols. Experimental and DFT study. J. Chem. Theory Comput. 2007;3(4):1284-1294.
http://dx.doi.org/10.1021/ct7000396