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Abstract:

In this work, several features of the polar bond-polarizable bond interaction are studied using an experimental and theoretical methodology. The NMR 13C chemical shifts for 1-CN,2-OCH3-naphthalene, 1-CHO,2-OCH3-naphthalene and 5-Cl,6-OCH3,8-NH2-quinoline were measured. In these three compounds, steric interactions force the methoxy group to be oriented cis to the adjacent C-C bond with the smaller π mobile bond order. GIAO DFT-B3LYP/6-311G** magnetic shielding calculations were performed on such compounds, on their corresponding monosubstituted analogs, and on model systems that intend to mimic the electrostatic response of a naphthalene substrate to a polar group. Effects of σ electron delocalization interactions on the methoxy 13C chemical shift are studied separately using the NBO approach. Failure of the level of theory employed to describe some 13C chemical shifts in the chlorine-containing compound are rationalized in terms of contributions from the spin orbit interaction. The model compounds studied in this work shed light on the influence of the double bond character on the PB-PzB interaction. Aromatic 13C chemical shifts were proven to be sensitive probes to measure such interaction, which can be thought of as the π electrostatic response to a proximate polar moiety, causing a shielding effect on the carbon atom nearest to the positive end of the polar group. © 2000 Elsevier Science B.V.

Registro:

Documento: Artículo
Título:The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study
Autor:Contreras, R.H.; Taurian, O.E.; Ortiz, F.S.; Peralta, J.E.
Filiación:Departamento De Física, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, Pabellón 1, (1428), Buenos Aires, Argentina
Departamento De Química Y Física, Facultad De Ciencias Exactas, Universidad Nacional De Río Cuarto, R8, Km 601 (5800), Río Cuarto, Argentina
Palabras clave:Chemical shifts; Electrostatic response; Intramolecular interactions; Methoxy group; NMR; carbon; chemical compound; chlorine; methoxynaphthalene; methyl group; naphthalene derivative; quinoline derivative; unclassified drug; article; calculation; chemical binding; chemical interaction; chemical structure; electricity; electron; magnetism; molecular physics; polarization; proton nuclear magnetic resonance; stereochemistry
Año:2000
Volumen:556
Número:1-3
Página de inicio:263
Página de fin:273
DOI: http://dx.doi.org/10.1016/S0022-2860(00)00642-6
Título revista:Journal of Molecular Structure
Título revista abreviado:J. Mol. Struct.
ISSN:00222860
CODEN:JMOSB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v556_n1-3_p263_Contreras

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Citas:

---------- APA ----------
Contreras, R.H., Taurian, O.E., Ortiz, F.S. & Peralta, J.E. (2000) . The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study. Journal of Molecular Structure, 556(1-3), 263-273.
http://dx.doi.org/10.1016/S0022-2860(00)00642-6
---------- CHICAGO ----------
Contreras, R.H., Taurian, O.E., Ortiz, F.S., Peralta, J.E. "The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study" . Journal of Molecular Structure 556, no. 1-3 (2000) : 263-273.
http://dx.doi.org/10.1016/S0022-2860(00)00642-6
---------- MLA ----------
Contreras, R.H., Taurian, O.E., Ortiz, F.S., Peralta, J.E. "The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study" . Journal of Molecular Structure, vol. 556, no. 1-3, 2000, pp. 263-273.
http://dx.doi.org/10.1016/S0022-2860(00)00642-6
---------- VANCOUVER ----------
Contreras, R.H., Taurian, O.E., Ortiz, F.S., Peralta, J.E. The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study. J. Mol. Struct. 2000;556(1-3):263-273.
http://dx.doi.org/10.1016/S0022-2860(00)00642-6