The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study

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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, ster...

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Detalles Bibliográficos
Autor principal: Contreras, Rubén Horacio
Otros Autores: Taurian, O.E, Ortiz, F.S, Peralta, J.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2000
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100 1 |a Contreras, Rubén Horacio 
245 1 4 |a The polar bond-polarizable bond interaction in 1-X,2-methoxy naphthalenes. An experimental and theoretical study 
260 |c 2000 
270 1 0 |m Contreras, R.H.; Departamento de Física, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: contrera@df.uba.ar 
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506 |2 openaire  |e Política editorial 
520 3 |a 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.  |l eng 
536 |a Detalles de la financiación: Consejo de Investigaciones Científicas y Tecnológicas de la Provincia de Córdoba 
536 |a Detalles de la financiación: Secretaria de Ciencia y Tecnica, Universidad de Buenos Aires 
536 |a Detalles de la financiación: Universidad Nacional de Río Cuarto 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 00604 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, UBACyT 
536 |a Detalles de la financiación: Financial support form CONICOR, SECyT (UNRC), CONICET, UBACyT and ANPCyT (PICT 00604) are gratefully acknowledged. 
593 |a Departamento De Física, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, Pabellón 1, (1428), Buenos Aires, Argentina 
593 |a Departamento De Química Y Física, Facultad De Ciencias Exactas, Universidad Nacional De Río Cuarto, R8, Km 601 (5800), Río Cuarto, Argentina 
650 1 7 |2 spines  |a CARBON 
690 1 0 |a CHEMICAL SHIFTS 
690 1 0 |a ELECTROSTATIC RESPONSE 
690 1 0 |a INTRAMOLECULAR INTERACTIONS 
690 1 0 |a METHOXY GROUP 
690 1 0 |a NMR 
690 1 0 |a CHEMICAL COMPOUND 
690 1 0 |a CHLORINE 
690 1 0 |a METHOXYNAPHTHALENE 
690 1 0 |a METHYL GROUP 
690 1 0 |a NAPHTHALENE DERIVATIVE 
690 1 0 |a QUINOLINE DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ARTICLE 
690 1 0 |a CALCULATION 
690 1 0 |a CHEMICAL BINDING 
690 1 0 |a CHEMICAL INTERACTION 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a ELECTRICITY 
690 1 0 |a ELECTRON 
690 1 0 |a MAGNETISM 
690 1 0 |a MOLECULAR PHYSICS 
690 1 0 |a POLARIZATION 
690 1 0 |a PROTON NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a STEREOCHEMISTRY 
700 1 |a Taurian, O.E. 
700 1 |a Ortiz, F.S. 
700 1 |a Peralta, J.E. 
773 0 |d 2000  |g v. 556  |h pp. 263-273  |k n. 1-3  |p J. Mol. Struct.  |x 00222860  |w (AR-BaUEN)CENRE-222  |t Journal of Molecular Structure 
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