NMR J(13C,13C) spin-spin coupling constants in pyridine-carboxaldehydes. Experimental and DFT-B3LYP studies

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J(13C,13C) spin-spin couplings were measured at natural abundance in five pyridine aldehyde derivatives. Such couplings were also calculated at the DFT-B3LYP-6-311G**/EPR-III level of theory where special attention was paid to their possible stereospecific behaviors. Dielectric solvent effects were...

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Detalles Bibliográficos
Autor principal: Taurian, O.E
Otros Autores: De Kowalewski, D.G, Pérez, J.E, Contreras, Rubén Horacio
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2005
Acceso en línea:Registro en Scopus
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100 1 |a Taurian, O.E. 
245 1 0 |a NMR J(13C,13C) spin-spin coupling constants in pyridine-carboxaldehydes. Experimental and DFT-B3LYP studies 
260 |c 2005 
270 1 0 |m Contreras, R.H.; Departamento de Física, FCEyN, Ciudad Universitaria, P.1, C1428EHA Buenos Aires, Argentina; email: contrera@df.uba.ar 
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504 |a De Kowalewski, D.G., Kowalewski, V.J., Peralta, J.E., Eskuche, G., Contreras, R.H., Esteban, A.L., Galache, M.P., (1999) E. Díez, Magn. Reson. Chem., 37, p. 227 
506 |2 openaire  |e Política editorial 
520 3 |a J(13C,13C) spin-spin couplings were measured at natural abundance in five pyridine aldehyde derivatives. Such couplings were also calculated at the DFT-B3LYP-6-311G**/EPR-III level of theory where special attention was paid to their possible stereospecific behaviors. Dielectric solvent effects were calculated on all four isotropic contributions to J(13C,13C) couplings using the polarization continuum model, PCM. It is observed that the inclusion of dielectric solvent effects in general leads to a better agreement between calculated and experimental couplings. 2J(13CC,13CA) couplings were observed to be sensitive to the aldehyde side-chain conformation (coupling pathway: CC-Ci-CA, where C C stands for the carbonyl-, Ci is the aromatic ipso- and CA is an adjacent aromatic-C atom). This is a positive coupling and becomes unusually large for a trans configuration between the carbonyl CO and the CC-Ci bonds. In this conformation, there is an enhancement of conjugative interactions involving the π(CO) and π(C CCi) bonding and antibonding orbitals. © 2005 Elsevier B.V. All rights reserved.  |l eng 
593 |a Departamento de Física, FCEFQyN, Universidad Nacional de Río Cuarto, Ruta Nacional No. 36, Km 601, 5800 Río Cuarto, Argentina 
593 |a Area Química-Física, Facultad de Química, Bioquímica Y Farmacia, Universidad Nacional de San Luis, Chacabuco y Pedernera, 5700 San Luis, Argentina 
593 |a Departamento de Física, FCEyN, Ciudad Universitaria, P.1, C1428EHA Buenos Aires, Argentina 
690 1 0 |a CONJUGATIVE INTERACTIONS 
690 1 0 |a GEMINAL COUPLINGS 
690 1 0 |a NEGATIVE HYPERCONJUGATIVE INTERACTIONS 
690 1 0 |a SCALAR COUPLINGS 
690 1 0 |a STEREOSPECIFICITY 
690 1 0 |a ALDEHYDES 
690 1 0 |a CARBON MONOXIDE 
690 1 0 |a CONFORMATIONS 
690 1 0 |a CONTINUUM MECHANICS 
690 1 0 |a ANTIBONDING ORBITALS 
690 1 0 |a CONJUGATIVE INTERACTIONS 
690 1 0 |a PYRIDINE ALDEHYDES 
690 1 0 |a MOLECULAR STRUCTURE 
700 1 |a De Kowalewski, D.G. 
700 1 |a Pérez, J.E. 
700 1 |a Contreras, Rubén Horacio 
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