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De Kowalewski, D.G.; Díez, E.; Esteban, A.L.; Barone, V.; Peralta, J.E.; Contreras, R.H. "Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study" (2004) Magnetic Resonance in Chemistry. 42(11):938-943
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Abstract:

One- two- and three 13C, 13C (n = 1, 2, 3) scalar couplings, nJ(C,C) in a set of pyrimidine derivatives were studied both experimentally at natural abundance and theoretically by their DFT calculation of all four contributions. Trends of non-contact terms are discussed and substituent effects are rationalized, comparing some of them with the corresponding values in benzene and pyridine. Although substituent effects on non-contact terms are relatively important, the whole trend is dominated by the Fermi contact term. According to the current literature, substituent effects on 1J(C,C) couplings in benzene derivatives are dominated by the inductive effect, which, apparently, is also the case in nitrogen heteroaromatic compounds. However, some differences observed in this work for substituent effects on 1J(C,C) couplings in pyrimidine derivatives suggest that in the latter type of compounds substituent effects can be affected by the orientation of the ring nitrogen lone pairs. Copyright © 2004 John Wiley & Sons, Ltd.

Registro:

Documento: Artículo
Título:Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study
Autor:De Kowalewski, D.G.; Díez, E.; Esteban, A.L.; Barone, V.; Peralta, J.E.; Contreras, R.H.
Filiación:Departamento de Física, FCEyN, P. 1 and CONICET (C1428EHA), Buenos Aires, Argentina
Depto. de Quim. Fis. Apl., Facultad de Ciencias, C2, Univ. Autónoma de Madrid, E-28049, Madrid, Spain
Depto. de Quím. Física, Universidad de Alicante, Apartado 99, E-03080 Alicante, Spain
Department of Chemistry, Rice University, Houston, TX 77005-1892, United States
Palabras clave:13C NMR; Dual path transmission; Hyperconjugative interactions; J(C,C) scalar couplings; Lone-pair orientation effect; NMR; Pyrimidines; benzene; carbon 13; nitrogen derivative; pyridine; pyrimidine derivative; article; carbon nuclear magnetic resonance; chemical interaction; density functional theory; molecular model; substitution reaction
Año:2004
Volumen:42
Número:11
Página de inicio:938
Página de fin:943
DOI: http://dx.doi.org/10.1002/mrc.1426
Título revista:Magnetic Resonance in Chemistry
Título revista abreviado:Magn. Reson. Chem.
ISSN:07491581
CODEN:MRCHE
CAS:benzene, 71-43-2; carbon 13, 14762-74-4; pyridine, 110-86-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v42_n11_p938_DeKowalewski

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Citas:

---------- APA ----------
De Kowalewski, D.G., Díez, E., Esteban, A.L., Barone, V., Peralta, J.E. & Contreras, R.H. (2004) . Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study. Magnetic Resonance in Chemistry, 42(11), 938-943.
http://dx.doi.org/10.1002/mrc.1426
---------- CHICAGO ----------
De Kowalewski, D.G., Díez, E., Esteban, A.L., Barone, V., Peralta, J.E., Contreras, R.H. "Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study" . Magnetic Resonance in Chemistry 42, no. 11 (2004) : 938-943.
http://dx.doi.org/10.1002/mrc.1426
---------- MLA ----------
De Kowalewski, D.G., Díez, E., Esteban, A.L., Barone, V., Peralta, J.E., Contreras, R.H. "Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study" . Magnetic Resonance in Chemistry, vol. 42, no. 11, 2004, pp. 938-943.
http://dx.doi.org/10.1002/mrc.1426
---------- VANCOUVER ----------
De Kowalewski, D.G., Díez, E., Esteban, A.L., Barone, V., Peralta, J.E., Contreras, R.H. Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study. Magn. Reson. Chem. 2004;42(11):938-943.
http://dx.doi.org/10.1002/mrc.1426