Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study

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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 ra...

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Detalles Bibliográficos
Autor principal: De Kowalewski, D.G
Otros Autores: Díez, E., Esteban, A.L, Barone, V., Peralta, J.E, Contreras, Rubén Horacio
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2004
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-10944245338 
024 7 |2 cas  |a benzene, 71-43-2; carbon 13, 14762-74-4; pyridine, 110-86-1 
030 |a MRCHE 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
100 1 |a De Kowalewski, D.G. 
245 1 0 |a Substituent effects on scalar J(13C, 13C) couplings in pyrimidines. An experimental and DFT study 
260 |c 2004 
270 1 0 |m Esteban, A.L.; Depto. de Quím. Física, Universidad de Alicante, Apartado 99, E-03080 Alicante, Spain; email: angel.esteban@ua.es 
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506 |2 openaire  |e Política editorial 
520 3 |a 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.  |l eng 
593 |a Departamento de Física, FCEyN, P. 1 and CONICET (C1428EHA), Buenos Aires, Argentina 
593 |a Depto. de Quim. Fis. Apl., Facultad de Ciencias, C2, Univ. Autónoma de Madrid, E-28049, Madrid, Spain 
593 |a Depto. de Quím. Física, Universidad de Alicante, Apartado 99, E-03080 Alicante, Spain 
593 |a Department of Chemistry, Rice University, Houston, TX 77005-1892, United States 
690 1 0 |a 13C NMR 
690 1 0 |a DUAL PATH TRANSMISSION 
690 1 0 |a HYPERCONJUGATIVE INTERACTIONS 
690 1 0 |a J(C,C) SCALAR COUPLINGS 
690 1 0 |a LONE-PAIR ORIENTATION EFFECT 
690 1 0 |a NMR 
690 1 0 |a PYRIMIDINES 
690 1 0 |a BENZENE 
690 1 0 |a CARBON 13 
690 1 0 |a NITROGEN DERIVATIVE 
690 1 0 |a PYRIDINE 
690 1 0 |a PYRIMIDINE DERIVATIVE 
690 1 0 |a ARTICLE 
690 1 0 |a CARBON NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a CHEMICAL INTERACTION 
690 1 0 |a DENSITY FUNCTIONAL THEORY 
690 1 0 |a MOLECULAR MODEL 
690 1 0 |a SUBSTITUTION REACTION 
700 1 |a Díez, E. 
700 1 |a Esteban, A.L. 
700 1 |a Barone, V. 
700 1 |a Peralta, J.E. 
700 1 |a Contreras, Rubén Horacio 
773 0 |d 2004  |g v. 42  |h pp. 938-943  |k n. 11  |p Magn. Reson. Chem.  |x 07491581  |w (AR-BaUEN)CENRE-972  |t Magnetic Resonance in Chemistry 
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