13C- and 1H-NMR spectra of 2-pyridone derivatives
13C- and 1H-NMR spectroscopy was used to obtain njHH, nJCH and δC-13 for a series of substituted 2-hydroxypyridines (3-hydroxy; 4-hydroxy; 5-chloro; 3-methyl-5-chloro; 6-chloro; 6-amino; 6-hydroxy). It is shown that the additivity of δC-13 and 1JCH values provides a valuable criterion for differenti...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
1989
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 08797caa a22008777a 4500 | ||
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| 001 | PAPER-686 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250204094933.0 | ||
| 008 | 190411s1989 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0009150809 | |
| 030 | |a JMOSB | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a De Kowalewski, D.G. | |
| 245 | 1 | 0 | |a 13C- and 1H-NMR spectra of 2-pyridone derivatives |
| 260 | |c 1989 | ||
| 270 | 1 | 0 | |m De Kowalewski, D.G.; Depto. de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina |
| 504 | |a Brügel, (1962) Elektrochem. Ber. Bunsenges, 66, p. 159 | ||
| 504 | |a Kowalewski, de Kowalewski, Proton Magnetic Resonance Spectra of 3-Pyridines: The Unsymmetrical Four-Spin ABXY and ABKL Systems (1962) The Journal of Chemical Physics, 36, p. 266 | ||
| 504 | |a Retcofsky, Friedel, (1967) J. Phys. Chem., 71, p. 3592 | ||
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| 504 | |a Contreras, de Kowalewski, (1973) J. Mol. Struct., 16, p. 451 | ||
| 504 | |a Contreras, de Kowalewski, (1974) J. Mol. Struct., 23, p. 209 | ||
| 504 | |a Vögeli, Philipsborn, 13C and1H NMR spectroscopic studies on the structure of N-methyl-3-pyridone and 3-hydroxypyridine (1973) Organic Magnetic Resonance, 5, p. 551 | ||
| 504 | |a Zanger, Simmons, (1974) Anal. Chem., 46, p. 2042 | ||
| 504 | |a Hansen, Jakobsen, (1973) J. Magn. Res., 10, p. 74 | ||
| 504 | |a Takeuchi, Dennis, Long-range carbon-13-proton coupling constants. I. Cyanopyridines (1974) Journal of the American Chemical Society, 86, p. 3657 | ||
| 504 | |a Takeuchi, Long range13C1H coupling constants. III—methylpyridines (1975) Organic Magnetic Resonance, 7, p. 181 | ||
| 504 | |a Takeuchi, Dennis, Long range13C1H coupling constants IV—methoxy-, amino- and hydroxypyridines (1975) Organic Magnetic Resonance, 7, p. 244 | ||
| 504 | |a Vitorge, Chenon, Coupry, Lumbroso-Bader, Proton and carbon-13 nuclear magnetic resonance studies of substituted pyridines and pyrimidines: VII—The structure of hydroxy- and mercapto- pyridines and pyrimides fromJ(HH) andJ(CH) values (1983) Organic Magnetic Resonance, 21, p. 20 | ||
| 504 | |a Bauer, Hirsch, The Chemistry of Pyridine. V. Ring Substitution of Picoline and Methylpyrazine N-Oxides by Mercaptans1,2 (1965) The Journal of Organic Chemistry, 31, p. 1210 | ||
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| 504 | |a Rattet, Goldstein, Substituent effects on magnetic non- equivalence in acetals (1969) Organic Magnetic Resonance, 1, p. 229 | ||
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| 504 | |a Deady, Harrison, Topson, Proximity effects in pyridines. Proton chemical shifts in substituted methyl pyridinecarboxylates (1975) Organic Magnetic Resonance, 7, p. 41 | ||
| 504 | |a Schanek, Dereppe, Van Meerssche, (1983) Bull. Soc. Chim. Belg., 92, p. 199 | ||
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| 504 | |a Stefaniak, (1976) Tetrahedron, 32, p. 1065 | ||
| 504 | |a Fayet, Vertut, Cativiela, Melendez, Elguero, Bull. Soc. Chim. France (1984) Bull. Soc. Chim. France, p. 233 | ||
| 504 | |a Penfield, The electron distribution in crystalline α-pyridone (1953) Acta Crystallographica, 6, p. 591 | ||
| 504 | |a Oswalden, Roberts, Nuclear magnetic resonance specroscopy. Proton spectra of 2-pyridones (1971) The Journal of Organic Chemistry, 36, p. 3792 | ||
| 504 | |a Vögeli, (1970) Org. Magn. Res., 8, p. 21 | ||
| 504 | |a Beak, (1977) Acc. Chem. Res., 10, p. 186 | ||
| 504 | |a Katritzky, Lagowski, (1963) Adv. Heterocycl. Chem., 1, p. 2 | ||
| 504 | |a Albert, (1968) Heterocyclic Chemistry, , Athlone Press, London | ||
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| 504 | |a Kuzuyo, Noguchi, Okudo, Quantum chemical consideration of substituent effects on tautomeric properties of 2-pyridones-2-pyridinols. (1984) Bulletin of the Chemical Society of Japan, 57, p. 3454 | ||
| 504 | |a Simchen, Reaktionen mit Halogenwasserstoffaddukten der Nitrile, IV Zur Struktur von 6-Chlor-pyridonen-(2) (1970) Chemische Berichte, 103, p. 398 | ||
| 504 | |a Takeuchi, Aoki, The additivity of substituent effects in one-bond 13C?1H coupling constants in polysubstituted pyridines (1979) Journal of the Chemical Society, Perkin Transactions 2, p. 285 | ||
| 504 | |a Kowalewski, (1969) J. Mol. Spectrosc., 30, p. 531 | ||
| 504 | |a Contreras, Facelli, de Kowalewski, A proton NMR analysis of the OCH3 group conformation in 2-methoxypyridines (1982) Organic Magnetic Resonance, 20, p. 40 | ||
| 504 | |a Bother-By, Castellano, (1966) LAOCOON 3, , Mellon Institute, Pittsburgh, PA | ||
| 504 | |a Levy, Cargoli, (1972) J. Magn. Res., 6, p. 143 | ||
| 504 | |a D.G. de Kowalewski, R.H. Contreras and C. de los Santos, in press and references therein; D.G. de Kowalewski, and C. de los Santos, J. Mol. Struct., to be publish; Kitagawa, Mizukami, Hirai, Equilibrium studies of 5-substituted 4-hydroxy-2-methylpyrimidines. IV. Lactim-lactam tautomerism in methanol, n-butanol and n-hexane. (1978) CHEMICAL & PHARMACEUTICAL BULLETIN, 26, p. 1403 | ||
| 504 | |a Ernst, Wray, Chertkov, Sergeyev, (1977) J. Magn. Reson., 25, p. 123. , and references cited therein | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a 13C- and 1H-NMR spectroscopy was used to obtain njHH, nJCH and δC-13 for a series of substituted 2-hydroxypyridines (3-hydroxy; 4-hydroxy; 5-chloro; 3-methyl-5-chloro; 6-chloro; 6-amino; 6-hydroxy). It is shown that the additivity of δC-13 and 1JCH values provides a valuable criterion for differentiating between quinoidal and aromatic structures and in defining conformations. The first conclusion is based on the fact that for 3-substituted compounds there is accordance between experimental values and the additivity 1JCH and δC-13 values calculated for 2-pyridone. In the 6-substituted compounds there is marked deviation from additivity in 1JCH. On the other hand, it seems that the substituent effect on δC-13 in the hypothetical 2-hydroxypyridine and the real 2-pyridone are markedly different for C6, since there is no accordance between additivity and experimental values for the chemical shifts of this carbon. These conclusions are in agreement with results obtained from IR and pK studies and quantum-chemical calculations which indicate that a substituent in position 3 favours a pyridone structure, while a pyridinol structure is favoured when the substituent is at ring-position 6. © 1989. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: National Council for Scientific Research | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Grants from the Argentine National Research Council (CONICET) are gratefully acknowledged.W e thank Prof. Dr. B. Frydmann (Facultad de Far-macia y Bioquimica, Universidad de Buenos Aires) who kindly allowed us to use the 20-MHz NMR spectrograph. | ||
| 593 | |a Depto. de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina | ||
| 593 | |a Lab. de Fitoquímica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a Contreras, Rubén Horacio | |
| 700 | 1 | |a De Los Santos, C. | |
| 773 | 0 | |d 1989 |g v. 213 |h pp. 201-212 |k n. C |p J. Mol. Struct. |x 00222860 |w (AR-BaUEN)CENRE-222 |t Journal of Molecular Structure | |
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