Artículos de revistas
The Use Of Am1 In Structural Analyses Of Primary And Secondary Enaminones
Registro en:
Journal Of Molecular Structure: Theochem. , v. 207, n. 3-4, p. 143 - 156, 1990.
1661280
10.1016/0166-1280(90)85019-J
2-s2.0-0039757948
Autor
Eberlin M.N.
Takahata Y.
Kascheres C.
Institución
Resumen
The AM1 semiempirical method was employed to study the structural features of some primary and secondary acyclic and cyclic enaminones. This method was shown to be very suitable for these compounds, enabling the correct prediction of the more stable tautomer and geometric forms and other features such as strength of intramolecular hydrogen bonds and rotational barriers. In comparison, its predecessor, the MNDO method, very often gave incorrect or inconsistent results. © 1990. 207 3-4 143 156 Greenhill, Enaminones (1977) Chemical Society Reviews, 6 Granik, Advances in the Chemistry of Enamines (1984) Russian Chemical Reviews, 53, p. 383 Eberlin, Kascheres, (1988) J. Org. Chem., 53, p. 2084 Dewar, Zoebisch, Healy, Stewart, (1985) J. Am. Chem. Soc., 107, p. 3902 Boyd, Smith, Stewart, Wimmer, Numerical sensitivity of trajectories across conformational energy hypersurfaces from geometry optimized molecular orbital calculations: AM1, MNDO, and MINDO/3 (1988) Journal of Computational Chemistry, 9, p. 387 Buemi, Zuccarello, Raudino, (1988) J. Mol. Struct. (Theochem), 164, p. 379 Galera, Lluch, Oliva, Bertrán, (1988) J. Mol. Struct. (Theochem), 163, p. 101 Masamura, (1988) J. Mol. Struct. (Theochem), 299, p. 1649 Higgins, Thomson, A theoretical study of the rotational isomers of nitrosomethanol by semiempirical (AM1) andab initio methods (1988) Journal of Computational Chemistry, 9, p. 212 Fabian, AM1 calculations of rotation around essential single bonds and preferred conformations in conjugated molecules (1988) Journal of Computational Chemistry, 9, p. 369 Marcos, Maraver, Chiara, Gómez-Sánchez, MNDO/H and AM1 studies of nitro enamines with intramolecular hydrogen bonds (1988) Journal of the Chemical Society, Perkin Transactions 2, p. 2059 Dewar, Program No. 506 (1986) QCPE Bull., , Research Group Grob, Wilkens, Die Enonamin-Enolimin-Tautomerie (1967) Helvetica Chimica Acta, 50, p. 725 Greenhill, Determination of the tautomeric ratio in certain enaminones (1969) Journal of the Chemical Society B: Physical Organic, p. 299 Dudek, Holm, (1962) J. Am. Chem. Soc., 84, p. 2691 Dudek, Volpp, Nuclear Magnetic Resonance Studies of Keto-Enol Equilibria. V. Isomerization in Aliphatic Schiff Bases (1963) Journal of the American Chemical Society, 85, p. 2697 Dudek, Dudek, Spectroscopic Studies of Keto-Enol Equilibria. VII. Nitrogen-15 Substituted Schiff Bases (1964) Journal of the American Chemical Society, 86, p. 4238 Dabrowski, (1963) Spectrochim. Acta, 19, p. 475 Weinstein, Wyman, (1958) J. Org. Chem., 23, p. 1618 Collman, Alive, Sohar, Synthesis and Infrared Study of Some Rhodium Coördination Compounds1 (1958) Journal of the American Chemical Society, 80, p. 1100 Dudek, (1965) J. Org. Chem., 30, p. 548 Brown, Nonhebel, (1968) Tetrahedron, 24, p. 5655 Célérier, Lhommet, (1982) J. Heterocycl. Chem., 19, p. 481 Morris, Tallman, Gordon, (1976) J. Mol. Struct., 34, p. 263 Smith, Taylor, (1976) Spectrochim. Acta, Part A, 32, p. 1477 Kashima, Aoyama, Yamamoto, Nishio, Yamada, Nuclear magnetic resonance spectral study of ?-aminoenones (1975) Journal of the Chemical Society, Perkin Transactions 2, p. 665 Gómez-Sánchez, Aldave, Scheidegger, Proton magnetic resonance spectra of N-substituted 3-aminocrotonic esters (1968) Journal of the Chemical Society C: Organic, p. 2570 Gómez-Sánchez, Valle, Bellanato, Infrared and nuclear magnetic resonance absorption and isomerism of 3-aminocrotonic esters. Part II. (1973) Journal of the Chemical Society, Perkin Transactions 2, p. 15 Kozerski, von Philipsborn, 15N chemical shifts as a conformational probe in enaminones A variable temperature study at natural isotope abundance (1981) Organic Magnetic Resonance, 17, p. 301 Dabrowski, Kamienska-Trela, Electronic spectra of .alpha.,.beta.-unsaturated carbonyl compounds. I. An evaluation of increments characteristic of changes in configuration (cis/trans) and conformation (s-cis/s-trans) based on direct observation of the isomerization of enamino aldehydes and ketones (1976) Journal of the American Chemical Society, 98, p. 2826 Ostercamp, (1970) J. Org. Chem., 35, p. 1632 Kozerski, Kamienska-Trela, Kania, von Philipsborn, 15N-NMR study of activated enamines. Structural dependence of ? (15N) andnJ(N,H) in primary, secondary and tertiary enamino-ketones, esters and amides (1983) Helvetica Chimica Acta, 66, p. 2113 Dudek, Volpp, Nuclear Magnetic Resonance Studies of Keto-Enol Equilibria. V. Isomerization in Aliphatic Schiff Bases (1963) Journal of the American Chemical Society, 85, p. 2697 Allinger, Cava, De Jongh, Johnson, Lebel, Stevens, (1976) Organic Chemistry, , Worth Publishers, New York Pople, Gordon, (1967) J. Am. Chem. Soc., 89, p. 4253