Hydrogen-bond basicity of secondary and tertiary amides, carbamates, ureas and lactams
作者： Jean-Yves Le Questel , Christian Laurence , Abdeljalil Lachkar , Maryvonne Helbert , Michel Berthelot
DOI: 10.1039/P29920002091
关键词:
摘要: The hydrogen-bond basicity scale pKHB(logarithm of the formation constant 4-fluorophenol–base complexes in CCl4) has been measured for tertiary and secondary amides, carbonates, ureas lactams. hydrogen-bonding fixation site is carbonyl group, even very hindered amide ButCON(C6H11)2. In amides R1CONR2R3 decreased more by bulky R1 substituents on carbon than R2 R3 nitrogen. field effect X operates effectively resonance XCONMe2 series. increased six-membered cyclisation.
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sci-hub.se 参考文章(8)
Michael H. Abraham, Priscilla L. Grellier, David V. Prior, Robert W. Taft, Jeffrey J. Morris, Peter J. Taylor, Christian. Laurence, Michel. Berthelot, Ruth M. Doherty, . et al., A general treatment of hydrogen bond complexation constants in tetrachloromethane Journal of the American Chemical Society. ,vol. 110, pp. 8534- 8536 ,(1988) , 10.1021/JA00233A034
O. Exner, The non-additive substituent effects of two substituents adjacent to the reaction centre Collection of Czechoslovak Chemical Communications. ,vol. 41, pp. 1516- 1540 ,(1976) , 10.1135/CCCC19761516
K. Platteborze, J. Parmentier, Th. Zeegers-Huyskens, Infrared Study of the Interaction Between Carbamates and Proton Donors Spectroscopy Letters. ,vol. 24, pp. 635- 652 ,(1991) , 10.1080/00387019108018145
James E. Huheey, Carlos A. L. Filgueiras, Electronegativity, hybridization, and properties of the carbonyl group. I. Lewis basicity Journal of Organic Chemistry. ,vol. 41, pp. 49- 53 ,(1976) , 10.1021/JO00863A011
Thor Gramstad, Willy Johannes Fuglevik, A. Salmenperä, A. Block-Bolten, J. M. Toguri, H. Flood, Studies of Hydrogen Bonding. Part V. The Intermolecular Hydrogen Bond Association of Amides with Phenol and Pentachlorophenol. Acta Chemica Scandinavica. ,vol. 16, pp. 1369- 1377 ,(1962) , 10.3891/ACTA.CHEM.SCAND.16-1369
Thor Gramstad, Willy J. Fuglevik, Studies of hydrogen bonding—XIII. Hydrogen bonding ability of lactones and lactams Spectrochimica Acta. ,vol. 21, pp. 343- 344 ,(1965) , 10.1016/0371-1951(65)80015-7
Georges Guiheneuf, José-Luis M. Abboud, Abdeljalil Lachkar, L'azote, site basique des amides encombrées? Canadian Journal of Chemistry. ,vol. 66, pp. 1032- 1035 ,(1988) , 10.1139/V88-171
Christian Laurence, Michel Berthelot, Maryvonne Helbert, Khadija Sraidi, The first measurement of the hydrogen bond basicity of monomeric water, phenols and weakly basic alcohols The Journal of Physical Chemistry. ,vol. 93, pp. 3799- 3802 ,(1989) , 10.1021/J100346A083