Abstract
Cationic heteroconjugation equilibria of more than ninety systems consisting of substituted pyridines, their N-oxides, and trimethylamine N-oxide, i. e., in systems with “mixed” hydrogen bridges of type OHN+ (NHO+) were studied in propylene carbonate. Both experimental systems without proton transfer, BH+/B1, and those with proton transfer, B1H+/B, were explored. The stability of the “mixed” hydrogen bridges, OHN+ (NHO+), is compared with that of the OHC+-type bridges. The influence of the difference in basicity of the conjugate base of the proton donor and the proton acceptor on the presence of the proton transfer equilibria, and, consequently, the possibility of determination of the cationic heteroconjugation constant values is discussed.
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REFERENCES
J. F. Coetzee, Progr. Org. Chem. 4, 45 (1967).
L. Chmurzyński, Solvent Effect on Acidic--Basic Interactions of Pyridine N-Oxide Derivatives (University of Gdańsk, Gdańsk, 1994).
L. Chmurzyński, E. Kaczmarczyk, and A. Liwo, Anal. Chim. Act 338, 261 (1997).
L. Chmurzyński, E. Kaczmarczyk, D. Augustin-Nowacka, and P. Barczyński, Anal. Chim. Acta 336, 107 (1996).
L. Chmurzyński, E. Kaczmarczyk, M. Nesterowicz, G. Wawrzyniak, and Z. Warnke, Aust. J. Chem. 49, 931 (1996).
J. Barthel, R. Wachter, and H. H. Gores, Modern Aspects of Electrochemisty, Vol. 13, (Plenum, New York, 1979).
A. Wawrzynów, E. Kaczmarczyk, and L. Chmurzyński, J. Mol. Struct., in press.
T. Fujinaga and K. Izutsu, Pure Appl. Chem. 27, 275 (1971).
K. Izutsu, I. M. Kolthoff, T. Fujinaga, M. Hattori, and M. K. Chantooni Jr, Anal. Chem. 49, 503 (1977).
A. Wawrzynów, Ph.D. Thesis, University of Gdańsk, Gdańsk, 1985.
L. Chmurzyński, A. Wawrzynów, and Z. Pawlak, Electrochim. Acta 35, 665 (1990).
L. Chmurzyński, J. Solution Chem. 21, 171 (1992).
L Chmurzyński A. Wawrzynów, and Z. Pawlak, J. Chem. Soc. Faraday Trans. I 12, 4269 (1989).
L. Chmurzyński, and Z. Warnke, Aust. J. Chem. 46, 185 (1993).
J. Kostrowicki and A. Liwo, Comput. Chem. 8, 91, 101 (1984).
J. Kostrowicki and A. Liwo, Comput. Chem. 11, 195 (1987).
J. Kostrowicki and A. Liwo, Talanta 37, 645 (1990).
A. Wawrzynów and L. Chmurzyński, J. Chem. Thermodyn., (in press).
M. Jaskólski, M. Gdaniec, Z. Kosturkiewicz, and M. Szafraʼn Pol. J. Chem. 52, 2399 (1978).
I. Olovson and P. G. Jonsson, in The Hydrogen Bond, P. Schuster, G. Zundel, and C. Sandorfy, eds., Vol. II, (Elsevier, Amsterdam, 1976), p. 393.
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Wawrzynów, A., Liwo, A., Kaczmarczyk, E. et al. Cationic Heteroconjugation Constants in the OHN+ and NHO+ Systems in Propylene Carbonate: Dependence on Difference in Basicity. Journal of Solution Chemistry 27, 463–472 (1998). https://doi.org/10.1023/A:1022656722697
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DOI: https://doi.org/10.1023/A:1022656722697