Homoconjugation of Some Organic Bases in Acetonitrile

• Autorzy: Stańczyk-Dunaj M. , Jarczewski A.
• Języki publikacji: EN

Abstrakty

EN

The largest value of the homoconjugation constant in acetonitrile has been found for tribenzylamine KHOMO = 7.73 and the lower for N-methylpiperidine KHOMO = 3.44. For triethylamine, tri-n-propylamine, tributylamine, 1,3-diphenylguanidine, 2-tert-butyl- 1,1',3,3'-tetramethylguanidine, 1,1',2,2',3-pentamethylguanidine, 1,8-bis(dimethylamino) naphthalene, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene bases no homoconjugated complexes BH+B were formed. Additionally the basicity of tribenzylamine pKa = 16.13, 1,3-diphenylguanidine pKa = 18.79, 1,1',2,2',3-pentamethylguanidine pKa = 23.12, and 2-tert-butyl-1,1',3,3'-tetramethylguanidine pKa = 23.56 in acetonitrile are given.

Słowa kluczowe

EN

organic bases; basicity; pKa; homoconjugation constant; acetonitrile solvent

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 6
• Strony: 1025--1032
• Opis fizyczny: Bibliogr. 25 poz., rys.

Twórcy

autor

Stańczyk-Dunaj M.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Jarczewski A.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

Bibliografia

• 1.Muney W.S. and Coetzee J.F., J. Phys. Chem, 66, 89 (1962).
• 2.Chantooni M.K. and Kolthoff I.M., J. Am. Chem. Soc., 90, 3005 (1968).
• 3.Kolthoff I.M., Anal. Chem., 46, 1992 (1974).
• 4.Coetzee J.F., Padmanabhan G.R. and Cunningham G.P., Talanta, 11, 93 (1964).
• 5.Jarczewski A. and Hubbard C.D., J. Mol. Struct., 649, 287 (2003).
• 6.Gałęzowski W., Grzeskowiak I. and Jarczewski A., Can J. Chem., 77, 1042 (1999).
• 7.Gałęzowski W., Stanczyk M., Grzeskowiak I. and Jarczewski A.,Chem. Soc., Perkin Trans. 2, 2647 (1996).
• 8.Schroeder G., Łęska B., Jarczewski A., Nowak-Wydra B. and Brzezinski B., J. Mol. Struct., 344, 77 (1995).
• 9.Gałęzowski W., Jarczewski A., Stańczyk-Dunaj M., Brzeziński B., Bartl F. and Zundel C.,J. Chem. Soc. Faraday Trans., 93, 2515 (1997).
• 10.Coetzee J.F. and Padmanabhan G.R., J. Am. Chem. Soc., 87, 5005 (1965).
• 11.Approximated value.
• 12.Davis M.M. and Hetzer H.B., J. Res. Natl. Bur. Std., 48, 381 (1952).
• 13.Angyal S.J. and Warburton W.K., in Ross Stewart, The Proton: Applications to Organic Chemistry, Academic Press, INC, 1985, vol. 46, p. 89.
• 14.Leffek K.T., Pruszynski P. and Thanapaalasighan K., Can. J. Chem., 67, 590 (1989).
• 15.Schwesinger R., Chimia, 39, 269 (1985).
• 16.Perrin D.D., The Dissociation Constants for Organic Bases in Aqueous Solution, Butterworths, Londoi 1965.
• 17.Alder R.W., Bowman P.S., Steel W.R.S. and Winterman D.R., Chem. Commun., 723 (1968).
• 18.Kurasov L.A., Pozharskii A.F. and Kuzmenko V.V., Zh. Org Khim., 19, 859 (1983).
• 19.Schwesinger R., Willaredt J., Schlemper H., Keller M., Schmitt D. and Fritz H., Chem. Ber., 127, 243; (1994).
• 20.Belamy L.J., The Infrared Spectra of Complex Molecules, Chapman & Hall, London, 1975.
• 21.Kolthoff l.M. and Reddy T.B., Inorg. Chem., 1, 189 (1962).
• 22.Coetzee J.F. and Padmanabhan G.R., J. Phys. Chem., 66, 1708 (1962).
• 23.Kolthoff l.M. and Chantooni M.K., J. Am. Chem. Soc., 87, 4428 (1965).
• 24.Riddick J.A. and Bunger W.A., Organic Solvents -Physical Properties and Method of Purification, Nev York 1955, vol. 11.
• 25.Bredereck H. and Bredereck K., Chem. Ber., 94, 2278 (1961).