Carbon protonation of some phenylynamines in concentrated aqueous perchloric acid solution. Lowering of the upper limit for the pKa of phenylynammonium ions

Canadian Journal of Chemistry

Volumn 74, Issue 7, 1996, Pages 1373-1376

  Kresge, A J ^a   Paine, S W ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Acetylenic amines; Concentrated acids; Cox Yates method; Marcus rate theory; X0 excess acidity scale

Indexed keywords

AMINES; CARBON; IONS; ORGANIC ACIDS; PH; PH EFFECTS; SOLUTIONS;

ACETYLENIC AMINES; BASE WEAKENING EFFECT; CARBON PROTONATION; CONCENTRATED ACIDS; MARCUS RATE THEORY; NITROGEN PROTONATION; PHENYLYNAMMONIUM IONS;

CHEMICAL REACTIONS;

EID: 0030197023     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-155     Document Type: Article

References (16)

1. Y. Chiang, A.J. Kresge, R. Hochstrasser, and J. Wirz. J. Am. Chem. Soc. 111, 2355 (1989); J. Andraos, Y. Chiang, A.S. Grant, H.-X. Guo, and A.J. Kresge. J. Am. Chem. Soc. 116, 7411 (1994); Y. Chiang, A.J. Kresge, and V.V. Popik. J. Am. Chem. Soc. 117, 9165 (1995).
2. Y. Chiang, A.J. Kresge, R. Hochstrasser, and J. Wirz. J. Am. Chem. Soc. 111, 2355 (1989); J. Andraos, Y. Chiang, A.S. Grant, H.-X. Guo, and A.J. Kresge. J. Am. Chem. Soc. 116, 7411 (1994); Y. Chiang, A.J. Kresge, and V.V. Popik. J. Am. Chem. Soc. 117, 9165 (1995).
3. Y. Chiang, A.J. Kresge, R. Hochstrasser, and J. Wirz. J. Am. Chem. Soc. 111, 2355 (1989); J. Andraos, Y. Chiang, A.S. Grant, H.-X. Guo, and A.J. Kresge. J. Am. Chem. Soc. 116, 7411 (1994); Y. Chiang, A.J. Kresge, and V.V. Popik. J. Am. Chem. Soc. 117, 9165 (1995).
4. (a) Y. Chiang, A.S. Grant, A.J. Kresge, P. Pruszynski, N.P. Schepp, and J. Wirz. Angew. Chem. Int. Ed. Engl. 30, 1356 (1991);
5. (b) Y. Chiang, A.S. Grant, A.J. Kresge, and S.W. Paine. J. Am. Chem. Soc. 118, 4366 (1996).
6. B.J. Smith, L. Radom, and A.J. Kresge. J. Am. Chem. Soc. 111, 8297 (1989); B.J. Smith and L. Radom. J. Am. Chem. Soc. 114, 36 (1992).
7. B.J. Smith, L. Radom, and A.J. Kresge. J. Am. Chem. Soc. 111, 8297 (1989); B.J. Smith and L. Radom. J. Am. Chem. Soc. 114, 36 (1992).
8. Y. Chiang, M. Hojatti, J.R. Keeffe, A.J. Kresge, N.P. Schepp, and J. Wirz. J. Am. Chem. Soc. 109, 4000 (1987).
9. J. Andraos, Y. Chiang, G.-C. Huang, A.J. Kresge, and J.C. Scaiano. J. Am. Chem. Soc. 115, 10605 (1993).
10. R.A. Cox and K. Yates. Can. J. Chem. 59, 2116 (1981).
11. A.J. Kresge, H.J. Chen, G.L. Capen, and M.F. Powell. Can. J. Chem. 61, 249 (1983).
12. A. Bagno, G. Scorrano, and R.A. More O'Ferrall. Rev. Chem. Intermed. 7, 313 (1987).
13. A.J. Kresge. In Proton transfer reactions. Edited by E.F. Caldin and V. Gold. Chapman and Hall, London. 1975. pp. 179-199.
14. R.A. Marcus. J. Phys. Chem. 72, 891 (1968); A.J. Kresge. Chem. Soc. Rev. 2, 475 (1993).
15. R.A. Marcus. J. Phys. Chem. 72, 891 (1968); A.J. Kresge. Chem. Soc. Rev. 2, 475 (1993).
16. H.K. Hall. J. Am. Chem. Soc. 79, 5441 (1957).