Protonation Equilibria of Tertiary Anilines in Sulfuric Acid: Water as a Reactant

1983 ◽  
Vol 136 (136) ◽  
pp. 65-67
Author(s):  
Michael W. Lovell ◽  
Brian S. Vogt ◽  
Stephen G. Schulman
2016 ◽  
Vol 121 (4) ◽  
pp. 1736-1751 ◽  
Author(s):  
Joonas Merikanto ◽  
Jonathan Duplissy ◽  
Anni Määttänen ◽  
Henning Henschel ◽  
Neil M. Donahue ◽  
...  

1998 ◽  
Vol 108 (16) ◽  
pp. 6829-6848 ◽  
Author(s):  
I. Kusaka ◽  
Z.-G. Wang ◽  
J. H. Seinfeld

2011 ◽  
Vol 7 ◽  
pp. 1732-1738 ◽  
Author(s):  
José A Moreira ◽  
Ana M Rosa da Costa ◽  
Luis García-Río ◽  
Márcia Pessêgo

The protonation equilibria of four substituted N-methylbenzenesulfonamides, X-MBS: X = 4-MeO (3a), 4-Me (3b), 4-Cl (3c) and 4-NO2 (3d), in aqueous sulfuric acid were studied at 25 °C by UV–vis spectroscopy. As expected, the values for the acidity constants are highly dependent on the electron-donor character of the substituent (the pK BH+ values are −3.5 ± 0.2, −4.2 ± 0.2, −5.2 ± 0.3 and −6.0 ± 0.3 for 3a, 3b, 3c and 3d, respectively). The solvation parameter m* is always higher than 0.5 and points to a decrease in the importance of solvation on the cation stabilization as the electron-donor character of the substituent increases. Hammett plots of the equilibrium constants showed a better correlation with the σ+ substituent parameter than with σ, which indicates that the initial protonation site is the oxygen atom of the sulfonyl group.


1974 ◽  
Vol 61 (2) ◽  
pp. 573-581 ◽  
Author(s):  
R. H. Heist ◽  
H. Reiss
Keyword(s):  

Sign in / Sign up

Export Citation Format

Share Document