Protonation of polyacid organic bases. III. Hammett acidity function H+ for aqueous sulfuric acid

1968 ◽  
Vol 33 (6) ◽  
pp. 1687-1692 ◽  
Author(s):  
P. Vetešník ◽  
J. Bielavský ◽  
M. Večeřa
Keyword(s):  
Sulfuric Acid ◽  
Acidity Function ◽  
Organic Bases ◽  
Aqueous Sulfuric Acid ◽  
Hammett Acidity Function

A Critical Test of the Hammett Acidity Function

1972 ◽  
Vol 50 (4) ◽  
pp. 581-583 ◽  
Author(s):  
Keith Yates ◽  
Stanley A. Shapiro
Keyword(s):  
Sulfuric Acid ◽  
Aromatic Amines ◽  
Acidity Function ◽  
Experimental Uncertainty ◽  
Critical Test ◽  
Hammett Acidity Function ◽  
Primary Aromatic Amines

The applicability of the H0 acidity function to primary aromatic amines in general has been tested by using a set of five aniline indicators bearing no nitro-substituents. Up to 45% sulfuric acid the scale generated by these bases is the same (within experimental uncertainty) as that based entirely on nitro-anilines.

Applicability of the HT acidity function to the protonation of thioamides, thioureas, and thionesters

1977 ◽  
Vol 55 (12) ◽  
pp. 2331-2335 ◽  
Author(s):  
John T. Edward ◽  
Gary D. Derdall ◽  
Sin Cheong Wong
Keyword(s):  
Free Energy ◽  
Sulfuric Acid ◽  
Protonation Constants ◽  
Acidity Function ◽  
Linear Free Energy Relationships ◽  
Acceptable Accuracy ◽  
Aqueous Sulfuric Acid ◽  
Linear Free Energy ◽  
Energy Relationships

The protonation of eleven thioamides, five thioureas, and four thionbenzoates in aqueous sulfuric acid has been found to follow the HT acidity function with acceptable accuracy. Protonation constants pKTH+ obtained by use of HT agreed fairly well with pKTH+ values obtained by the Bunnett–Olsen method, but less well with those obtained by the Marziano–Cimino–Passerini procedure. Linear free-energy relationships of pKTH+ values are discussed.

Equilibrium protonation of the 1,3,5-trinitrobenzene–phenoxide σ-complex

1976 ◽  
Vol 54 (15) ◽  
pp. 2436-2444 ◽  
Author(s):  
Erwin Buncel ◽  
Walter Eggimann
Keyword(s):  
Sulfuric Acid ◽  
Hydrochloric Acid ◽  
Hydrogen Chloride ◽  
Picric Acid ◽  
Aqueous Media ◽  
Acidity Function ◽  
Acidic Properties ◽  
Aqueous Sulfuric Acid ◽  
Conjugate Acid ◽  
Nitronic Acid

The protonation behavior of the trinitrobenzene–phenoxide σ-complex has been determined in aqueous sulfuric acid, aqueous hydrochloric acid, and ethanolic hydrogen chloride. The conjugate acid of the σ-complex, a nitronic acid, exhibits acidic properties similar to those of picric acid and the cyanocarbon acids. The acidity (pKa) of the nitronic acid has been evaluated with the aid of various acidity function techniques and using the Bunnett–Olsen method. The nitronic acid is ca. 1 pK unit stronger than picric acid. However, both the nitronic acid and picric acid are considerably weaker acids in ethanolic than in aqueous media (ΔpK ca. 4 units). The results provide a preliminary H− acidity function scale for aqueous and ethanolic hydrogen chloride.

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