593. Acid dissociation constants of the ammonium group in 2-aminoethanol, 2-aminoethyl phosphate, and 2-aminoethyl sulphate

1962 ◽  
pp. 3068 ◽  
Author(s):  
S. P. Datta ◽  
A. K. Grzybowski
Keyword(s):  
Dissociation Constants ◽  
Acid Dissociation ◽  
Acid Dissociation Constants ◽  
Ammonium Group

Nuclear magnetic resonance studies of the acid–base chemistry of amino acids and peptides. III. Determination of the microscopic and macroscopic acid dissociation constants of α,ω-diaminocarboxylic acids

1976 ◽  
Vol 54 (21) ◽  
pp. 3392-3400 ◽  
Author(s):  
Thomas L. Sayer ◽  
Dallas L. Rabenstein
Keyword(s):  
Chemical Shift ◽  
Dissociation Constants ◽  
Nonlinear Least Squares ◽  
Acid Dissociation ◽  
Acid Base ◽  
Acid Dissociation Constants ◽  
Ammonium Group ◽  
Titration Curves ◽  
Chemical Shift Titration ◽  
The Difference

The acid–base chemistry of 2,3-diaminopropionic acid (dap), 2,4-diaminobutyric acid (dab), ornithine (orn), and lysine (lys) has been studied by 13C and proton nmr spectroscopy. Macroscopic acid dissociation constants for titration of the two ammonium groups of each molecule have been calculated from the 13C chemical shift titration curves for the alkyl carbon atoms by nonlinear least squares curve fitting methods. Microscopic acid dissociation constants for the simultaneous titration of the two ammonium groups of protonated orn and lys have been obtained from their proton chemical shift titration curves and from the 13C titration curves for orn and dap. The results indicate that the α-ammonium group of each of these α,ω-diaminocarboxylic acids is more acidic than its ω-ammonium group, but that the difference decreases as the number of carbons separating the ammonium groups decreases so that the acidities of the two ammonium groups of dap are almost identical. Results of pmr studies of the acid–base chemistry of glycyl-L-lysine and L-lysylglycine also are reported.

Substituent effects on polarographic reduction of some photographic color intermediates

1976 ◽  
Vol 54 (8) ◽  
pp. 1205-1210 ◽  
Author(s):  
Ahmad S. Shawali ◽  
Bahgat E. El-Anadouli
Keyword(s):  
Dissociation Constants ◽  
Substituent Effects ◽  
Protonated Form ◽  
Acid Dissociation ◽  
Polarographic Reduction ◽  
Substituent Constant ◽  
Acid Dissociation Constants ◽  
Controlled Potential Electrolysis ◽  
Half Wave ◽  
Controlled Potential

Polarographic reduction of two series of benzoylacetanilides has been investigated in 40% (by volume) ethanolic Britton–Robinson buffers. One series (A) contains substituents on the anilide moiety, and the second (B) has substituents on both the anilide and benzoyl moieties. Polarographic controlled-potential electrolysis data indicate that the electroactive species in both series is the protonated form (ArCOCH2CONHAr′)H+. The reduction half-wave potentials of anilides of series A were found to be independent of the nature of the substituent, whereas those of series B show a good linear relationship when plotted vs. the σ substituent constant of the substituent on the benzoyl moiety (ρ = 0.284, r = 0.995). Values of the acid dissociation constants of the keto (K1) and enol (K2) tautomers of the anilides of series A were calculated; unlike their E1/2 values, the pK1 data show a linear correlation with the Hammett substituent constant, σ. The pK2 values show, however, little variation with σ.

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