scholarly journals Schiff base equilibria. VII. Formation and distribution of N-(β-Hydroxyethyl)salicylideneimine

1969 ◽  
Vol 22 (5) ◽  
pp. 917 ◽  
Author(s):  
RW Green ◽  
RJ Sleet

The formation constant and pK of the Schiff base N-(8- hydroxyethyl)salicylideneimine in aqueous solution at 25� have been determined spectrophotometrically to be 5.01 x 103 and 11.4 respectively. These equilibrium constants have been used to account for the distribution of the imine between water and chloroform.

1968 ◽  
Vol 21 (10) ◽  
pp. 2427 ◽  
Author(s):  
RW Green ◽  
MJ Rogerson

Equilibrium constants at 25� have been measured for the formation of Schiff bases of pyridine-2-aldehyde with n-butylamine (1.45 x 108) and t-butylamine (93). The Schiff base of salicylaldehyde with t-butylamine has a formation constant 9.1 x 108 and pK 13.0.


1973 ◽  
Vol 26 (8) ◽  
pp. 1653 ◽  
Author(s):  
RW Green ◽  
PW Alexander ◽  
RJ Sleet

Equilibria between salicylaldehyde and three aliphatic diamines, ethylenediamine, trimethylenediamine, and 1,3-diaminopropan-2-ol, have been measured in aqueous solution containing a large excess of diamine to suppress hydrolysis. Equilibrium constants are reported for the formation and acid-base reactions of the mono-salicylideneimines formed from the three diamines. It is demonstrated that there are no conditions under which detectable concentrations of bis- salicylideneimines exist in aqueous solution.


1965 ◽  
Vol 18 (5) ◽  
pp. 651 ◽  
Author(s):  
RW Green ◽  
PW Alexander

The Schiff base, N-n-butylsalicylideneimine, extracts more than 99.8% beryllium into toluene from dilute aqueous solution. The distribution of beryllium has been studied in the pH range 5-13 and is discussed in terms of the several complex equilibria in aqueous solution. The stability constants of the complexes formed between beryllium and the Schiff base are log β1 11.1 and log β2 20.4, and the distribution coefficient of the bis complex is 550. Over most of the pH range, hydrolysis of the Be2+ ion competes with complex formation and provides a means of measuring the hydrolysis constants. They are for the reactions: Be(H2O)42+ ↔ 2H+ + Be(H2O)2(OH)2, log*β2 - 13.65; Be(H2O)42+ ↔ 3H+ + Be(H2O)(OH)3-, log*β3 -24.11.


1988 ◽  
Vol 66 (12) ◽  
pp. 3184-3189 ◽  
Author(s):  
Mohamed M. Shoukry ◽  
Bruce V. Cheesman ◽  
Dallas L. Rabenstein

The complexation of Hg(II) by glutathione has been studied by polarimetry under conditions of excess ligand with the objective of characterizing formation of the 3:1 complex, Hg(glutathione)3. The optical rotatory power of solutions containing glutathione only and of solutions containing glutathione and Hg(II) at ratios of 2:1, 2.5:1, 3:1, and 4:1 was measured as a function of pH. Acid dissociation constants for the ammonium and thiol groups of glutathione and for the two ammonium groups of Hg(glutathione)2 and the formation constant of the 3:1 complex (Hg(glutathione)2 + glutathione [Formula: see text] Hg(glutathione)3) were determined from the pH dependence of the optical rotatory power. The value obtained for the formation constant, Kf = 1.5 × 103, indicates that binding of the third ligand to form Hg(glutathione)3 is much weaker than binding of the first two glutathione ligands. However, calculations indicate that binding is sufficiently strong that a significant fraction of Hg(II) is present as Hg(glutathione)3 under physiological conditions. Equilibrium constants were also determined by polarimetry and by 13C nuclear magnetic resonance for the displacement of one thiolate ligand by another (RSHgSR + R′SH [Formula: see text] RSHgSR′ + RSH; RSHgSR′ + R′SH [Formula: see text] R′SHgSR′ + RSH). The results indicate that, at pH 5.5 and at physiological pH, the relative stability increases in the order Hg(glutathione)2 < Hg(penicillamine)2 < Hg(mercaptoethylamine) 2. However, when competitive protonation of free ligand is accounted for, it is shown that the intrinsic stability of the complexes increases in the order Hg(penicillamine)2 < Hg(mercaptoethylamine)2 < Hg(glutathione)2, which parallels the order of the Brønsted basicity of the thiolate ligands.


1995 ◽  
Vol 50 (4) ◽  
pp. 545-550 ◽  
Author(s):  
Masaaki Tabata ◽  
Masahiro Ide ◽  
Kentaro Kaneko

Thermochromism was observed for an aqueous solution containing zinc(II) and mercury( II) cations and N-p-nitrobenzyl-5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin anion (NO2Bz(Htpps)4-) in the temperature range 10 to 70 °C. The equilibrium constants and the thermodynamic parameters of Zn(NO2Bztpps)3- and Hg(NO2Bztpps)3- have been determined spectrophotometrically to elucidate the thermochromism at 10, 15, 20, 25 and 30 °C in 0.1 mol dm-3 NaNO3. The protonation and metalation constants of NO2Bz(Htpps)4- are defined as K2 = [H2P][H+]-1[HP]-1, K3 = [H3P][H+]-1[H2P]-1 and KMP = [M P][H+][M2+]-1[HP]-1, where HP and MP denote the free base form of the prophyrin and the metalloporphyrins of zinc(II) and mercury(II), respectively. Charges of the prophyrin and metalloporphyrins are omitted for simplicity. The following values were found: logK2 = 7.75 ±0.02 (25 °C), ΔH°/kJmol-1 = -21.2±0.5 and ΔS°/Jmol-1K-1 = 77±1, logK3 = 2.55±0.02 (25 °C), ΔH°/kJmol-1 = -25±0.8 and ΔS°/Jmol-1K-1 = -35±3 and log KZnP = 0.63±0.03 (25 °C), ΔH°/kJmol-1 = 31.0±0.8 and ΔS°/Jmol-1K-1 = 116±3, logKHgP = 6.22±0.03 (25 °C), ΔH°/kJmol-1 = 4.5±0.7 and ΔS°/Jmol-1K-1 = 134±2. The distribution curve calculated from the thermodynamic parameters sufficiently agrees with the observed metal exchange reaction between the metalloporphyrins.


1965 ◽  
Vol 18 (3) ◽  
pp. 329 ◽  
Author(s):  
RW Green ◽  
PW Alexander

The equilibrium constant governing the formation of a Schiff base from salicylaldehyde and n-butylamine in aqueous solution has been evaluated by spectrophotometry as 5.62 x 104. The pK of the phenolic group of the Schiff base is 12.0. These constants have been used to account for the distribution of salicylaldehyde between water and toluene in the presence of butylamine. The neutral form of the Schiff base has a distribution coefficient of 1.9 x 103.


2018 ◽  
Vol 10 (20) ◽  
pp. 2317-2326 ◽  
Author(s):  
Amit Kumar Manna ◽  
Jahangir Mondal ◽  
Rukmani Chandra ◽  
Kalyani Rout ◽  
Goutam Kumar Patra

A fluorescent-colorimetric azo dye based bis-Schiff base chemosensor, L, has been developed. L can selectively detect S2− through a color change from yellow to orange in perfect aqueous solution by deprotonation mechanism.


2018 ◽  
Vol 24 (2) ◽  
pp. 93-97
Author(s):  
Shaoxin Li ◽  
Wei Kan ◽  
Bing Zhao ◽  
Ting Liu ◽  
Yue Fang ◽  
...  

AbstractThe pH fluorescent probe 7-hydroxy-4-methyl-8-(((2-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)imino)methyl)-2H-chromen-2-one (PICO) contains a donor–π–acceptor (D–π–A) conjugated system. The ‘off−on’ probe PICO has a pKa value of 8.01 and its fluorescence intensity is enhanced with increasing pH.


2020 ◽  
Vol 44 (45) ◽  
pp. 19642-19649
Author(s):  
Lingjie Hou ◽  
Tao Liu ◽  
Yaling Gong ◽  
Jin Li ◽  
Chenhua Deng ◽  
...  

A Schiff base fluorescent probe, namely naphthalic anhydride – (2-pyridine) hydrazone (NAH), has been synthesized and developed for the highly selective and sensitive monitoring of Fe3+ ions in an aqueous solution and living cells.


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