4-Nitrophenyl dodecanoate

Murakami et al. reported that a cyclophane 27 having two imidazole groups is activated by Cu2+ ions in the hydrolysis of p-nitrophenyl dodecanoate 25,26), although the activation seemed to be small. 

Kinetic investigations of the effects of urea and similar denaturing agents on rates and thermodynamic parameters of micelle catalyzed reactions have been suggested to be more sensitive probes for the nature and extent of hydrophobic interactions than CMC determinations. Thus, Monger and Portnoy (1968) have taken advantage of the base catalyzed hydrolysis of micellar -nitrophenyl dodecanoate. The rate constant for the hydrolysis of -nitrophenyl dodecanoate decreases rapidly with increasing initial concentration of the ester (10 to 10 m), and the second-order rate constant for the base-catalyzed hydrolysis of this ester... 

Shinkai S, Shirahama Y, Tsubaki T, Manabe O. Calixarene-catalyzed basic hydrolysis of p-nitrophenyl dodecanoate a possible change in the mechanism front deshielding to host-guest . J Am Chem Soc 1989 lll(14) 5477-8. 

CH3 phenylbutyrate (K = 1 mM) even though the medium contains 11% methanol and 2% acetonitrile. "Burst" kinetics is seen with all p-nitrophenyl esters, the size of the burst Indicating that only one hydroxamlc-acld group Is active. The acceleration over the reaction rate with N,N-diisobutylglycine N-methylhydroxamic acid, produced by 6, rises from 1.7x (p-nitrophenyl acetate) to 7600x (p-nitrophenyl dodecanoate)... 

Dissociation constants were determined from their inhibition of the reaction between HSA and p-nitrophenyl acetate as determined in pH 7.4, 0.03M triethanolamine / HCl at 25° C. Nonpolar surface areas were calculated according to Hermann (48/ The carboxylate ions are as follows (1) butyrate (2) valerate (3) hexanoate (4) heptanoate (5) octanoate (6) nonanoate (7) decanoate (8) undecanoate (9) dodecanoate (10) cyclohexanecarboxylate (11) 1-methyl-1-cyclohexanecarboxylate (12) cyclohexylacetate (13) 2-n-propylvalerate and... 

The effect of micellar solutions of sodium dodecanoate (laurate) and n-dodecyltrimethylammonium bromide on the rate of alkaline hydrolysis of p-nitrophenyl acetate, mono-p-nitrophenyl dodecanedioate, and p-nitrophenyl octanoate has been investigated by Menger and Portnoy... 

Fig. 6. Plots of for the hydrolysis of p-nitrophenyl acetate (A), mono-p-nltrophenyl dodecanedioate (B), and p-nitrophenyl ootanoate (C) at pH 9-59, I = 0-1 and 50° vs. sodium dodecanoate (laurate) concentration (on the left) and at pH 10-49, I = 0-2 and 50° vs. n-dodecyltrimethylammonium bromide (LTAB) concentration (on the right). Values of k,/, for the reaction of A -with sodium laurate have been divided by 2-0 to bring the curve on scale (Menger and Portnoy, 1967).

Effect of Additives on the Base Catalyzed Hydrolysis of Micellar jj-Nitrophenjd Dodecanoate and p-Nitrophenyl Acetate at 25° ... 

Rates of hydrolysis of p-nitrophenyl esters of alkanecarboxylic acids in the pH range 12-92 increased with chain length up to 27 times faster for the dodecanoic ester with soluble polymeric catalyst (56) than with 4-(l-pyrrolidinyl)pyridine as catalyst.Enhanced activity is attributed to the lower pX (7.8) of the conjugate acid of the polymer than of the soluble analogue pK 10.5), and to attraction of the lipophilic substrate to the polymer in an aqueous solution. Catalyst (57) bound to poly(ethyleneimine) was 2000 times more active than its monomeric analogue for hydrolysis of p-nitrophenyl caproate at pH 7.3. ... 

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