288-88-0Relevant articles and documents
Kinetics of hydrolysis in aqueous solution of 1-benzoyl-1,2,4-triazole; the role of pairwise and triplet Gibbs energy interaction parameters in describing the effects of added salts and added alcohols
Noordman, Wouter H.,Blokzijl, Wilfried,Engberts, Jan B. F. N.,Blandamer, Michael J.
, p. 1411 - 1414 (1995)
Kinetic data are reported for the spontaneous hydrolysis of 1-benzoyl-1,2,4-triazole in aqueous solutions at ambient pressure and 298.2 K, in aqueous solutions containing added ethanol, propanol and sodium chloride.Kinetic data are also reported for the same reaction in aqueous mixtures of sodium chloride and ethanol.When either ethanol or propanol are added the rate constant k decreases, plotes of ln(k) vs. molality of alcohol being linear.The patterns are accounted for using pairwise Gibbs energy interaction parameters.The rate constant k decrease more dramatically when sodium chloride is added.This pattern is accounted for using pairwise and triplet interaction parameters.The dependence of rate constant on molality of added ethanol in solutions containing fixed molalities of sodium chloride deviaties from that predicted using the pairwise interaction parameters indicating a non-additivity of salt and alcohol effects on the rate constant.The deviations increase wirh increase in molalities of both added salt and added solvent in a direction consistent with a disruption of the substrate-alcohol hydrophobic interactions by added salt.
Kinetic Medium Effects of Amphiphilic Cosolutes below Their Critical Micelle Concentration: The Effect of Sodium n-Alkyl Sulfates on the Neutral Hydrolysis of 1-Benzoyl-1,2,4-triazole
Noordman, Wouter H.,Blokzijl, Wilfried,Engberts, Jan B. F. N.,Blandamer, Michael J.
, p. 7111 - 7114 (1993)
Kinetic medium effects are presented for sodium n-alkyl sulfates (R = methyl to n-octyl) on the neutral hydrolysis of 1-benzoyl-1,2,4-triazole at 298.15 K in highly aqueous solutions below the critical micellar concentration.The observed rate-decreasing effects are quantitatively analyzed in terms of pairwise solute-solute interactions.It is shown that the effect of the alkyl chains cannot be accounted for on the basis of additivity of pairwise group interactions involving individual methylene moieties.Apparently, the sulfate group shields methylene moieties in close proximity for intermolecular interactions.Methylene groups, further away from the ionic functionality, are shielded less effectively.At the critical micellar concentration of the longer-chain sodium n-alkyl sulfates, the observed medium effects change dramatically as expected on the basis of the onset of micellization.No clear indication for premicellar aggregation was found.The medium effect of the sulfate moiety is estimated by extrapolation of kinetic medium effects to zero methylene groups and appears to be rate-retarding as well.
Kinetics of hydrolysis of 1-benzoyl-1,2,4-triazole in aqueous solution as a function of temperature near the temperature of maximum density, and the isochoric controversy
Blandamer, Michael J.,Buurma, Niklaas J.,Engberts, Jan B.F.N.,Reis, Joao C.R.
, p. 720 - 723 (2003)
At temperatures above and below the temperature of maximum density, TMD, for water at ambient pressure, pairs of temperatures exist at which the molar volumes of water are equal. First-order rate constants for the pH-independent hydrolysis of 1-benzoyl-1,2,4-triazole in aqueous solution at pairs of such isochoric temperatures show no unique features. Taken together with previously published kinetic data for the hydrolysis of a range of simple organic solutes in both water and D2O near their respective TMDs, we conclude that special significance in the context of rates of chemical reactions in aqueous solutions should not be attached to the isochoric condition.
Water-Catalyzed Amide Hydrolysis in Dilute Aqueous Carbohydrate Solutions
Nusselder, Jan Jaap H.,Engberts, Jan B. F. N.
, p. 3159 - 3162 (1987)
Rates and thermodynamics activation parameters were determined for the water-catalyzed hydrolysis of the activated amide bond in three 1-acyl-1,2,4-triazoles of different hydrophobicity by using dilute aqueous solutions of simple carbohydrates as the reaction medium.The solutions show thermodynamically almost ideal behavior.It appears that the kinetic medium effects, and, in particular, the changes in ΔS. are largely determined by carbohydrate-induced alterations in the three-dimensional hydrogen-bond network of water.The specific, hydration model for carbohydrates, developed by Franks and his associates, appears to provide a key to the understanding of the carbohydrate medium effects on the hydrolytic model reaction
Water-Catalyzed Hydrolysis of 1-Acyl-1,2,4-triazoles in the Presence of Surfactant-Polymer Mixed Micelles. Substrate Dependence of the Effect of Polymer on the Micellar Inhibition
Fadnavis, Nitin W.,Berg, Henk-Jan van den,Engberts, Jan B. F. N.
, p. 48 - 52 (1985)
The water-catalyzed hydrolysis of 1-benzoyl-1,2,4-triazole (1) is inhibited by SDS micelles.Addition of poly(vinylalcohol)-poly(vinyl acetate) copolymers (17percent and 26percent acetate, respectively) leads to a decreased inhibition.As supported by conductivity measurements, the rate effects are attributed to the formation of SDS-copolymer mixed micelles.Ultrafiltration experiments indicate increased binding of the substrate to the mixed micelles.Therefore the copolymer-induced rate accelerations can be best reconciled with an increase in the micropolarity at the substrate binding sites in the mixed micelles relative to unperturbed SDS micelles.With the aid of a computer, all kinetic data can be fitted into a kinetic scheme assuming hydrolysis of 1 in bulk water and in SDS and SDS-copolymer micellar pseudophases.Hydrolysis in SDS-poly(N-vinylpyrrolidone) (PVP) mixed micelles at low SDS concentrations (3-10 mM) was studied with the more hydrophobic substrate 3-phenyl-1-benzoyl-1,2,4-triazole (3).Now the SDS-induced inhibition is further increased by the polymer.Kinetic analysis shows that 3 is less strongly bound to mixed SDS-PVP micelles than to SDS micelles but that the rate constants in both micellar pseudophases are rather similar.It is argued that the different behavior of 1 and 3 in the mixed micelles primarily reflects the large propensity of 3 for stabilization by hydrophobic interactions.
Micellar Inhibition of the Neutral Hydrolysis of 3-Substituted 1-Benzoyl-1,2,4-triazoles. Microenvironmental Effects at the Surface of Sodium Dodecylsulfate and Cetyltrimethylammonium Bromide Micelles
Fadnavis, Nitin,Engberts, Jan B. F. N.
, p. 152 - 154 (1982)
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Dearomatization of oxa- or selenadiazolopyridines with neutral nucleophiles as an efficient approach to pharmacologically relevant nitrogen compounds
Starosotnikov, Alexey M.,Shkaev, Dmitry V.,Bastrakov, Maxim A.,Fedyanin, Ivan V.,Shevelev, Svyatoslav A.,Dalinger, Igor L.
, p. 638 - 640 (2018/12/13)
Highly electrophilic 6-nitro-4-azabenzofuroxan and 6-nitro-4-azabenzo[1,2,5]selenadiazole add π-excessive (het)arenes and other neutral nucleophiles at 7-position to give C–C and N–C-bonded adducts, 1,4-dihydropyridines fused with furoxan or selenadiazole ring.
Synthesizing process of 1H-1,2,4-triazole
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Paragraph 0074; 0075; 0076;, (2016/11/28)
The invention discloses a synthesizing process of 1H-1,2,4-triazole, comprising the following synthesizing steps: (1) adding formic ether, hydrazine hydrate and ammonium salt in sequence into a high-pressure reaction kettle, pressurizing the reaction kettle and gradually heating up to a reaction temperature under a sealed stirring state, gradually lowering down the reaction temperature after the reaction is complete and using the after heat to evaporate the byproduct methyl alcohol, thereby obtaining a white emulsion matter; (2) transferring the white emulsion matter into the reaction kettle, adding ethyl alcohol, heating and refluxing to obtain a mixture solution, hot filtering the mixture solution by a filter cartridge into a crystallization kettle, cooling the filtrate inside the crystallization kettle to room temperature, separating out white crystals, drying by a hot air drying oven after centrifugal separation, thereby obtaining the 1H-1,2,4-triazole. The synthesizing process of the 1H-1,2,4-triazole allows the hydrazine hydrate to react with the formamide which is obtained by direct ammonolysis of the ammonia obtained from the decomposition of the formic ether and the ammonium salt under the high temperature conditions, thereby effectively increasing the entire chemical reaction speed, reducing the reaction temperature and increasing the product output, with simple overall synthesizing process, lower energy consumption and few three-waste discharge.
A new class of bioactivable self-immolative N,O-ligands
Ku?nik, Nikodem,Chrobaczyński, Arkadiusz,Mika, Ma?gorzata,Miler, Patrycja,Komor, Roman,Kubicki, MacIej
supporting information; experimental part, p. 184 - 192 (2012/07/28)
A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by β-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives.
