98-47-5Relevant articles and documents
Effect of solvent on the kinetics of arylsulfonylation of N-alkylated anilines in a water-propan-2-ol system
Kustova,Sterlikova
, p. 973 - 975 (2006)
The effect of the composition of a water-propan-2-ol solvent on the kinetics of arylsulfonylation of N-ethyl-, N-isopropyl-, and N-butylanilines with 3-nitrobenzenesulfonyl chloride at 298 K was studied. The reaction rate constant increases monotonically with an increase in the water fraction in the solvent from 5 to 30 wt.%. The apparent activation parameters of the reaction of N-butylaniline with 3-nitrobenzenesulfonyl chloride were calculated. No considerable changes in the activation parameters of the reaction were observed on going from pure propan-2-ol to a 10% aqueous solution, which indicates that the mechanism remains unchanged upon solvent change. Propan-2-ol with a water content of 5-30 wt.% can be used in the synthesis of arylsulfonylation products of the amines under study in 98-99% yield.
Reactivity of Benzamide toward Sulfonylation
Kochetova, L. B.,Kruglyakova, A. A.,Kustova, T. P.
, p. 1098 - 1102 (2021/09/08)
Abstract: The ranges of variation of the rate constant (0.031– 0.153L·mol–1·s–1), energyof activation (21– 55 kJ/mol), and entropy of activation (88–191J·mol–1·K–1) for thereaction of benzamide with 3-nitrobenzenesulfonyl chloride in aqueous1,4-dioxane with a concentration of water of 15–40 wt % have been determined bystudying the reaction kinetics in the temperature range 298–313 K. The potentialenergy surface for the gas-phase reaction of benzamide with3-nitrobenzenesulfonyl chloride has been simulated at the DFT B3LYP/6-311G(d,p) level of theory; the results of quantum chemical simulationsuggest bimolecular nucleophilic substitution mechanism of this reaction.
Reactivity of 2-Sulfobenzoic Acid Imide and Benzenesulfonamide in Arenesulfonylation
Kustova,Agafonov,Kruglyakova,Kochetova
, p. 792 - 795 (2019/08/02)
Experimental study of the kinetics of the reactions of 2-sulfobenzoic acid imide (saccharin) and benzenesulfonamide with 3-nitrobenzenesulfonyl chloride in a 1,4-dioxane-water mixture (80:20 by weight) in the temperature range 298–318 K has shown that both compounds are low reactive (k298 = 1.66 × 10?4 and 3.37 × 10?3 L mol?1 s?1, respectively). The activation barriers to these reactions exceed 50 kJ/mol. Aqueous dioxane can be recommended as a solvent for the preparation of N-(benzenesulfonyl)-3-nitrobenzenesulfonamide in up to 87% yield.
Regioselective Sulfonation of Aromatic Compounds over 1,3-Disulfonic Acid Imidazolium Chloride under Aqueous Media
Moosavi-Zare, Ahmad Reza,Zolfigol, Mohammad Ali,Noroozizadeh, Ehsan
, p. 1682 - 1684 (2016/07/06)
1,3-Disulfonic acid imidazolium chloride ([Dsim]Cl), as a Bronsted acidic ionic liquid, is introduced for the sulfonation of aromatic compounds by in situ generation of sulfuric acid at 50 °C under mild conditions and in aqueous medium.
