45900-71-8

Upstream product

• 52008-62-5 n-butyl-4-bromobenzenesulfonate 
• 6213-85-0 Methyl 4-brosylate 
• 1213779-63-5 8-(4-bromobenzenesulfonyloxy)-5-N,N-dimethylaminosulfonylquinaldine 
• 98-58-8 4-bromobenzenesulfonyl chloride 

Relevant academic research and scientific papers

The Hammett equation applied to the nucleophilic displacement of ions and ion pairs on substituted benzenesulphonates

Nucleophilic substitution on meta- and para-substituted methyl benzenesulphonates was studied with two chloride salts with different structures: NBu4Cl or KCl-Kryptofix 2,2,2. Treating the results with the Acree equation shows that the reaction proceeds by two reaction paths, one involving the chloride ion and the other, slower one, involving the ion pairs. Treating the results with the Hammett equation gives consistent data, and shows that ρ is positive and nearly the same for the two reaction paths (ρ ≈ +2). The reactivity of methyl p-nitrobenzenesulphonate was compared with that of the corresponding ethyl derivative, and it is shown that the methyl derivative reacts faster than the ethyl derivative in both paths. The results are interpreted based on the assumption that in both paths a negative charge is developed on the leaving group in the transition state, and that the activated complex is linear. Copyright

Photochemical cleavage reactions of 8-quinolinyl sulfonates in aqueous solution

Photochemical cleavage reactions of 8-quinolinyl benzenesulfonate derivatives and related sulfonates in aqueous solutions are reported. The 8-quinolinyl benzenesulfonates undergo photolysis upon photoirradiation at 300-330 nm to give the corresponding 8-quinolinols and benzenesulfonic acids with the production of only negligible amounts of byproducts. The effects of substituent groups of the 8-quinolinyl moiety and the benzene ring on the photolysis reactions were examined. Based on steady-state mechanistic studies using a triplet sensitizer, a triplet quencher, and electron donors, it was suggested that the photolysis proceeds mainly via the homolytic cleavage of S-O bonds in the excited triplet state.

The Hammett equation and micellar effects on SN2 reactions of methyl benzenesulfonates - The role of micellar polarity

Substituent effects on the reaction of H2O, OH-, and Br- with p-substituted methyl benzenesulfonates in cationic micelles of cetyl trialkylammonium ion surfactants (n-C16H33NR3X, X = OH, Br, R = Me, Et, nPr, nBu) and in water were analyzed by using the Hammett equation. Values of p in the various media confirm that micellar interfacial regions are less polar than water and polarities decrease with increasing bulk of the surfactant head-group. Wiley-VCH Verlag GmbH, 2000.

NUCLEOPHILICITY OF HALIDE IONS IN THE MICELLAR PSEUDOPHASE

The reaction of Br(-) or Cl(-) with both n-butyl-4-nitrobenzenesulfonate and n-butyl-4-bromobenzenesulfonate 1a and 1b respectively is catalyzed by cationic micelles of cetyltrimethylammonium chloride or bromide (CTACl or CTABr respectively).The increase of rate constant with can be analyzed in terms of the concentration of substrate (1a-b) and halide ion in the micellar pseudophase, and the second-order rate constants in micellar and aqueous pseudophase are similar.

Micellar Effects upon Spontaneous and Carboxylate Ion Catalyzed Hydrolyses of Benzenesulfonyl Chlorides

Spontaneous hydrolyses of benzenesulfonyl chlorides are inhibited by micelles of cetyltrimethylammonium chloride (CTACl), sodium dodecyl sulfate (SDS), and N-hexadecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate (SB3-16).The rate constants for hydrolyses of fully bound substrates are similar in CTACl and SB3-16.The rate constants in CTACl (k+) and SDS (k-) depend on the electronic effects of the 4-substituents and k+/k- increases in the sequence MeO Me H Br NO2.These micellar charge effects are ascribed to changes in the extents of bond-making and -breaking in the transition state.Hydrolysis in micellized N-dodecyl-N,N-dimethylglycine (B1-12) is inhibited, but this effect is offset by nucleophilic participation by the carboxylate moiety.Electron-withdrawing substituents strongly favor nucleophilic participation and for the 4-bromo and 4-nitro derivatives second-order rate constants in zwittwerionic betaine micelles of B1-12 are similar to those for reaction with nonmicellized N,N,N-trimethylglycine in water.