3453-83-6Relevant academic research and scientific papers
Formation of a potassium coordination polymer based on a novel 2-sulfono-benzene-1,3,5-tricarboxylic acid: Synthesis, characterization, and application of the organocatalyst in CO2 cycloaddition reaction
Alavijeh, Masoumeh Karimi,Amini, Mostafa M.,Notash, Behrouz,Mohammadnezhad, Gholamhossein
, (2021)
In the present work, a new 3D potassium coordination polymer (1) was prepared by oxidation of sulfonated mesitylene. Its novel sulfono-tricarboxylic ligand, 2-sulfono-benzene-1,3,5-tricarboxylic acid (2), which acted as a structure-directing building block, was successfully synthesized by ion exchange of the potassium coordination polymer (1). The 3D coordination polymer and the sulfonate-carboxylate ligand were characterized by FT-IR and 1H and 13C NMR spectroscopies, and their molecular structures were determined by single-crystal X-ray diffraction. In addition, thermal stability and adsorption/desorption behavior of 1 was investigated by TGA-DTA and N2 adsorption/desorption techniques, respectively. The catalytic activities of the ligand, as a novel and simple organocatalyst, and the rarely explored potassium CPs were studied in the CO2 cycloaddition reaction. The results showed 2 is an efficient organocatalyst in the CO2 cycloaddition process. It is suggested that the synergetic effect among Br?nsted acid COOH, Lewis base I? and free water molecules facilitate this reaction.
Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions
Fatima, Touheeth,Duguta, Govardhan,Purugula, Venkanna,Yelike, Hemanth Sriram,Kamatala, Chinna Rajanna
, p. 1001 - 1006 (2020/07/27)
Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 in aqueous acetonitrile medium at room temperature within 1–4 h, while microwave assisted reactions took place within 1–4 min under solvent-free conditions. These observations indicate significant rate accelerations in microwave assisted reactions. which were explained due to the bulk activation of molecules induced by insitu generated high temperatures and pressures when microwaves are transmitted through reaction medium.
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.
Isotope Effects in the Solvolysis of Sterically Hindered Arenesulfonyl Chlorides
Iazykov, Mykyta,Canle L., Moisés,Santaballa, J. Arturo,Rublova, Ludmila
, p. 744 - 750 (2015/10/06)
Solvent isotope effects in the ethanolysis of sterically hindered arenesulfonyl chlorides ruled out a proton transfer in the rate-determining step and agreed with a SN2 mechanism involving at least a second solvent molecule in the transition state (TS). The lack of a secondary kinetic isotope effect in the o-alkyl groups allows us to disregard the possible contribution of σ-π hyperconjugation. The measured activation parameters are consistent with a SN2 mechanism involving the participation of solvent molecules in the TS, possibly forming a cyclic TS through a chain of solvent molecules.
Formation of the bisulfite anion (HSO3 -, m/z 81) upon collision-induced dissociation of anions derived from organic sulfonic acids
Jariwala, Freneil B.,Wood, Ryan E.,Nishshanka, Upul,Attygalle, Athula B.
experimental part, p. 529 - 538 (2012/08/28)
In the negative-ion collision-induced dissociation mass spectra of most organic sulfonates, the base peak is observed at m/z 80 for the sulfur trioxide radical anion (SO3 -·). In contrast, the product-ion spectra of a few sulfonates, such as cysteic acid, aminomethanesulfonate, and 2-phenylethanesulfonate, show the base peak at m/z 81 for the bisulfite anion (HSO3 - ). An investigation with an extensive variety of sulfonates revealed that the presence of a hydrogen atom at the β-position relative to the sulfur atom is a prerequisite for the formation of the bisulfite anion. The formation of HSO3 - is highly favored when the atom at the β-position is nitrogen, or the leaving neutral species is a highly conjugated molecule such as styrene or acrylic acid. Deuterium-exchange experiments with aminomethanesulfonate demonstrated that the hydrogen for HSO3 - formation is transferred from the β-position. The presence of a peak at m/z 80 in the spectrum of 2-sulfoacetic acid, in contrast to a peak at m/z 81 in that of 3-sulfopropanoic acid, corroborated the proposed hydrogen transfer mechanism. For diacidic compounds, such as 4-sulfobutanoic acid and cysteic acid, the m/z 81 ion can be formed by an alternative mechanism, in which the negative charge of the carboxylate moiety attacks the α-carbon relative to the sulfur atom. Experiments conducted with deuterium-exchanged and deuterium-labeled analogs of sulfocarboxylic acids demonstrated that the formation of the bisulfite anion resulted either from a hydrogen transfer from the β-carbon, or from a direct attack by the carboxylate moiety on the α-carbon. Copyright
A novel method for sulfonation of aromatic rings with silica sulfuric acid
Hajipour, Abdol R.,Mirjalili, Bi Bi F.,Zarei, Amin,Khazdooz, Leila,Ruoho
, p. 6607 - 6609 (2007/10/03)
Direct and chemoselective sulfonation of aromatic compounds with silica sulfuric acid in 1,2-dichloeoethane or under solvent-free conditions.
Nonmonotonic dependences of the activation parameters of hydrolysis of methyl-substituted benzenesulfonyl bromide on the composition of the dioxane-water binary solvent. The effect of hydrophobic interactions
Kislov,Ivanov,Gnedin
, p. 460 - 467 (2007/10/03)
Pseudo-first-order rate constants and activation parameters (ΔH≠ and ΔS≠) were determined for hydrolysis of 2-CH3- and 2,4,6-(CH3)3-substituted benzenesulfonyl bromide over wide ranges of temperature and compositions of the dioxane-water solvent. The dependences of the activation parameters on the mole fraction of dioxane (X2) are nonmonotonic, like those for the earlier studied hydrolysis of 4-toluenesulfonyl bromide. The X2 values (ranging from 0 to 0.13) corresponding to maximum Δ≠ and ΔS≠ are different for different methyl-substituted benzenesulfonyl bromides. Selective hydrophobic interactions water-sulfonyl bromide make the activation parameters reach maxima at such compositions of the binary solvent that allow each of the substrates to hydrolyze inside an individual quasi-clathrate solvation shell.
Reactivity of sterically hindered aromatic sulfonic acid derivatives: VII.* hydrolysis of arenesulfonyl chlorides in aqueous acetonitrile
Rubleva,Krut'ko,Mitchenko
, p. 1006 - 1009 (2007/10/03)
Hydrolysis of sterically hindered arenesulfonyl chlorides in aqueous acetonitrile is accelerated by both electron-acceptor and some electron-donor substituents in the benzene ring. A multifactor kinetic model of the process is proposed. 1998 MAHK Hayka/Interperiodica Publishing.
Sulphonyl Transfer Reactions: Solvolysis of Arenesulphonyl Chlorides in Aqueous Trifluoroethanol
Forbes, Rowena M.,Maskill, H.
, p. 854 - 856 (2007/10/02)
Activation parameters for the solvolysis in aqueous trifluoroethanol of arenesulphonyl chlorides with electron-supplying substituents have been determined; the results are not in accord with earlier proposals that such compounds reacts by an SN1 mechanism.
Limitations of the Transition State Variation Model. Part 2. Dual Reaction Channels for Solvolyses of 2,4,6-Trimethylbenzenesulphonyl Chloride
Koo, In Sun,Bentley, T. William,Kang, Dae Ho,Lee, Ikchoon
, p. 175 - 179 (2007/10/02)
Rate constants for solvolyses of 2,4,6-trimethylbenzenesulphonyl chloride (1) are reported for aqueous binary mixtures with acetone, acetonitrile, dioxane, ethanol and methanol.Kinetic solvent isotope effects in water and in methanol and product selectivities in alcohol-water mixtures are also reported.Additional YCl values have been determined for aqueous acetonitrile and dioxane from rate constants for solvolyses of 1-adamantane chloride.Contrary to earlier reports, correlations between logarithms of rate constants for solvolyses of 1 vs.Y or YCl are approximately bilinear.From these plots the rate data are dissected into contributions from two competing reaction channels, and this interpretation is supported for alcohol-water mixtures by the trends of product selectivities, which show maxima close to the solvent compositions where there are breaks in the rate-rate profiles.Greater rate constants for 40 percent v/v ethanol-water than for 97 percent w/w trifluoroethanol-water ( solvents of approximately equal ionizing power) show the importance of nucleophilic solvent assistance (SN2 character) even for the reaction channel favoured in more polar media.Hence, in agreement with an earlier consensus, neither of the reaction channels corresponds to an SN1 mechanism.From the kinetic solvent isotope effect of 1.68 in methanol, it is proposed that the reaction channel favoured in less polar media is general-base catalysed and/or is possibly an addition-elimination pathway.
