Sulfonic acid

Summary

In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula , where R is an organic alkyl or aryl group and the group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, , a tautomer of sulfurous acid, . Salts or esters of sulfonic acids are called sulfonates. Preparation Aryl sulfonic acids are produced by the process of sulfonation. Usually the sulfonating agent is sulfur trioxide. A large scale application of this method is the production of alkylbenzenesulfonic acids: :RC6H5 + SO3 -> RC6H4SO3H In this reaction, sulfur trioxide is an electrophile and the arene is the nucleophile. The reaction is an example of electrophilic aromatic substitution.

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Chemical biology is a key discipline in biomedical research for drug discovery, synthetic biology and protein functional annotation. We will give a broad perspective of the field ranging from seminal classical experiments to state-of-the-art approaches to dissect and perturb biological systems.

L'objectif de ce cours est de fournir les connaissances et le moyen de comprendre, au niveau moléculaire, le fonctionnement des réactions chimiques organiques. Pendant le cours, l'étudiant réfléchira et résoudra de nouveaux problèmes.

Acquisition des notions fondamentales liées à la réactivité des molécules organiques, identification de la structure de petites molécules organiques au moyen des techniques de spectrométrie de masse, spectroscopie infra-rouge et résonance magnétique nucléaire.

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The goal of this thesis was to open a new route to the synthesis of conjugated trienes using a new SO2-based C-C bond forming reactions developed in Lausanne. In addition, the potential of SO2 for applications in synthetic organic chemistry has been exploited. Firstly, we discovered that under suitable conditions sulfur dioxide is able to undergo ene reaction with different building blocks such as enoxysilanes and allylsilanes to form the corresponding sulfinates. The latter can be used as key intermediates for the preparation of β-ketones, β-keto-sulfonamides and β-keto-sulfonic esters. This approach allows preparing β-keto-sulfonamides in one-pot operations. Up to now, the same type of compounds would require multi-steps syntheses. Considering the importance of sulfonamides and sulfonic esters in medicinal chemistry we prepared representative examples of such compounds. Secondly, our studies demonstrate, for the first time, that sulfones containing (E)-alkene units can be obtained through the reaction of (E,E)-1-silyloxy-2-methylpenta-1,3-diene with substituted enoxysilanes and an excess of sulfur dioxide, followed by subsequent quenching with electrophiles. Importantly, this four-component reaction yields (E)-alkenes only in the presence of a protic acid promoter and only with 1-silyloxypentadienes. In all cases mixtures of α,β-syn and α,β-anti ketones are obtained. The α,β-diastereoselectivity of the oxyallylation (face selectivity of the enoxysilane addition) does not surpass 6:1 (3R,4S vs.3S,4S). Interestingly only β,ε-like substituted ε-sulfonylketones are formed, in contrast with the (Z)-isomers which present unlike β,ε-relative configuration. Thirdly, sulfur dioxide-based chemistry was applied for the asymmetric synthesis of the conjugated (E,E,E)-triene moiety of apoptolidinone, a highly potent apoptosis inducing agent with a daunting molecular architecture. Two main synthetic routes towards the synthesis of the trienic fragment of apoptolidinone were developed, one leading to the racemic fragment and a second route leading to the enantiomerically enriched C(1)-C(9) fragment. The latter was transformed further into the fragment already synthesized by Nicolaou and co-workers, demonstrating that this second route is significantly shorter than the route previously reported in the literature. The same methodology yields also facile access to the trienic part C(5)-C(14) fragment of restricticin. This underlines further the general applicability and the high flexibilities of our method toward the synthesis of trienes.

EPFL2004

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The reactivity of stable tertiary enamides in nucleophilic addition reaction with various in-situ generated imines was explored. Under very mild conditions, formyl-bearing tertiary enamides reacted with both aromatic and aliphatic amines to form imine intermediates. In the absence or presence of p-toluenesulfonic acid as a catalyst, intramolecular nucleophilic addition of enamide to imine functionality proceeded effectively to produce diverse 4-amino-1,2,3,4-tetrahydropyridine derivatives in good to excellent yields.

Elsevier2012

Ultraviolet Filtration Passivator for Stable High-Efficiency Perovskite Solar Cells

Keith Gregory Brooks, Mohammad Khaja Nazeeruddin, Yi Zhang, Bing Zhang

Although the published values of power conversion efficiency (PCE) have increased continuously in recent years for perovskite solar cells (PSCs), improvements in the stability and performance of PSCs with conventional TiO2 or SnO2 electron transport layers (ETLs) remain limited by the presence of nonideal interface defects and low ultraviolet (UV) absorption. In this study, 2-hydroxy-4-methoxy-5-sulfonate-benzophenone (SBP), an inexpensive water-soluble sunscreen raw material, was incorporated into the SnO2 ETL as a UV filter. It was found that the exposure of perovskite to UV light was significantly reduced, and, more importantly, the carbonyl and sulfonic acid groups in the SBP influenced both the perovskite crystallization process and the passivation of defects in the ETL/perovskite film interface. As a result, the PCE of SBP-based devices was increased to 22.54% from 20.78% of the control sample, with a concomitant decrease in the hysteresis. Moreover, the efficiency of champion devices with SBP decreased by less than 5% after 200 h of continuous UV (1.63 mW/cm2, 285 nm) irradiation, while the control group dropped to below 75% of the initial value, thus showing significantly improved stability.

AMER CHEMICAL SOC2022

EPFL2004