Sulfinic Acid
   HOME
*



picture info

Sulfinic Acid
Sulfinic acids are oxoacids of sulfur with the structure RSO(OH). In these organosulfur compounds, sulfur is pyramidal. Structure and properties Sulfinic acids RSO2H are about 1000x more acidic than the corresponding carboxylic acid RCO2H. Sulfur is pyramidal, consequently sulfinic acids are chiral. Preparation They are often prepared in situ by acidification of the corresponding sulfinate salts, which are typically more robust than the acid. These salts are generated by reduction of sulfonyl chlorides. An alternative route is the reaction of Grignard reagents with sulfur dioxide. Transition metal sulfinates are also generated by insertion of sulfur dioxide into metal alkyls, a reaction that may proceed via a metal sulfur dioxide complex. Unsubstituted sulfinic acid, when R is the hydrogen atom, is a higher energy isomer of sulfoxylic acid, both of which are unstable. Examples An example of a simple, well-studied sulfinic acid is phenylsulfinic acid. A commercially import ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Rongalite
Rongalite is a chemical compound with the molecular formula Na+HOCH2SO2−. This salt has many additional names, including Rongalit, sodium hydroxymethylsulfinate, sodium formaldehyde sulfoxylate, and Bruggolite. It is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI). It is water-soluble and generally sold as the dihydrate. The compound and its derivatives are widely used in the dye industry.D. Schubart "Sulfinic Acids and Derivatives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2012, Wiley-VCH, Weinheim. The structure of this salt has been confirmed by X-ray crystallography. Synthesis and reactions Although available commercially, the salt can be prepared from sodium dithionite and formaldehyde: :Na2S2O4 + 2 CH2O + H2O → HO-CH2-SO3Na + HO-CH2-SO2Na This reaction proceeds quantitatively, such that dithionite can be determined by its conversion to Rongalite, which is far less O2-sensitive and thus easier to handle. The ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Sultine
In chemistry, a sultine is a cyclic ester of a sulfinic acid. This class of organosulfur compounds has few applications. These compounds are typically prepared by the dehydration of hydroxy-sulfinic acids or their equivalent. Illustrative of an alternative route, xylylene dibromide reacts with sodium sulfoxylate (source of SO22-) to give the sultine C6H4(CH2S(O)OCH2), which is a precursor to o-quinodimethane In organic chemistry, a xylylene (sometimes quinone-dimethide) is any of the constitutional isomers having the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms ....{{cite book, first1=Donald C., last1=Dittmer, first2=Michael D., last2=Hoey , chapter=Cyclic Sulphinic Acid Derivatives (Sultines and Sulphinamides), page = 239-273, year=1981, editor=Saul Patai, title=Sulphinic Acids, Esters and Derivatives, doi=10.1002/9780470772270.ch9, publisher=John Wiley & Sons, series=PATAI'S Chemistr ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Cysteine
Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometimes the symbol Cyz is used. The deprotonated form can generally be described by the symbol Cym as well. The thiol is susceptible to oxidation to give the disulfide derivative cystine, which serves an important structural role in many proteins. In this case, the symbol Cyx is sometimes used. When used as a food additive, it has the E number E920. Cysteine is encoded by the codons UGU and UGC. The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids. Structure Like other amino acids (not as a residue of a protein), cysteine exists as a zwitterion. Cysteine has chirality in the older / notation based on homology to - and -glyceraldehyde. In the newer ''R''/''S'' system of designating chi ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Cysteine Dioxygenase
Cysteine dioxygenase (CDO) is a non-heme iron enzyme that catalyzes the conversion of L-cysteine to cysteine sulfinic acid (cysteine sulfinate). CDO plays an important role in cysteine catabolism, regulating intracellular levels of cysteine and responding changes in cysteine availability. As such, CDO is highly regulated and undergoes large changes in concentration and efficiency. It oxidizes cysteine to the corresponding sulfinic acid by activation of dioxygen, although the exact mechanism of the reaction is still unclear. In addition to being found in mammals, CDO also exists in some yeast and bacteria, although the exact function is still unknown. CDO has been implicated in various Neurodegeneration, neurodegenerative diseases and cancers, which is likely related to cysteine toxicity. Function CDO is responsible for the first major step in metabolism of cysteine. CDO oxidizes to cysteine sulfinic acid (which exists predominantly in the anionic sulfinate form ''in vivo''). Overa ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Conjugate Base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a hydrogen ion. On the other hand, a conjugate base is what is left over after an acid has donated a proton during a chemical reaction. Hence, a conjugate base is a species formed by the removal of a proton from an acid, as in the reverse reaction it is able to gain a hydrogen ion. Because some acids are capable of releasing multiple protons, the conjugate base of an acid may itself be acidic. In summary, this can be represented as the following chemical reaction: :acid + base conjugate\ base + conjugate\ acid Johannes Nicolaus Brønsted and Martin Lowry introduced the Brønsted–Lowry theory, which proposed that any compound that can transfer a proton to any other compound is an acid, and the compound that accepts the proton is a b ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Hydrogen Peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%–6% by weight) in water for consumer use, and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or " high-test peroxide", decomposes explosively when heated and has been used as a propellant in rocketry. Hydrogen peroxide is a reactive oxygen species and the simplest peroxide, a compound having an oxygen–oxygen single bond. It decomposes slowly when exposed to light, and rapidly in the presence of organic or reactive compounds. It is typically stored with a stabilizer in a weakly acidic solution in a dark bottle to block light. Hydrogen peroxide is found in biological systems including the human body. Enzymes that use or decompose hydrogen peroxide are classified as peroxidases. Properties The boiling poi ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. There are two classes of redox reactions: * ''Electron-transfer'' – Only one (usually) electron flows from the reducing agent to the oxidant. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * ''Atom transfer'' – An atom transfers from one substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously the oxidation state of oxygen decreases as it accepts electrons released by the iron. Although oxidation reactions are commonly associated with the formation of oxides, other chemical species can serve the same function. In hydrogenation, C=C (and other) bonds ar ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Phenylsulfinic Acid
Phenylsulfinic acid is an organosulfur compound with the formula C6H5SO2H. It is a colorless or white crystalline solid that is usually stored in the form of its sodium salt. In aqueous solution it is strongly acidic and is easily oxidized in air. Phenylsulfinic acid and its esters are chiral. Acidity There is a large range of p''K''a values in the literature, with most authors giving a value of around 1.30.a) A. T. Fuller, I. M. Tonkin and J. Walker, J. Chem. Soc., 1945, 636; b) S. Smiles and C. M. Bere, "Organic Syntheses," Coll. Vol. I, ed. by A. H. Blatt, John Wiley and Sons, Inc., New York, 1948, p. 7; c) E. Bader and H. D. Hermann, Chem. Ber., 88, 46 (1955); d) M. Kulka, Can. J. Chem., 32, 601 (1954). This inconsistency can be explained by differences in ionic strength between quoted values. By measuring the p''K''a at various ionic strengths and extrapolating to zero ionic strength, the p''K''a of phenylsulfinic acid was determined to be 2.76. This ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Hypotaurine
Hypotaurine is a sulfinic acid that is an intermediate in the biosynthesis of taurine. Like taurine, it also acts as an endogenous neurotransmitter via action on the glycine receptors. It is an osmolyte with antioxidant properties. Hypotaurine is derived from cysteine (and homocysteine). In mammals, the biosynthesis of hypotaurine from cysteine occurs in the pancreas. In the cysteine sulfinic acid pathway, cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine dioxygenase Cysteine dioxygenase (CDO) is a non-heme iron enzyme that catalyzes the conversion of L-cysteine to cysteine sulfinic acid (cysteine sulfinate). CDO plays an important role in cysteine catabolism, regulating intracellular levels of cysteine and res .... Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine. Hypotaurine is enzymatically oxidized to yield taurine by hypotaurine dehydrogenase. References Amines Sulfinic acids ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  




Oxoacid
An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce the H+ cation and the anion of the acid. Description Under Lavoisier's original theory, all acids contained oxygen, which was named from the Greek ὀξύς (''oxys'': acid, sharp) and the root -γενής (''-genes'': creator). It was later discovered that some acids, notably hydrochloric acid, did not contain oxygen and so acids were divided into oxo-acids and these new hydroacids. All oxyacids have the acidic hydrogen bound to an oxygen atom, so bond strength (length) is not a factor, as it is with binary nonmetal hydrides. Rather, the electronegativity of the central atom and the number of oxygen atoms determine oxyacid acidity. For oxyacids with the same central atom, acid strength increases with the number of oxygen atoms attache ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Thiourea Dioxide
Thiourea dioxide or thiox is an organosulfur compound that is used in the textile industry. It functions as a reducing agent. It is a white solid, and exhibits tautomerism. Structure The structure of thiourea dioxide depends on its environment. Crystalline and gaseous thiourea dioxide adopts a structure with C2v symmetry. Selected bond lengths: S-C = 186, C-N = 130, and S-O = 149 pm. The sulfur center is pyramidal. The C-S bond length is more similar to that of a single bond. For comparison, the C=S bond in thiourea is 171 pm. The long C-S bond indicates the absence of C=S character. Instead the bonding is described with a significant contribution from a dipolar resonance structure with multiple bonding between C and N. One consequence of this bonding is the planarity of the nitrogen centers. In the presence of water or DMSO, thiourea dioxide converts to the tautomer, a sulfinic acid, (H2N)HN=CS(O)(OH), named formamidine sulfinic acid. Synthesis Thiourea dioxide was first prepare ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]