sulfinic acid

スルフィン酸

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/09 06:32:46」(JST)

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The general structure of a sulfinic acid

Sulfinic acids are oxoacids of sulfur with the structure RSO(OH). In these organosulfur compounds, sulfur is pyramidal.

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.^[1] 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.

Examples

An example of a simple, well-studied sulfinic acid is phenylsulfinic acid. A commercially important sulfinic acid is thiourea dioxide, which is prepared by the oxidation of thiourea with hydrogen peroxide.^[2]

(NH₂)₂CS + 2H₂O₂ → (NH)(NH₂)CSO₂H + 2H₂O

Structure of "thiourea dioxide", a commercially useful sulfinic acid.

Another commercially important sulfinic acid is hydroxymethyl sulfinic acid, which is usually employed as its sodium salt (HOCH₂SO₂Na). Called Rongalite, this anion is also commercially useful as a reducing agent.

Sulfinite

The conjugate base of a sulfinic acid is a sulfinite anion. The enzyme cysteine dioxygenase converts cysteine into the corresponding sulfinite. One product of this catabolic reaction is the sulfinic acid derivative hypotaurine.

References

^ Whitmore, F. C.; Hamilton, F. H. (1941). "Sodium p-Toluenesulfinic acid". Org. Synth. ; Coll. Vol. 1, p. 492
^ D. Schubart "Sulfinic Acids and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a25_461

External links

Sulfinic Acids at the US National Library of Medicine Medical Subject Headings (MeSH)
Diagram at ucalgary.ca
Diagram at acdlabs.com

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English Journal

ROSics: Chemistry and proteomics of cysteine modifications in redox biology.

Kim HJ1, Ha S, Lee HY, Lee KJ.
Mass spectrometry reviews.Mass Spectrom Rev.2015 Apr;34(2):184-208. doi: 10.1002/mas.21430. Epub 2014 Jun 10.
Post-translational modifications (PTMs) occurring in proteins determine their functions and regulations. Proteomic tools are available to identify PTMs and have proved invaluable to expanding the inventory of these tools of nature that hold the keys to biological processes. Cysteine (Cys), the least
PMID 24916017

Cysteine dioxygenase and cysteine sulfinate decarboxylase genes of the deep-sea mussel Bathymodiolus septemdierum: possible involvement in hypotaurine synthesis and adaptation to hydrogen sulfide.

Nagasaki T1, Hongo Y, Koito T, Nakamura-Kusakabe I, Shimamura S, Takaki Y, Yoshida T, Maruyama T, Inoue K.
Amino acids.Amino Acids.2015 Mar;47(3):571-8. doi: 10.1007/s00726-014-1891-z. Epub 2014 Dec 16.
It has been suggested that invertebrates inhabiting deep-sea hydrothermal vent areas use the sulfinic acid hypotaurine, a precursor of taurine, to protect against the toxicity of hydrogen sulfide contained in the seawater from the vent. In this protective system, hypotaurine is accumulated in the gi
PMID 25501502

One-Pot Synthesis of Aryl Sulfones from Organometallic Reagents and Iodonium Salts.

Margraf N1, Manolikakes G.
The Journal of organic chemistry.J Org Chem.2015 Feb 17. [Epub ahead of print]
A transition-metal-free arylation of lithium, magnesium, and zinc sulfinates with diaryliodonium salts is described. The sulfinic acid salts were prepared from the reaction of the corresponding organometallic reagents and sulfur dioxide. Combination of the three single steps (preparation of the orga
PMID 25650485

Japanese Journal

Catalytic Mechanism of Nitrile Hydratase Proposed by Time-resolved X-ray Crystallography Using a Novel Substrate, tert-Butylisonitrile

Hashimoto Koichi,Suzuki Hiroyuki,Taniguchi Kayoko,Noguchi Takumi,Yohda Masafumi,Odaka Masafumi,野口巧
The journal of biological chemistry 283(52), 36617-36623, 2008-12
… Nitrile hydratases (NHases) have an unusual iron or cobalt catalytic center with two oxidized cysteine ligands, cysteine-sulfinic acid and cysteine-sulfenic acid, catalyzing the hydration of nitriles to amides. …
NAID 120001046916

Synthesis and alkylation of sodium 4-thioxo-1,4-dihydroquinoline-3-sulfinate

Skrzypek Leszek,Maslankiewicz Andrzej
Heterocycles 75(11), 2769-2778, 2008-11-01
NAID 40016301259

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