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Organosulfur chemistry

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Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two (cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur.

Organic compoundOrganic compoundOrganic compounds are a subclass of chemical compounds of carbon. Little consensus exists among chemists on the exact definition of organic compound; the only universally accepted definition is the quasi-tautological "organic compounds are the subject matter of organic chemistry". Generally, any large chemical compound containing a carbon–hydrogen or carbon–carbon bond is accepted as an organic compound.SulfurSulfurChemical element with atomic number 16 (S)O↑S↓Sephosphorus ← sulfur → chlorineCysteineCysteineNames IUPAC nameCysteineSystematic IUPAC name2-Amino-3-sulfanylpropanoic acidOther names 2-Amino-3-sulfhydrylpropanoic acid2-Amino-3-mercaptopropanoic acidIdentifiers CAS Number52-90-452-89-1 (hydrochloride)921-01-7 D-cysteine3D model (JSmol)Interactive imageZwitterion: Interactive imageAbbreviations Cys, C ChEBICHEBI:15356ChEMBLChEMBL54943ChemSpider574 (Racemic)5653 (L-form)ECHA InfoCard100.000.145EC Number200-158-2E numberE920 (glazing agents, ...)IUPHAR/BPS4782KEGGD00026PubChemCID5862UNIIK848JZ4886A9U1687S1S (hydrochloride)CompTox Dashboard(EPA)DTXSID8022876InChIInChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)Key: XUJNEKJLAYXESH-UHFFFAOYSA-NInChI=1/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1Key: XUJNEKJLAYXESH-REOHCLBHBUInChI=1/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)Key: XUJNEKJLAYXESH-UHFFFAOYACSMILESC([C@@H](C(=O)O)N)SZwitterion: C([C@@H](C(=O)[O-])[NH3+])SProperties Chemical formulaC3H7NO2SMolar mass121.15 g·mol Appearance white crystals or powder Melting point240 °C (464 °F; 513 K) decomposes Solubility in water277g/L (at 25 °C) Solubility1.5g/100g ethanol 19 °C Acidity (pKa) 1.71 (conjugate acid), 8.33 (thiol), 10.78 Chiral rotation ([α]D)+9.4° (H2O, c = 1.3) Supplementary data page Cysteine (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Nverify ( ?)PenicillinPenicillinPenicillins (P, PCN or PEN) are a group of β-lactam antibiotics originally obtained from Penicilliummoulds, principally P. chrysogenum and P. rubens. Eight species of Penicillium, in the section Chrysogena, produce penicillins. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified.MethionineMethionineNames IUPAC nameMethionineSystematic IUPAC name2-Amino-4-(methylsulfanyl)butanoic acidOther names 2-amino-4-(methylthio)butanoic acidAmino-γ-methylthiobutyric acidIdentifiers CAS NumberL: 63-68-3D/L: 59-51-8D: 348-67-43D model (JSmol)L: Interactive imageL Zwitterion: Interactive imageAbbreviations Met, M ChEBIL: CHEBI:16643D/L: CHEBI:16811D: CHEBI:16867ChEMBLL: ChEMBL42336ChemSpiderL: 5907D/L: 853D: 76512DrugBankL: DB00134ECHA InfoCard100.000.393EC NumberL: 200-432-1KEGGL: C00073PubChemCIDL: 6137D/L: 876D: 84815UNIIL: AE28F7PNPLD/L: 73JWT2K6T3D: 868496F25RCompTox Dashboard(EPA)L: DTXSID9020821InChIInChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1Key: FFEARJCKVFRZRR-BYPYZUCNSA-ND/L: Key: FFEARJCKVFRZRR-UHFFFAOYSA-ND: Key: FFEARJCKVFRZRR-SCSAIBSYSA-NSMILESL: CSCC[C@H](N)C(=O)OL Zwitterion: CSCC[C@H]([NH3+])C(=O)[O-]Properties Chemical formulaC5H11NO2SMolar mass149.21 g·mol Appearance White crystalline powder Density1.340 g/cm Melting point281 °C (538 °F; 554 K) decomposes Solubility in waterSoluble Acidity (pKa) 2.28 (carboxyl), 9.21 (amino) Pharmacology ATC codeV03AB26 (WHO) QA05BA90 (WHO), QG04BA90 (WHO) Supplementary data page Methionine (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Methionine (symbol Met or M) () is an essential amino acid in humans.CoalCoalCombustible sedimentary rock composed primarily of carbonCoal is a combustible black or brownish-black sedimentary rock, formed as layers called coal seams. Coal is mostly carbon with variable amounts of other elements, chiefly hydrogen, sulfur, oxygen, and nitrogen. It is a fossil fuel, formed when plants decay into peat which is converted into coal by the heat and pressure of deep burial over millions of years.SaccharinSaccharinSaccharin, also called saccharine, benzosulfimide, or E954, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a sultam that is about 500 times sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products, such as drinks, candies, baked goods, tobacco products, excipients, and for masking the bitter taste of some medicines.PetroleumPetroleumNaturally occurring combustible liquidA sample of petroleumPumpjack pumping an oil well near Lubbock, Texas, U.S.An oil refinery in Ahmadi Governorate in KuwaitPetroleum, also known as crude oil or simply oil, is a natural resource that appears as a yellowish-black liquid chemical mixture found in geological formations, consisting primarily of hydrocarbons.Amino acidAmino acidOrganic compounds containing amine and carboxylic groupsStructure of a typical L-alpha-amino acid in the "neutral" formAmino acids are organic compounds that contain both amino and carboxylic acidfunctional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 appear in the genetic code of life.Mustard gasMustard gasMustard gas or sulfur mustard are names commonly used for the organosulfur chemical compound bis(2-chloroethyl) sulfide, which has the chemical structure S(CH2CH2Cl)2, as well as other species. In the wider sense, compounds with the substituents −SCH2CH2X or −N(CH2CH2X)2 are known as sulfur mustards or nitrogen mustards, respectively, where X = Cl or Br. Such compounds are potent alkylating agents, making mustard gas acutely and severely toxic.Sulfonamide (medicine)Sulfonamide (medicine)Sulfonamide is a functional group (a part of a molecule) that is the basis of several groups of drugs, which are called sulphonamides, sulfa drugs or sulpha drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g., the anticonvulsantsultiame. The sulfonylureas and thiazide diuretics are newer drug groups based upon the antibacterial sulfonamides.Fossil fuelFossil fuelFuel formed naturally from dead plants and animalsThe 3 main fossil fuels (from top to bottom): natural gas, oil (petroleum), and coalFossil fuels share energyA fossil fuel is a flammable carbon compound- or hydrocarbon-containing material formed naturally in the Earth's crust from the buried remains of prehistoric organisms (animals, plants or microplanktons), a process that occurs within geological formations.

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