| 词条 | Dithiobenzoic acid |
| 释义 |
| ImageFile = PhCS2H.svg | ImageSize = 124 | ImageAlt = | IUPACName = Benzenecarbodithioic acid | OtherNames = |Section1={{Chembox Identifiers | CASNo = 121-68-6 | PubChem = 67141 | EC_number = 204-491-4 | ChemSpiderID = 60487 |InChI=1S/C7H6S2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) |InChIKey = ZGRWZUDBZZBJQB-UHFFFAOYSA-N | SMILES = C1=CC=C(C=C1)C(=S)S }} |Section2={{Chembox Properties | C=7|H=6|S=2 | MolarMass = | Appearance = yellow-brown solid | Density = | MeltingPt = | BoilingPt = | pKa = 1.92[1] | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Dithiobenzoic acid is the organosulfur compound with the formula C6H5CS2H. It is a dithiocarboxylic acid, an analogue of benzoic acid, but more acidic and deeply colored. Synthesis and reactionsIt can be prepared by sulfiding benzal chloride[2] or by the reaction of the Grignard reagent phenylmagnesium bromide with carbon disulfide, followed by acidification.[3] It is about 100x more acidic than benzoic acid. Its conjugate base, dithiobenzoate, undergoes S-alkylation to give dithiocarboxylate esters.[2] Similarly, dithiobenzoate reacts with "soft" metal salts to give complexes, e.g. Fe(S2CC6H5)3 and Ni(S2CC6H5)2. Chlorination of dithiobenzoic acid gives the thioacyl chloride C6H5C(S)Cl. References1. ^{{cite book|author=M. R. Crampton|page=402|chapter=Acidity and hydrogen-bonding|title=The Chemistry of the Thiol Group|editor= Saul Patai|year= 1974|publisher=John Wiley & Sons Ltd|place=Chichester}} 2. ^1 {{cite journal|journal=Org. Synth.|year=1962|volume=42|page=100|doi=10.15227/orgsyn.042.0100|authors=Frederick Kurzer, Alexander Lawson|title=Thiobenzoylthioglycolic Acid}} 3. ^{{cite journal|title=Ueber Carbithiosäuren. I. Arylcarbithiosäuren|trans-title=About Carbothioic Acids I. Arylcarbothioic Acids|pages=3219–3233|author=J. Houben|doi=10.1002/cber.190603903140|journal=Berichte der deutschen chemischen Gesellschaft|year=1906|volume=39|issue=3}} 4. ^{{cite journal|authors=Bonamico, M.; Dessy, G.; Fares, V.; Scaramuzza, L.|title=Structural Studies of Metal Complexes with Sulphur-Containing Bidentate Ligands. Part I. Crystal and Molecular Structures of Trimeric Bis-(dithiobenzoato)-nickel(II) and -palladium(II)|journal=Journal of the Chemical Society, Dalton Transactions|issue=21|year=1975|pages=2250–2255|doi=10.1039/DT9750002250}} 2 : Organic acids|Organosulfur compounds |
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