Sulfonic acid halides

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General formula of the sulfonic acid halides (X = F, Cl, Br or I), sulfonic acid fluorides and sulfonic acid chlorides as well as the structural formulas of tosyl chloride and mesyl chloride (from top left to bottom right). R is the organyl radical (alkyl radical, aryl radical, alkylaryl radical et cetera). The halosulfonyl residue is marked in blue .

Sulphonic acid halides , also called sulphonyl halides, are a group of substances in organic chemistry . They contain a sulfonyl group , which has a single bond to a halogen - atom is bound. Its general formula is R-SO 2 -X, where X is halogen.

Sulfonic acid fluorides

Sulphonic acid fluorides, also called sulphonyl fluorides, have the general formula R – SO 2 –F and are used as starting materials in syntheses. Most of the industrially produced perfluorooctanesulfonyl derivatives, such as PFOS , are made from a sulfonic acid fluoride .

Sulfonic acid chlorides

Sulphonic acid chlorides, also called sulphonyl chlorides, have the general formula R – SO 2 –Cl. They react with nucleophiles such as alcohols , primary or secondary amines (see Hinsberg separation ). When the nucleophile is an alcohol, a sulfonic acid ester is formed . If the nucleophile is an amine, a sulfonamide is formed. Important sulfonic acid chlorides are tosyl chloride , brosyl chloride , Nosylchlorid and mesyl . The sulfonic acid chlorides are usually synthesized via the Reed reaction . Sulphonic acid chlorides are sensitive to moisture.

Individual evidence

  1. ↑ Hans-Joachim Lehmler: Synthesis of environmentally relevant fluorinated surfactants - a review . In: Chemosphere . tape 58 , no. 11 , March 1, 2005, p. 1471-1496 , doi : 10.1016 / j.chemosphere.2004.11.078 , PMID 15694468 .
  2. ^ Hans Beyer , Wolfgang Walter : Organic chemistry. S. Hirzel Verlag, Stuttgart 1984, pp. 458-459, ISBN 3-7776-0406-2 .
  3. ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 5: Pl-S. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1987, ISBN 3-440-04515-3 , p. 4054.
  4. ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 5: Pl-S. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1987, ISBN 3-440-04515-3 , p. 4050.