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Sulfonate
 
 
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A sulfonate is a salt or ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 of a sulfonic acid
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
. It contains the functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 R-SO2O-.

Sulfonate salts
Anions with the general formula RSO2O− are called sulfonates. They are the conjugate bases of sulfonic acid
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
s with formula RSO2OH. As sulfonic acids tend to be strong acid
Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
s, the corresponding sulfonates are weak bases
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
. Due to the stability of sulfonate anions, the cations of sulfonate salts such as scandium triflate have application as Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
s.

A classic organic reaction
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 for the preparation of sulfonates is that of alkyl halides with sulfites such as sodium sulfite
Sodium sulfite

Sodium sulfite is a soluble compound of sodium. It is a product of SulfurOxygen2 scrubbing, a part of the flue gas desulfurization process....
, first described by Adolph Strecker
Adolph Strecker

Adolph Strecker was a Germany chemist who is remembered primarily for his work with amino acids....
 in 1868 (Strecker sulfite alkylation).






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Encyclopedia


A sulfonate is a salt or ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
 of a sulfonic acid
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
. It contains the functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 R-SO2O-.

Sulfonate salts


Anions with the general formula RSO2O− are called sulfonates. They are the conjugate bases of sulfonic acid
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
s with formula RSO2OH. As sulfonic acids tend to be strong acid
Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
s, the corresponding sulfonates are weak bases
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
. Due to the stability of sulfonate anions, the cations of sulfonate salts such as scandium triflate have application as Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
s.

A classic organic reaction
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 for the preparation of sulfonates is that of alkyl halides with sulfites such as sodium sulfite
Sodium sulfite

Sodium sulfite is a soluble compound of sodium. It is a product of SulfurOxygen2 scrubbing, a part of the flue gas desulfurization process....
, first described by Adolph Strecker
Adolph Strecker

Adolph Strecker was a Germany chemist who is remembered primarily for his work with amino acids....
 in 1868 (Strecker sulfite alkylation). The general reaction is:

RX + M2SO3 ? RSO3M + MX

Iodide
Iodide

An iodide ion is an iodine with a −1 electric charge. Compounds with iodine in formal oxidation state −1 are called iodides. This can include ionic compounds such as caesium iodide or covalent compounds such as phosphorus triiodide....
 is used as a catalyst.

Sulfonic esters


Esters with the general formula R1SO2OR2 are as a category called sulfonic esters, with individual members of the category being named analogously to how ordinary carboxyl esters are named
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
. For example, if the R2 group is a methyl group and the R1 group is a trifluoromethyl group, the resulting compound is methyl trifluoromethanesulfonate.

Sulfonic esters are used as reagents in organic synthesis, chiefly because the RSO2O- group is a good leaving group
Leaving group

A leaving group in chemistry is an ion or substituent with the ability to detach itself from a molecule. The remaining molecule or fragment remaining is known as the residual or main part....
s in Sn1, Sn2, E1 and E2 reactions. Methyl_triflate
Methyl triflate

Methyl trifluoromethanesulfonate, is commonly called methyl triflate, and has the chemical formula CF3SO2-OCH3, and is used as a very powerful Methylation reagent in chemistry....
, for example, is a strong methylating reagent.

Examples


  • Mesylate
    Mesylate

    In chemistry, a mesylate is any salt or ester of methanesulfonic acid . In salts, the mesylate is present as the CH3SO3- anion....
     (methanesulfonate), CH3SO2O-
  • Triflate
    Triflate

    Triflate, more formally known as trifluoromethanesulfonate, is a functional group with the formula CF3SO3-. The triflate group is often represented by -OTf, as opposed to -Tf....
     (trifluoromethanesulfonate), CF3SO2O-
  • Tosylate
    Tosyl

    A tosyl group is CH3C6H4SO2. This group is usually derived from the compound 4-Toluenesulfonyl chloride, CH3C6H4SO2Cl, which forms esters and amides of toluenesulfonic acid....
     (p-toluenesulfonate), CH3C6H4SO2O-
  • Besylate (benzenesulfonate), C6H5SO2O-


See also


  • Sulfate
    Sulfate

    In inorganic chemistry, a sulfate is a salt of sulfuric acid....
  • Sulfoxide
    Sulfoxide

    A sulfoxide is a chemical compound containing a sulfinyl functional group attached to two carbon atoms. Sulfoxides can be considered as oxidized thioether....
  • Sulfonyl
    Sulfonyl

    A sulfonyl group is an organic radical or functional group obtained from a sulfonic acid by the removal of the hydroxyl group. Sulfonyl groups can be written as having the general formula R-S2-R', where there are two double bonds between the sulfur and oxygen....
  • Sulfoxyl