Sulfonate
Overview
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
of a sulfonic acid
Sulfonic acid
Sulfonic acid usually refers to a member of the class of organosulfur compounds with the general formula RS2–OH, where R is an alkyl or aryl. The formal part of acid, HS2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2.-Preparation:Sulfonic acid is...
. 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. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
R-SO2O-.
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 organosulfur compounds with the general formula RS2–OH, where R is an alkyl or aryl. The formal part of acid, HS2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2.-Preparation:Sulfonic acid is...
s with formula RSO2OH. As sulfonic acids tend to be strong acid
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
s, the corresponding sulfonates are weak bases
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
. Due to the stability of sulfonate anions, the cations of sulfonate salts such as scandium triflate have application as Lewis acid
Lewis acid
]The term Lewis acid refers to a definition of acid published by Gilbert N. Lewis in 1923, specifically: An acid substance is one which can employ a lone pair from another molecule in completing the stable group of one of its own atoms. Thus, H+ is a Lewis acid, since it can accept a lone pair,...
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, photochemical reactions and redox reactions. In organic synthesis,...
for the preparation of sulfonates is that of alkyl halides with sulfites such as sodium sulfite
Sodium sulfite
Sodium sulfite is a soluble sodium salt of sulfurous acid. It is a product of sulfur dioxide scrubbing, a part of the flue gas desulfurization process...
, first described by Adolph Strecker
Adolph Strecker
Adolph Strecker was a German chemist who is remembered primarily for his work with amino acids.- Life and work :...
in 1868 (Strecker sulfite alkylation).
Unanswered Questions
