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The sulfonate ion. In organosulfur chemistry, a sulfonate is a salt, anion or ester of a sulfonic acid. Its formula is R−S(=O) 2 −O −, containing the functional group −S(=O) 2 −O −, where R is typically an organyl group, amino group or a halogen atom. Sulfonates are the conjugate bases of sulfonic acids.
The requirement for a good leaving group is relaxed in conjugate base elimination reactions. These reactions include loss of a leaving group in the β position of an enolate as well as the regeneration of a carbonyl group from the tetrahedral intermediate in nucleophilic acyl substitution.
On the other hand, if a chemical is a weak acid its conjugate base will not necessarily be strong. Consider that ethanoate, the conjugate base of ethanoic acid, has a base splitting constant (Kb) of about 5.6 × 10 −10, making it a weak base. In order for a species to have a strong conjugate base it has to be a very weak acid, like water.
Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C 6 H 6 O 3 S.It is the simplest aromatic sulfonic acid.It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether.
In these reactions, the conjugate acid of the carbonyl group is a better electrophile than the neutral carbonyl group itself. Depending on the chemical species that act as the acid or base, catalytic mechanisms can be classified as either specific catalysis and general catalysis. Many enzymes operate by general catalysis.
Leaving group reactivity of alcohols can be increased with sulfonates, such as tosylate (− OTs), triflate (− OTf), and mesylate (− OMs). Poor leaving groups include hydroxide (− OH), alkoxides (− OR), and amides (− NR 2). The Finkelstein reaction is one S N 2 reaction in which the leaving group can also act as a nucleophile. In this ...
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Secondly, the conjugate base of a strong acid is not a weak base, it is not a base at all, but rather neutral (e.g. the halide ion from strong hydrohalic acids, or the nitrate ion). I am not sure if it is even worth mentioning in this article about the relationship between acids and bases, it seems simpler to me to just note that sulfonates are ...