ORGLIST:Is the sulphonate group activating?

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From: antonio regla (areglac$##$yahoo.com)
Date: Tue Feb 18 2003 - 15:29:35 EST

Dear List members:

I would like to ask any of you if the sulfonate group on an aryl halide is activating towards nucleophilic aromatic substitution, or if it is the sulfonic acid group the one activating?. Books such as Morrison and Boyd list the sulfonic acid group, SO3H, as an activating group in nucleophilic aromatic substitutions, but it doesn't say anything about the sulfonate group (SO3Na). I have been trying to displace chlorine in the presence of a sulfonate group, and the reaction just doesn't go on it, and I am quite puzzled about it. If you have any ideas on this topic, please share them with me, I will appreciate them.

Sincerely,

Antonio Regla

Facultad de Farmacia, U.A.E.M. Cuernavaca, Mexico

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