# Is a meta-sodium sulfonate group on a benzene ring electron withdrawing or donating?

I am wondering if a sodium sulfinate group would decrease or increase the electron density of the aromatic ring

• I'd say it is like carboxylate group, only worse. – Ivan Neretin May 29 '18 at 8:33
• I agree, the S is strongly d positive and that will draw electron density out of the ring. – Waylander May 29 '18 at 8:55
• – Gaurang Tandon Jun 29 '18 at 3:19
• @Gaurang not related. Adding another oxygen atom changes a lot of things. – Oscar Lanzi Aug 28 '18 at 16:38

As $\ce{SO3H}$ is a strongly electron withdrawing group, I'd say that $\ce{SO3Na}$ is basically the same, but to a slightly less extent. The reason for this is that being a group of highly electronegative atoms both groups have strong inductive electron withdrawing effects but they are both at donating electrons via conjugation (only possible from $\ce{S\bond{2}O}$ bond). This means that the sodium sulfonate group will decrease the electron density on the aromatic ring.