[thedy]

Hi,I have one question.
Can negative charge of carboxylate group be stabilized by involving to the benzene ring?
Like here: https://docs.google.com/drawings/d/1B7CAXUEJ8Grs3Ci8W_GfvLPB8nD4QjoxMe4J7ktI9e0/edit?hl=sk&pli=1

I have read in one article,that this charge cannot be involved to the ring,because this charge is insulated from ring by presence of two single bonds.But there is alternating sigma and pi bond,isnt there?

Please,try explain me,where I am wrong with charge of patient.Thanks a lot...

[Schrödinger]

This negative charge on the carboxylate oxygen is 2 single bonds away from the benzene ring. But conjugation ALWAYS occurs when they are separated by one single bond.

Your structure is like -C=C-C-O^-

Had it been -C=C-O^-, then the negative charge could have stepped down from the O atom the double bond could have migrated(cleaved) to form a negative charge on the left C atom.

But this is not the case with our benzoic acid.

[thedy]

This negative charge on the carboxylate oxygen is 2 single bonds away from the benzene ring. But conjugation ALWAYS occurs when they are separated by one single bond.

Your structure is like -C=C-C-O^-

Had it been -C=C-O^-, then the negative charge could have stepped down from the O atom the double bond could have migrated(cleaved) to form a negative charge on the left C atom.

But this is not the case with our benzoic acid.

And what about double bond between oxygen and carbon in COOH?Can this bond involve with ring?This double bond is separated with only one single bond,am I right?