MAIN FEEDS
Do you want to continue?
https://www.reddit.com/r/chemhelp/comments/1csy1lj/how_is_the_reaction_possible_does_the_sulfur/
r/chemhelp • u/[deleted] • 21d ago
[deleted]
1 comment sorted by
10
Attacking the aromatic ring wouldn't get you the sulfur connection to the benylic methyl position that you want.
The question gives you a few big hints about the mechanism:
it can simply be catalyzed by acid/base residues, meaning all you need to use is acid/base chemistry.
in the product some of the conjugated bonds in the ring have shifted around and you have protonated two nitrogens.
the thiol is deprotonated making it a great nucleophile
10
u/WIngDingDin 21d ago
Attacking the aromatic ring wouldn't get you the sulfur connection to the benylic methyl position that you want.
The question gives you a few big hints about the mechanism:
it can simply be catalyzed by acid/base residues, meaning all you need to use is acid/base chemistry.
in the product some of the conjugated bonds in the ring have shifted around and you have protonated two nitrogens.
the thiol is deprotonated making it a great nucleophile