[Violet]

Hi, I'm a little confused about the nucleophilicity of indole:
Is it a harder nucleophile at N1 or C3? And is disulfide a softe or hard electrophile? If they react with each other, will the N1 or C3 attack the sulfur in disulfide?

Thanks a lot!

[Smrt guy]

The N should be harder than the C (it is smaller and has greater charge density).  S is soft; as a nucleophile and as an electrophile (it is large and polarizable).

[Violet]

The N should be harder than the C (it is smaller and has greater charge density).  S is soft; as a nucleophile and as an electrophile (it is large and polarizable).

Thank you, so if I put them in an aqeous solution, will the disulfide still react more possibly with C3 than N1?

[Smrt guy]

I don't know how reactive disulfides are, but if it reacts I suspect that C3 would react faster than N.

[Violet]

I don't know how reactive disulfides are, but if it reacts I suspect that C3 would react faster than N.

Thanks, that's also what I think.