[faust]

Hello,

I know it's maybe a stupid question... but.. on a TLC plate, which will be the less polar : allyl amine of tosylated allyl amine?

Thanks

[movies]

What would you expect the trend to be as you progressed from a primary amine to a secondary and then a tertiary amine?  Think in terms of the availibility of hydrogens and lone pairs for hydrogen bonding or other polar interactions.

[faust]

I tought that the tertiary amine will be the more polar simple because It's the more nucleophilic indeed it have 3 donnating groups (3 alkyls)

But the NMR says the opposite

the secondary amine is the more polar...

[movies]

True, a tertiary amine will have a more electron rich nitrogen, however you have to also account for the difference in how accessible that nitrogen is.

Also, a tosyl group is an electron withdrawing group through resonance.