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Topic: which will be the less polar : allyl amine of tosylated allyl amine?  (Read 3590 times)

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Offline faust

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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



« Last Edit: October 23, 2005, 04:21:36 AM by Mitch »

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Re:which will be the less polar : allyl amine of tosylated allyl amine?
« Reply #1 on: October 23, 2005, 04:40:26 PM »
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.

Offline faust

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Re:which will be the less polar : allyl amine of tosylated allyl amine?
« Reply #2 on: October 26, 2005, 01:09:04 AM »
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...

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Re:which will be the less polar : allyl amine of tosylated allyl amine?
« Reply #3 on: October 26, 2005, 01:57:59 PM »
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.

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