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Topic: Polarity of azide group (N3).  (Read 14463 times)

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Offline peptideismylife

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Polarity of azide group (N3).
« on: June 29, 2011, 07:20:09 PM »
Hi,

I was wondering about the polarity of azide group. I know the aminogroup is a very good polar group but what about azide group? has it weakly polarity?

Offline Sepelio

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Re: Polarity of azide group (N3).
« Reply #1 on: June 29, 2011, 07:41:26 PM »
The azide does have polarity. If you look at the resonance structure you can push electrons around and see it. The wiki page actually has some decent diagrams on it:
http://en.wikipedia.org/wiki/Azide

Offline discodermolide

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Re: Polarity of azide group (N3).
« Reply #2 on: June 29, 2011, 11:57:14 PM »
Hi,

I was wondering about the polarity of azide group. I know the aminogroup is a very good polar group but what about azide group? has it weakly polarity?

Are you talking about chromatographic polarity? If so it is less polar than the amino group.
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Offline Honclbrif

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Re: Polarity of azide group (N3).
« Reply #3 on: June 30, 2011, 08:23:00 AM »
I've done bromide to azide swaps and seen almost no change in Rf, even by HPLC.
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Offline discodermolide

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Re: Polarity of azide group (N3).
« Reply #4 on: June 30, 2011, 08:29:31 AM »
I've done bromide to azide swaps and seen almost no change in Rf, even by HPLC.

Sure, I agree,  but amino to azide is a big difference in chromatographic polarity
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