September 23, 2019, 06:05:57 AM
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Topic: Hydrogen-deuterium exchange  (Read 199 times)

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Offline Urbanium

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Hydrogen-deuterium exchange
« on: September 02, 2019, 09:00:45 AM »
How likely it is a H/D exchange will take place in a basic aqueous solution if the dissolved deuterated compound contains deuteriums only at alkyl groups (i.e. -CD3, -CD2-, -CD--)? I'm familiar with exchange at -OH and -NH groups, but does that occur with deuterated alkyl groups?

Offline Babcock_Hall

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Re: Hydrogen-deuterium exchange
« Reply #1 on: September 02, 2019, 09:47:14 AM »
Is there a functional group next to the carbon in question?

Offline Urbanium

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Re: Hydrogen-deuterium exchange
« Reply #2 on: September 02, 2019, 10:13:02 AM »
Is there a functional group next to the carbon in question?

There are hydroxyl groups only, more precisely a --CD-OH  and also one -CD2-OH further away.

Offline Babcock_Hall

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Re: Hydrogen-deuterium exchange
« Reply #3 on: September 02, 2019, 10:21:23 AM »
When a ketone group is in the alpha position relative to a -CHx group of some kind, basic exchange is expected.  Do you think that a hydroxyl group would have the same effect?  Why or why not?

Offline hollytara

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Re: Hydrogen-deuterium exchange
« Reply #4 on: September 02, 2019, 12:22:24 PM »
Carbonyls can undergo acid catalyzed exchange too. 

What is the pKa of the protons next to a hydroxyl?

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