Re: ORGLIST: deuterium exchange

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From: Manuel Toennis (Manuel.Toennis$##$ch.tum.de)
Date: Wed Apr 28 1999 - 01:55:09 EDT

Merlin wrote:
>
> I actually posted a similar query on a similar matter a little while
> ago. To the best of my knowledge, the dielectric constant and
> polarizability seem to indicate a possibility for CH3CN to perform such
> a transformation, but I'm not going to say for 100% certainty that it
> will occur.


Acetonitrile is somewhat acidic due to to strong electron withdrawing
effect of the cyano group stabilizing the anion. The pKs could be around
12, couldn't find it exactly right now. So a deprotonation /
reprotonation is likely.
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