GreenD - 15-2-2013 at 15:40
A friend made the claim that the Nitrogen of a nitrile would be nucleophilic, like the oxygen of a carboxylic acid group. And would thus be likely to
have a weak hydrogen bond to water.
I thought this would not be the case, even though the large electron density.
Thoughts?
kavu - 15-2-2013 at 16:05
This page should settle your argument:
http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch20reactionsnitriles.html
If you want a MO-approach then the nitrile HOMO (nucleophilic region) protrudes away from the triple bond at the nitrogen lone pair. Overlap of
electrophiles is favoured at this end. Nitrile LUMO (electrophilic region) is bulged towards the carbon and this end will react with nucleophiles.
[Edited on 16-2-2013 by kavu]
[Edited on 16-2-2013 by kavu]
GreenD - 15-2-2013 at 16:09
PRetty clear, thanks.