Posts Tagged ‘Phenyl group’

Ammonium tetraphenylborate and the mystery of its π-facial hydrogen bonding.

Friday, March 10th, 2017

A few years back, I did a post about the Pirkle reagent[cite]10.1039/c39910000765[/cite] and the unusual π-facial hydrogen bonding structure[cite]10.1039/P29940000703[/cite] it exhibits. For the Pirkle reagent, this bonding manifests as a close contact between the acidic OH hydrogen and the edge of a phenyl ring; the hydrogen bond is off-centre from the middle of the aryl ring. Here I update the topic, with a new search of the CSD (Cambridge structure database), but this time looking at the positional preference of that bond and whether it is on or off-centre. 

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