I have previously commented on the Bürgi–Dunitz angle, this being the preferred approach trajectory of a nucleophile towards the electrophilic carbon of a carbonyl group. Some special types of nucleophile such as hydrazines (R2N-NR2) are supposed to have enhanced reactivity[cite]10.1016/S0040-4020(01)93101-1[/cite] due to what might be described as buttressing of adjacent lone pairs. Here I focus in on how this might manifest by performing searches of the Cambridge structural database for intermolecular (non-bonded) interactions between X-Y nucleophiles (X,Y= N,O,S) and carbonyl compounds OC(NM)2.
Posts Tagged ‘Superbase’
What is the approach trajectory of enhanced (super?) nucleophiles towards a carbonyl group?
Wednesday, May 11th, 2016Tags:Bases, Bürgi–Dunitz angle, Carbonyl, Electrophile, Ester, Flippin–Lodge angle, Functional groups, hydrazine, non-metal attachments, Nucleophile, Physical organic chemistry, search query, Superbase
Posted in Chemical IT, crystal_structure_mining | 1 Comment »