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Abstract:
In the context of ‘proton sponge’ systems, for the conformationally flexible biphenyl 1 the X-ray structure analysis as well as the basicity have been determined. 1 forms monoprotonated salts of which the structure of the hydrobromide 1a·BrX was solved. It contains a ‘proton sponge’-like N⋯H⋯N hydrogen bridge to which the 1000-fold increase of the basicity constant as compared to N,N-dimethylaniline is attributed.
Protonation of 1, in spite of the conformational flexibility, leads to a strong N⋯H⋯N hydrogen bond like in ‘proton sponges’ as structure determination of 1 and 1a reveals.
