Structuresof 2,2′-bis(dimethylamino)biphenyl and its monohydrobromide)

Staab, Heinz A.; Krieger, Claus; Höne, Matthias

doi:10.1016/S0040-4039(00)80830-8

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Structuresof 2,2′-bis(dimethylamino)biphenyl and its monohydrobromide)

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Staab, Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Krieger, Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Höne, Matthias
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Staab, H. A., Krieger, C., & Höne, M. (1988). Structuresof 2,2′-bis(dimethylamino)biphenyl and its monohydrobromide). Tetrahedron Letters, 29(4), 5629-5632. doi:10.1016/S0040-4039(00)80830-8.

Cite as: https://hdl.handle.net/21.11116/0000-000A-577E-8

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.