The structure of 1,6-diazabicyclo[4.4.4]tetradecane and of its inside protonated ion

Abstract
1,6-Diazabicyclo[4.4.4]tetradecane (1) and its inside-protonated ion (4) are essentially isostructural with effective D3 symmetry; the N,N′ distance contracts by 0.28 Å on protonated, giving the shortest known N–H:N hydrogen bond (2.53 Å).

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