Cubyl anion

Cubyl anion has been prepared by reacting (trimethylsilyl)cubane with fluoride ion in a Fourier transform mass spectrometer and its reactions with acids such as H2O, Me2NH, EtNH2, MeNH2, and NH3 have been monitored. The results suggest that cubane is thermodynamically more acidic than cyclopropane. The electron affinity of the cubyl radical and the C—H BDE for cubane have also been estimated.126... 

The acidity of the unadivated cubyl-H is comparable to NH3 (pKa 38). Cubyl H-atoms are at least 105-106 times more acidic than vinyl and phenyl hydrogens (K. A. Lukin, J. Li, P. E. Eaton, N. Kanomata, J. Hain, E. Pun-zalan, R. Gilardi, Synthesis and chemistry of 1,35,7-tetranitrocubane induding measurement of its acidity, formation of o-nitro anions, and the first preparations of pentanitrocubane and hexanitrocubane , J. Am Chem. Soc, 1997,119, 9591-9602 and the references cited therein). 

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