Crystallographic characterization of the geometry changes upon electron loss from 2-tert-butyl-3-aryl-2,3-diazabicyclo[2.2.2]octanes

  • Nelsen S
  • Konradsson A
  • Ismagilov R
 et al. 
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Crystal structures of 2-tert-butyl-3-(2,3,5,6-tetramethylphenyl)-2,3-diazabicyclo [2.2.2] -octane radical cation nitrate (HyDU(+)NO(3)(-)) [Hy = (2-tert-butyl-2,3-diazabicyclo[2.2.2]oct-3-yl]; 2-tert-butyl-3-(l-naphthyl)-2,3-diazabicyclo [2.2.2] octane radical cation hexafluoroantiminate (Hy(1)NA(+)SbF(6)(-)); 2-tert-butyl-3-(2-naphthyl)-2,3diazabicyclo- [2.2.2] octane radical cation hexafluoroantiminate (Hy(2)NA(+)SbF(6)(-)); 1,5-bis(2-tert-butyl-2,3-diazabicyclo[2.2.2]oct-3-yl)naphthalene dication bis(tetraphenylborate) (Hy(2)(15)NA(2+)(Ph4B-)(2)); and 2,7-bis(2-tert-butyl-2,3-diazabicyclo [2.2.2] oct-3-yl)naphthalene dication bis(hexafluoroantiminate) (Hy(2)(27)NA(2+)(SbF6-)(CH3CN)-C-2.) are reported, and the geometries about the oxidized Hy units compared with literature data for neutral Hy-substituted analogues and the geometry changes upon electron loss for these compounds, which have a lone pair, lone pair twist angle in the neutral form (theta(0)) in the range 122-130 degrees, are compared with those for tetraalkylhydrazines that have theta(0) values near 180, 90, and 0 degrees.

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