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

Nelsen, Stephen F. and Konradsson, Asgeir E. and Ismagilov, Rustem F. and Guzei, Ilia A. (2005) Crystallographic characterization of the geometry changes upon electron loss from 2-tert-butyl-3-aryl-2,3-diazabicyclo 2.2.2 octanes. Crystal Growth and Design, 5 (6). pp. 2344-2347. ISSN 1528-7483. doi:10.1021/cg050154w.

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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-(1-naphthyl)-2,3-diazabicyclo[2.2.2]octane radical cation hexafluoroantiminate (Hy^1NA+SbF_6-); 2-tert-butyl-3-(2-naphthyl)-2,3-diazabicyclo-[2.2.2]octane radical cation hexafluoroantiminate (Hy^2NA+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+)(Ph_4B^-)_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+)(SbF_6^-)_2·CH_3CN) 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 (θ(0)) in the range 122−130°, are compared with those for tetraalkylhydrazines that have θ(0) values near 180, 90, and 0°.

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Ismagilov, Rustem F.0000-0002-3680-4399
Additional Information:Copyright © 2005 American Chemical Society. Published In Issue: November 02, 2005. Received April 14, 2005. Revised Manuscript Received May 12, 2005. We thank the National Science Foundation for partial financial support under CHE-9988727 and CHE-0240197 (S.F.N.) and CHE-9310428 for the purchase of X-ray instrument and computers. We thank Douglas R. Powell and Randy K. Hayashi for the determination of X-ray structures. Note Added after ASAP Publication: An earlier version of this paper posted ASAP on the web on July 14, 2005, contained two errors in the compound names on lines 15 and 16 of the abstract. The names have been corrected in this new version posted September 30, 2005. Supporting Information Available: Summary of the data used to give the ranges in Table 5. Crystal structural data for HyDU^+NO_3^-, Hy^1NA^+SbF_6^-, Hy^2NA^+SbF_6^-, Hy_2^(15)NA^(2+)(Ph_4B^-)_2, and Hy_2^(27)NA^(2+)(SbF_6^-)_2·CH_3CN. This material is available free of charge via the Internet at
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Subject Keywords:pair dihedral angles; photoelectron-spectra; intervalence compounds; radical cations; transfer rates; hydrazines; state
Issue or Number:6
Record Number:CaltechAUTHORS:20130821-160727982
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:40848
Deposited By: Whitney Barlow
Deposited On:28 Aug 2013 18:28
Last Modified:10 Nov 2021 00:09

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