2,6-Diaziadamantane: A single-crystal x-ray diffraction study and theoretical calculations
- Author(s)
- Michael Bobek, Daniel Krois, Thomas H. Brehmer, Gerald Giester, Kenneth B. Wiberg, Udo H. Brinker
- Abstract
The first single-crystal X-ray diffraction study of 2,6-diaziadamantane (2), a compound containing two diazirine functionalities, and B3LYP/6-311+G* and MP2/6-311+G* calculations relating to the interaction between carbon-nitrogen and nitrogen-nitrogen covalent bonds and electron density within the diazirine rings have been performed. In addition, the protonation of 2-aziadamantane (1) has been investigated. The single-crystal X-ray diffraction study of 2, including UV/vis titrations of 1, corroborate the theoretical conclusion that the low basicity can be attributed to a rehybridization of the nitrogen lone pairs. Moreover, the strain in diazirine is unusually small.
- Organisation(s)
- Department of Organic Chemistry, Department of Mineralogy and Crystallography
- External organisation(s)
- Yale University, University of Vienna
- Journal
- The Journal of Organic Chemistry
- Volume
- 68
- Pages
- 2129-2134
- No. of pages
- 6
- ISSN
- 0022-3263
- DOI
- https://doi.org/10.1021/jo020536y
- Publication date
- 2003
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 1051 Geology, Mineralogy
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/4a92296a-809f-451a-9a62-1447bc6c1417