title: 2,6-Diaziadamantane: a single-crystal X-ray diffraction study and theoretical calculations.
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.
authors.affiliation: Institut für Organische Chemie, Universität Wien, Austria.
authors.forename: Michael M
authors.initials: MM
authors.lastname: Bobek
authors.forename: Daniel
authors.initials: D
authors.lastname: Krois
authors.forename: Thomas H
authors.initials: TH
authors.lastname: Brehmer
authors.forename: Gerald
authors.initials: G
authors.lastname: Giester
authors.forename: Kenneth B
authors.initials: KB
authors.lastname: Wiberg
authors.forename: Udo H
authors.initials: UH
authors.lastname: Brinker