2,6-Diaziadamantane: A single-crystal x-ray diffraction study and theoretical calculations

Autor(en)

Michael Bobek, Daniel Krois, Thomas H. Brehmer, Gerald Giester, Kenneth B. Wiberg, Udo H. Brinker

Abstrakt

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(en)

Institut für Organische Chemie, Institut für Mineralogie und Kristallographie

Externe Organisation(en)

Yale University, Universität Wien

Journal

The Journal of Organic Chemistry

Band

68

Seiten

2129-2134

Anzahl der Seiten

6

ISSN

0022-3263

DOI

https://doi.org/10.1021/jo020536y

Publikationsdatum

2003

Peer-reviewed

Ja

ÖFOS 2012

1051 Geologie, Mineralogie

Link zum Portal

https://ucrisportal.univie.ac.at/de/publications/4a92296a-809f-451a-9a62-1447bc6c1417