2,6-Diaziadamantane:  A Single-Crystal X-ray Diffraction Study and Theoretical Calculations

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...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2003-03, Vol.68 (6), p.2129-2134
Main Authors: Bobek, Michael M, Krois, Daniel, Brehmer, Thomas H, Giester, Gerald, Wiberg, Kenneth B, Brinker, Udo H
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020536y