N-heterocyclic germylenes : structural characterisation of some heavy analogues of the ubiquitous N-heterocyclic carbenes

Tools

Dodds, Christopher A. and Kennedy, Alan R. and Spicer, Mark D. (2019) N-heterocyclic germylenes : structural characterisation of some heavy analogues of the ubiquitous N-heterocyclic carbenes. Heteroatom Chemistry, 2019. 9178371. ISSN 1042-7163 (https://doi.org/10.1155/2019/9178371)

[thumbnail of Dodds-etal-HC-2018-structural-characterisation-of-some-heavy-analogues-of-the-ubiquitous-N-heterocyclic-carbenes] Text. Filename: Dodds_etal_HC_2018_structural_characterisation_of_some_heavy_analogues_of_the_ubiquitous_N_heterocyclic_carbenes.pdf
Final Published Version
License: Creative Commons Attribution 4.0 logo
Download (2MB)

Abstract

The X-ray crystal structures of three N-heterocyclic germylenes (NHGes) have been elucidated including the previously unknown 1,3-bis(2,6-dimethylphenyl)diazagermol-2-ylidene (1). In addition, the X-ray crystal structures of the previously synthesised 1,3-bis(2,4,6-trimethylphenyl)diazagermol-2-ylidene (2) and 1,3-bis(2,6-diisopropylphenyl)diazagermol-2-ylidene (3) are also reported. The discrete molecular structures of compounds 1 to 3 are comparable, with Ge-N bond lengths in the range 1.835-1.875 Å, while the N-Ge-N bond angles range between 83.6 and 85.2°. Compound 2 was compared to the analogous N-heterocyclic carbene species, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes). The major geometrical difference observed, as expected, was the bond angle around the divalent group 14 atom. The N-Ge-N bond angle was 83.6° for compound 2 versus the N-C-N bond angle of 101.4° for IMes. The Sn equivalent of (1), 1,3-bis(2,6-dimethylphenyl)diazastannol-2-ylidene (4), has also been synthesised and its crystal structure is reported here. In order to test their suitability as ligands, compounds 1 to 3 were reacted with a wide range of transition metal complexes. No NHGes containing metal complexes were observed. In all cases the NHGe either degraded or gave no reaction.

ORCID iDs

Dodds, Christopher A. ORCID logoORCID: https://orcid.org/0000-0002-4590-0307, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Spicer, Mark D. ORCID logoORCID: https://orcid.org/0000-0002-6000-5677;
  • Item type:Article
    ID code:66817
    Dates:
    Date
    Event
    23 January 2019
    Published
    11 December 2018
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:05 Feb 2019 11:00
    Last modified:11 Nov 2024 12:13
    URI:https://strathprints.strath.ac.uk/id/eprint/66817
CORE (COnnecting REpositories)