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Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds


Jamil, Mohamad Shazwan Shah and Endot, Nor Azam (2020) Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds. Molecules, 25 (21). pp. 1-10. ISSN 1420-3049


N-heterocyclic carbenes (NHCs) are common ancillary ligands in organometallic compounds that are used to alter the electronic and steric properties of a metal centre. To date, various NHCs have been synthesised with different electronic properties, which can be done by modifying the backbone or changing the nitrogen substituents group. This study describes a systematic modification of NHCs by the inclusion of fluorine substituents and examines the use of selenium-NHC compounds to measure the π-accepting ability of these fluorinated NHC ligands. Evaluation of the 77Se NMR chemical shifts of the selenium adducts reveals that fluorinated NHCs have higher chemical shifts than the non-fluorinated counterparts, IMes and IPh. Higher 77Se NMR chemical shifts values indicate a stronger π-accepting ability of the NHC ligands. The findings of this study suggest that the presence of fluorine atoms has increased the π-accepting ability of the corresponding NHC ligands. This work supports the advantage of the 77Se NMR chemical shifts of selenium-NHC compounds for assessing the influence of fluorine substituents on NHC ligands.

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Additional Metadata

Item Type: Article
Divisions: Faculty of Science
DOI Number: https://doi.org/10.3390/molecules25215161
Publisher: Multidisciplinary Digital Publishing Institute
Keywords: N-heterocyclic carbene; Selenium; Fluorine; NMR spectroscopy
Depositing User: Ms. Nuraida Ibrahim
Date Deposited: 19 Aug 2021 00:59
Last Modified: 19 Aug 2021 00:59
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.3390/molecules25215161
URI: http://psasir.upm.edu.my/id/eprint/89367
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