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Article

Influence of Fluorine Substituents on the Electronic Properties of Selenium-N-Heterocyclic Carbene Compounds

1
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310 UTM, Johor, Malaysia
2
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang 43400 UPM, Selangor, Malaysia
*
Authors to whom correspondence should be addressed.
Academic Editor: Francesca Marini
Received: 4 October 2020 / Revised: 21 October 2020 / Accepted: 22 October 2020 / Published: 6 November 2020
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
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. View Full-Text
Keywords: N-heterocyclic carbene; selenium; fluorine; NMR spectroscopy N-heterocyclic carbene; selenium; fluorine; NMR spectroscopy
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MDPI and ACS Style

Jamil, M.S.S.; Endot, N.A. Influence of Fluorine Substituents on the Electronic Properties of Selenium-N-Heterocyclic Carbene Compounds. Molecules 2020, 25, 5161. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25215161

AMA Style

Jamil MSS, Endot NA. Influence of Fluorine Substituents on the Electronic Properties of Selenium-N-Heterocyclic Carbene Compounds. Molecules. 2020; 25(21):5161. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25215161

Chicago/Turabian Style

Jamil, Mohamad S.S., and Nor A. Endot. 2020. "Influence of Fluorine Substituents on the Electronic Properties of Selenium-N-Heterocyclic Carbene Compounds" Molecules 25, no. 21: 5161. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25215161

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