Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds
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 chan...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Multidisciplinary Digital Publishing Institute
2020
|
| Online Access: | http://psasir.upm.edu.my/id/eprint/89367/ http://psasir.upm.edu.my/id/eprint/89367/1/FLUO.pdf |
| _version_ | 1848860837376163840 |
|---|---|
| author | Jamil, Mohamad Shazwan Shah Endot, Nor Azam |
| author_facet | Jamil, Mohamad Shazwan Shah Endot, Nor Azam |
| author_sort | Jamil, Mohamad Shazwan Shah |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-15T12:51:35Z |
| format | Article |
| id | upm-89367 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T12:51:35Z |
| publishDate | 2020 |
| publisher | Multidisciplinary Digital Publishing Institute |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-893672021-08-19T00:59:10Z http://psasir.upm.edu.my/id/eprint/89367/ Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds Jamil, Mohamad Shazwan Shah Endot, Nor Azam 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. Multidisciplinary Digital Publishing Institute 2020 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/89367/1/FLUO.pdf 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 https://www.mdpi.com/1420-3049/25/21/5161 10.3390/molecules25215161 |
| spellingShingle | Jamil, Mohamad Shazwan Shah Endot, Nor Azam Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds |
| title | Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds |
| title_full | Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds |
| title_fullStr | Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds |
| title_full_unstemmed | Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds |
| title_short | Influence of fluorine substituents on the electronic properties of selenium-N-heterocyclic carbene compounds |
| title_sort | influence of fluorine substituents on the electronic properties of selenium-n-heterocyclic carbene compounds |
| url | http://psasir.upm.edu.my/id/eprint/89367/ http://psasir.upm.edu.my/id/eprint/89367/ http://psasir.upm.edu.my/id/eprint/89367/ http://psasir.upm.edu.my/id/eprint/89367/1/FLUO.pdf |