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In silico olefin metathesis with Ru-based catalysts containing N-heterocyclic carbenes bearing C-60 fullerenes

Juan Pablo Martinez, Sai Vikrama Chaitanya Vummaleti, Laura Falivene, Steven Nolan UGent, Luigi Cavallo, Miquel Sola and Albert Poater (2016) CHEMISTRY-A EUROPEAN JOURNAL. 22(19). p.6617-6623
abstract
Density functional theory calculations have been used to explore the potential of Ru-based complexes with 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (SIMes) ligand backbone (A) being modified in silico by the insertion of a C-60 molecule (B and C), as olefin metathesis catalysts. To this end, we investigated the olefin metathesis reaction catalyzed by complexes A, B, and C using ethylene as the substrate, focusing mainly on the thermodynamic stability of all possible reaction intermediates. Our results suggest that complex B bearing an electron-withdrawing N-heterocyclic carbene improves the performance of unannulated complex A. The efficiency of complex B is only surpassed by complex A when the backbone of the N-heterocyclic carbene of complex A is substituted by two amino groups. The particular performance of complexes B and C has to be attributed to electronic factors, that is, the electronic-donating capacity of modified SIMes ligand rather than steric effects, because the latter are predicted to be almost identical for complexes B and C when compared to those of A. Overall, this study indicates that such Ru-based complexes B and C might have the potential to be effective olefin metathesis catalysts.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
density functional calculations, fullerene, metallacycles, metathesis, ruthenium, DENSITY-FUNCTIONAL THEORY, RING-CLOSING METATHESIS, STRUCTURE-PROPERTY RELATIONSHIPS, RUTHENIUM COMPLEXES RELEVANT, TRANSITION-METAL COMPOUNDS, MOLECULAR-ORBITAL THEORY, ACTIVATION STRAIN MODEL, GRUBBS-TYPE CATALYST, ALKENE METATHESIS, NONCOVALENT INTERACTIONS
journal title
CHEMISTRY-A EUROPEAN JOURNAL
Chem.-Eur. J.
volume
22
issue
19
pages
6617 - 6623
Web of Science type
Article
Web of Science id
000374694500028
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
5.317 (2016)
JCR rank
29/166 (2016)
JCR quartile
1 (2016)
ISSN
0947-6539
DOI
10.1002/chem.201600383
language
English
UGent publication?
yes
classification
A1
id
8168157
handle
http://hdl.handle.net/1854/LU-8168157
date created
2016-11-24 15:50:09
date last changed
2018-01-29 12:12:30
@article{8168157,
  abstract     = {Density functional theory calculations have been used to explore the potential of Ru-based complexes with 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (SIMes) ligand backbone (A) being modified in silico by the insertion of a C-60 molecule (B and C), as olefin metathesis catalysts. To this end, we investigated the olefin metathesis reaction catalyzed by complexes A, B, and C using ethylene as the substrate, focusing mainly on the thermodynamic stability of all possible reaction intermediates. Our results suggest that complex B bearing an electron-withdrawing N-heterocyclic carbene improves the performance of unannulated complex A. The efficiency of complex B is only surpassed by complex A when the backbone of the N-heterocyclic carbene of complex A is substituted by two amino groups. The particular performance of complexes B and C has to be attributed to electronic factors, that is, the electronic-donating capacity of modified SIMes ligand rather than steric effects, because the latter are predicted to be almost identical for complexes B and C when compared to those of A. Overall, this study indicates that such Ru-based complexes B and C might have the potential to be effective olefin metathesis catalysts.},
  author       = {Pablo Martinez, Juan and Vummaleti, Sai Vikrama Chaitanya and Falivene, Laura and Nolan, Steven and Cavallo, Luigi and Sola, Miquel and Poater, Albert},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {density functional calculations,fullerene,metallacycles,metathesis,ruthenium,DENSITY-FUNCTIONAL THEORY,RING-CLOSING METATHESIS,STRUCTURE-PROPERTY RELATIONSHIPS,RUTHENIUM COMPLEXES RELEVANT,TRANSITION-METAL COMPOUNDS,MOLECULAR-ORBITAL THEORY,ACTIVATION STRAIN MODEL,GRUBBS-TYPE CATALYST,ALKENE METATHESIS,NONCOVALENT INTERACTIONS},
  language     = {eng},
  number       = {19},
  pages        = {6617--6623},
  title        = {In silico olefin metathesis with Ru-based catalysts containing N-heterocyclic carbenes bearing C-60 fullerenes},
  url          = {http://dx.doi.org/10.1002/chem.201600383},
  volume       = {22},
  year         = {2016},
}

Chicago
Pablo Martinez, Juan, Sai Vikrama Chaitanya Vummaleti, Laura Falivene, Steven Nolan, Luigi Cavallo, Miquel Sola, and Albert Poater. 2016. “In Silico Olefin Metathesis with Ru-based Catalysts Containing N-heterocyclic Carbenes Bearing C-60 Fullerenes.” Chemistry-a European Journal 22 (19): 6617–6623.
APA
Pablo Martinez, J., Vummaleti, S. V. C., Falivene, L., Nolan, S., Cavallo, L., Sola, M., & Poater, A. (2016). In silico olefin metathesis with Ru-based catalysts containing N-heterocyclic carbenes bearing C-60 fullerenes. CHEMISTRY-A EUROPEAN JOURNAL, 22(19), 6617–6623.
Vancouver
1.
Pablo Martinez J, Vummaleti SVC, Falivene L, Nolan S, Cavallo L, Sola M, et al. In silico olefin metathesis with Ru-based catalysts containing N-heterocyclic carbenes bearing C-60 fullerenes. CHEMISTRY-A EUROPEAN JOURNAL. 2016;22(19):6617–23.
MLA
Pablo Martinez, Juan, Sai Vikrama Chaitanya Vummaleti, Laura Falivene, et al. “In Silico Olefin Metathesis with Ru-based Catalysts Containing N-heterocyclic Carbenes Bearing C-60 Fullerenes.” CHEMISTRY-A EUROPEAN JOURNAL 22.19 (2016): 6617–6623. Print.