Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)

Alba Collado; János Balogh; Sébastien Meiries; Alexandra M. Z. Slawin; Laura Falivene; Luigi Cavallo; Steven P. Nolan

doi:10.1021/om400168b

Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)

Alba Collado, János Balogh, Sébastien Meiries, Alexandra M. Z. Slawin, Laura Falivene, Luigi Cavallo, Steven P. Nolan

Research output: Contribution to journal › Article › peer-review

55 Scopus citations

Abstract

The free N-heterocyclic carbene IPent (1; IPent = 1,3-bis(2,6-bis(1- ethylpropyl)phenyl)imidazol-2-ylidene) was prepared from the corresponding imidazolium chloride salt (2). The steric and electronic parameters of 1 were determined by synthesis of the gold(I) chloride complex [Au(IPent)Cl] (3) and the nickel-carbonyl complex [Ni(IPent)(CO)3] (4), respectively. 3 and 4 were fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction studies on single crystals. © 2013 American Chemical Society.

Original language	English (US)
Pages (from-to)	3249-3252
Number of pages	4
Journal	Organometallics
Volume	32
Issue number	11
DOIs	https://doi.org/10.1021/om400168b
State	Published - May 28 2013

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The ERC (Advanced Investigator Award-FUNCAT), Umicore, Syngenta and the EPSRC are thanked for support of this work. We thank the EPSRC National Mass Spectrometry Service Center in Swansea for mass analyses. S.P.N. is a Royal Society Wolfson Research Merit Award holder.

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1021/om400168b

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@article{dff01af077db43fa9e5c78e25a62e8f0,

title = "Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)",

abstract = "The free N-heterocyclic carbene IPent (1; IPent = 1,3-bis(2,6-bis(1- ethylpropyl)phenyl)imidazol-2-ylidene) was prepared from the corresponding imidazolium chloride salt (2). The steric and electronic parameters of 1 were determined by synthesis of the gold(I) chloride complex [Au(IPent)Cl] (3) and the nickel-carbonyl complex [Ni(IPent)(CO)3] (4), respectively. 3 and 4 were fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction studies on single crystals. {\textcopyright} 2013 American Chemical Society.",

author = "Alba Collado and J{\'a}nos Balogh and S{\'e}bastien Meiries and Slawin, {Alexandra M. Z.} and Laura Falivene and Luigi Cavallo and Nolan, {Steven P.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The ERC (Advanced Investigator Award-FUNCAT), Umicore, Syngenta and the EPSRC are thanked for support of this work. We thank the EPSRC National Mass Spectrometry Service Center in Swansea for mass analyses. S.P.N. is a Royal Society Wolfson Research Merit Award holder.",

year = "2013",

month = may,

day = "28",

doi = "10.1021/om400168b",

language = "English (US)",

volume = "32",

pages = "3249--3252",

journal = "Organometallics",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)

AU - Collado, Alba

AU - Balogh, János

AU - Meiries, Sébastien

AU - Slawin, Alexandra M. Z.

AU - Falivene, Laura

AU - Cavallo, Luigi

AU - Nolan, Steven P.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The ERC (Advanced Investigator Award-FUNCAT), Umicore, Syngenta and the EPSRC are thanked for support of this work. We thank the EPSRC National Mass Spectrometry Service Center in Swansea for mass analyses. S.P.N. is a Royal Society Wolfson Research Merit Award holder.

PY - 2013/5/28

Y1 - 2013/5/28

N2 - The free N-heterocyclic carbene IPent (1; IPent = 1,3-bis(2,6-bis(1- ethylpropyl)phenyl)imidazol-2-ylidene) was prepared from the corresponding imidazolium chloride salt (2). The steric and electronic parameters of 1 were determined by synthesis of the gold(I) chloride complex [Au(IPent)Cl] (3) and the nickel-carbonyl complex [Ni(IPent)(CO)3] (4), respectively. 3 and 4 were fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction studies on single crystals. © 2013 American Chemical Society.

AB - The free N-heterocyclic carbene IPent (1; IPent = 1,3-bis(2,6-bis(1- ethylpropyl)phenyl)imidazol-2-ylidene) was prepared from the corresponding imidazolium chloride salt (2). The steric and electronic parameters of 1 were determined by synthesis of the gold(I) chloride complex [Au(IPent)Cl] (3) and the nickel-carbonyl complex [Ni(IPent)(CO)3] (4), respectively. 3 and 4 were fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction studies on single crystals. © 2013 American Chemical Society.

UR - http://hdl.handle.net/10754/562808

UR - https://pubs.acs.org/doi/10.1021/om400168b

UR - http://www.scopus.com/inward/record.url?scp=84878838309&partnerID=8YFLogxK

U2 - 10.1021/om400168b

DO - 10.1021/om400168b

M3 - Article

SN - 0276-7333

VL - 32

SP - 3249

EP - 3252

JO - Organometallics

JF - Organometallics

IS - 11

ER -

Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)

Abstract

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CCDC 926491: Experimental Crystal Structure Determination : Chloro-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)imidazol-2-ylidene)-gold

CCDC 926492: Experimental Crystal Structure Determination : Tricarbonyl-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)imidazol-2-ylidene)-nickel

Cite this

Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 926491: Experimental Crystal Structure Determination : Chloro-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)imidazol-2-ylidene)-gold

CCDC 926492: Experimental Crystal Structure Determination : Tricarbonyl-(1,3-bis(2,6-bis(pentan-3-yl)phenyl)imidazol-2-ylidene)-nickel

Cite this