Isolable dicarbon stabilized by a single phosphine ligand

Tsz Fai Leung; Dandan Jiang; Ming Chun Wu; Dengmengfei Xiao; Wei Min Ching; Glenn P.A. Yap; Tao Yang; Lili Zhao; Tiow Gan Ong; Gernot Frenking

doi:10.1038/s41557-020-00579-w

Isolable dicarbon stabilized by a single phosphine ligand

Tsz Fai Leung, Dandan Jiang, Ming Chun Wu, Dengmengfei Xiao, Wei Min Ching, Glenn P.A. Yap, Tao Yang, Lili Zhao, Tiow Gan Ong, Gernot Frenking

School of Chemistry and Moleculai Engineering

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

20 Scopus citations

Abstract

In contrast to naturally occurring F₂, O₂ and N₂, diatomic C₂ is an intriguing species that has only been observed indirectly in the gas phase, and because of its high reactivity has eluded isolation in the condensed phase. It has previously been stabilized in L→C₂←L compounds but the bonding situation of the central C₂ in this motif differs remarkably from that of free C₂. Here we have prepared and structurally characterized diatomic C₂ as a monoligated complex L→C₂ using a bulky phosphine ligand bearing two imidazolidin-2-iminato groups (L is (NHC^R=N)₂(CH₃)P, where NHC^R is an N-heterocyclic carbene). The compound is stable in solution at ambient temperature and has also been isolated in the solid state. Reactivity studies, in combination with quantum chemical analysis, suggest that the two carbon atoms of the L→C₂ complex both have carbene character. The complex underwent intermolecular C–H bond activation upon thermolysis and exhibited hydroalkoxylation-like reactivity with methanol. [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	89-93
Number of pages	5
Journal	Nature Chemistry
Volume	13
Issue number	1
DOIs	https://doi.org/10.1038/s41557-020-00579-w
State	Published - Jan 2021

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title = "Isolable dicarbon stabilized by a single phosphine ligand",

abstract = "In contrast to naturally occurring F2, O2 and N2, diatomic C2 is an intriguing species that has only been observed indirectly in the gas phase, and because of its high reactivity has eluded isolation in the condensed phase. It has previously been stabilized in L→C2←L compounds but the bonding situation of the central C2 in this motif differs remarkably from that of free C2. Here we have prepared and structurally characterized diatomic C2 as a monoligated complex L→C2 using a bulky phosphine ligand bearing two imidazolidin-2-iminato groups (L is (NHCR=N)2(CH3)P, where NHCR is an N-heterocyclic carbene). The compound is stable in solution at ambient temperature and has also been isolated in the solid state. Reactivity studies, in combination with quantum chemical analysis, suggest that the two carbon atoms of the L→C2 complex both have carbene character. The complex underwent intermolecular C–H bond activation upon thermolysis and exhibited hydroalkoxylation-like reactivity with methanol. [Figure not available: see fulltext.]",

author = "Leung, {Tsz Fai} and Dandan Jiang and Wu, {Ming Chun} and Dengmengfei Xiao and Ching, {Wei Min} and Yap, {Glenn P.A.} and Tao Yang and Lili Zhao and Ong, {Tiow Gan} and Gernot Frenking",

note = "Publisher Copyright: {\textcopyright} 2020, The Author(s), under exclusive licence to Springer Nature Limited.",

year = "2021",

month = jan,

doi = "10.1038/s41557-020-00579-w",

language = "英语",

volume = "13",

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TY - JOUR

T1 - Isolable dicarbon stabilized by a single phosphine ligand

AU - Leung, Tsz Fai

AU - Jiang, Dandan

AU - Wu, Ming Chun

AU - Xiao, Dengmengfei

AU - Ching, Wei Min

AU - Yap, Glenn P.A.

AU - Yang, Tao

AU - Zhao, Lili

AU - Ong, Tiow Gan

AU - Frenking, Gernot

PY - 2021/1

Y1 - 2021/1

N2 - In contrast to naturally occurring F2, O2 and N2, diatomic C2 is an intriguing species that has only been observed indirectly in the gas phase, and because of its high reactivity has eluded isolation in the condensed phase. It has previously been stabilized in L→C2←L compounds but the bonding situation of the central C2 in this motif differs remarkably from that of free C2. Here we have prepared and structurally characterized diatomic C2 as a monoligated complex L→C2 using a bulky phosphine ligand bearing two imidazolidin-2-iminato groups (L is (NHCR=N)2(CH3)P, where NHCR is an N-heterocyclic carbene). The compound is stable in solution at ambient temperature and has also been isolated in the solid state. Reactivity studies, in combination with quantum chemical analysis, suggest that the two carbon atoms of the L→C2 complex both have carbene character. The complex underwent intermolecular C–H bond activation upon thermolysis and exhibited hydroalkoxylation-like reactivity with methanol. [Figure not available: see fulltext.]

AB - In contrast to naturally occurring F2, O2 and N2, diatomic C2 is an intriguing species that has only been observed indirectly in the gas phase, and because of its high reactivity has eluded isolation in the condensed phase. It has previously been stabilized in L→C2←L compounds but the bonding situation of the central C2 in this motif differs remarkably from that of free C2. Here we have prepared and structurally characterized diatomic C2 as a monoligated complex L→C2 using a bulky phosphine ligand bearing two imidazolidin-2-iminato groups (L is (NHCR=N)2(CH3)P, where NHCR is an N-heterocyclic carbene). The compound is stable in solution at ambient temperature and has also been isolated in the solid state. Reactivity studies, in combination with quantum chemical analysis, suggest that the two carbon atoms of the L→C2 complex both have carbene character. The complex underwent intermolecular C–H bond activation upon thermolysis and exhibited hydroalkoxylation-like reactivity with methanol. [Figure not available: see fulltext.]

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DO - 10.1038/s41557-020-00579-w

M3 - 文章

C2 - 33257886

AN - SCOPUS:85096919377

SN - 1755-4330

VL - 13

SP - 89

EP - 93

JO - Nature Chemistry

JF - Nature Chemistry

IS - 1

ER -

Isolable dicarbon stabilized by a single phosphine ligand

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