Synthesis and characterization of an amidinate-stabilized cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] and a singlet delocalized biradicaloid [LSi(μ2-C2Ph2)2SiL]

Hui Xian Yeong; Hong Wei Xi; Kok Hwa Lim; Cheuk Wai So

doi:10.1002/chem.201001141

Synthesis and characterization of an amidinate-stabilized cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] and a singlet delocalized biradicaloid [LSi(μ₂-C₂Ph₂)₂SiL]

Hui Xian Yeong, Hong Wei Xi, Kok Hwa Lim, Cheuk Wai So^*

^*Corresponding author for this work

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

56 Citations (Scopus)

Abstract

The synthesis and characterization of novel cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] (2; L=PhC(NtBu)₂) and a singlet delocalized biradicaloid [LSi(μ₂-C₂Ph₂)₂SiL] (3) are described. Compound 2 was prepared by the reaction of [{PhC(NtBu) ₂}Si:]₂ (1) with one equivalent of PhC?CH in toluene. Compound 3 was synthesized by the reaction of 1 with two equivalents of PhC≡CPh in toluene. The results suggest that the reaction proceeds through an [LSi{C(Ph)=C(Ph)}SiL] intermediate, which then reacts with another molecule of PhC≡CPh to form 3. Compounds 2 and 3 have been characterized by X-ray crystallography and NMR spectroscopy. X-ray crystallography and DFT calculations of 3 show that the singlet biradicals are stabilized by the amidinate ligand and the delocalization within the "Si(μ₂-C₂Ph ₂)₂Si" six-membered ring.

Original language	English
Pages (from-to)	12956-12961
Number of pages	6
Journal	Chemistry - A European Journal
Volume	16
Issue number	43
DOIs	https://doi.org/10.1002/chem.201001141
Publication status	Published - Nov 15 2010
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Organic Chemistry

Keywords

density functional calculations
N ligands
radicals
silicon
silylene

Access to Document

10.1002/chem.201001141

Cite this

@article{3c16437be42c488e9e48e47c86091336,

title = "Synthesis and characterization of an amidinate-stabilized cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] and a singlet delocalized biradicaloid [LSi(μ2-C2Ph2)2SiL]",

abstract = "The synthesis and characterization of novel cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] (2; L=PhC(NtBu)2) and a singlet delocalized biradicaloid [LSi(μ2-C2Ph2)2SiL] (3) are described. Compound 2 was prepared by the reaction of [{PhC(NtBu) 2}Si:]2 (1) with one equivalent of PhC?CH in toluene. Compound 3 was synthesized by the reaction of 1 with two equivalents of PhC≡CPh in toluene. The results suggest that the reaction proceeds through an [LSi{C(Ph)=C(Ph)}SiL] intermediate, which then reacts with another molecule of PhC≡CPh to form 3. Compounds 2 and 3 have been characterized by X-ray crystallography and NMR spectroscopy. X-ray crystallography and DFT calculations of 3 show that the singlet biradicals are stabilized by the amidinate ligand and the delocalization within the {"}Si(μ2-C2Ph 2)2Si{"} six-membered ring.",

keywords = "density functional calculations, N ligands, radicals, silicon, silylene",

author = "Yeong, {Hui Xian} and Xi, {Hong Wei} and Lim, {Kok Hwa} and So, {Cheuk Wai}",

year = "2010",

month = nov,

day = "15",

doi = "10.1002/chem.201001141",

language = "English",

volume = "16",

pages = "12956--12961",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "43",

}

Synthesis and characterization of an amidinate-stabilized cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] and a singlet delocalized biradicaloid [LSi(μ₂-C₂Ph₂)₂SiL]. / Yeong, Hui Xian; Xi, Hong Wei; Lim, Kok Hwa et al.
In: Chemistry - A European Journal, Vol. 16, No. 43, 15.11.2010, p. 12956-12961.

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

TY - JOUR

T1 - Synthesis and characterization of an amidinate-stabilized cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] and a singlet delocalized biradicaloid [LSi(μ2-C2Ph2)2SiL]

AU - Yeong, Hui Xian

AU - Xi, Hong Wei

AU - Lim, Kok Hwa

AU - So, Cheuk Wai

PY - 2010/11/15

Y1 - 2010/11/15

N2 - The synthesis and characterization of novel cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] (2; L=PhC(NtBu)2) and a singlet delocalized biradicaloid [LSi(μ2-C2Ph2)2SiL] (3) are described. Compound 2 was prepared by the reaction of [{PhC(NtBu) 2}Si:]2 (1) with one equivalent of PhC?CH in toluene. Compound 3 was synthesized by the reaction of 1 with two equivalents of PhC≡CPh in toluene. The results suggest that the reaction proceeds through an [LSi{C(Ph)=C(Ph)}SiL] intermediate, which then reacts with another molecule of PhC≡CPh to form 3. Compounds 2 and 3 have been characterized by X-ray crystallography and NMR spectroscopy. X-ray crystallography and DFT calculations of 3 show that the singlet biradicals are stabilized by the amidinate ligand and the delocalization within the "Si(μ2-C2Ph 2)2Si" six-membered ring.

AB - The synthesis and characterization of novel cis-1,2-disilylenylethene [cis-LSi{C(Ph)=C(H)}SiL] (2; L=PhC(NtBu)2) and a singlet delocalized biradicaloid [LSi(μ2-C2Ph2)2SiL] (3) are described. Compound 2 was prepared by the reaction of [{PhC(NtBu) 2}Si:]2 (1) with one equivalent of PhC?CH in toluene. Compound 3 was synthesized by the reaction of 1 with two equivalents of PhC≡CPh in toluene. The results suggest that the reaction proceeds through an [LSi{C(Ph)=C(Ph)}SiL] intermediate, which then reacts with another molecule of PhC≡CPh to form 3. Compounds 2 and 3 have been characterized by X-ray crystallography and NMR spectroscopy. X-ray crystallography and DFT calculations of 3 show that the singlet biradicals are stabilized by the amidinate ligand and the delocalization within the "Si(μ2-C2Ph 2)2Si" six-membered ring.

KW - density functional calculations

KW - N ligands

KW - radicals

KW - silicon

KW - silylene

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