Taming copper(I) cyanate and selenocyanate with N-heterocyclic carbenes

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Abstract

The synthesis of N-heterocyclic carbene (NHC) adducts of copper(I) cyanate and copper(I) selenocyanate has been successfully achieved via the reaction of [Cu(NHC)Cl] with silver(I) cyanate and potassium selenocyanate respectively. Three copper(I) cyanate complexes [Cu(IXy)(NCO)] (1), [Cu(IPr)(NCO)] (2) and [Cu(SIPr)(NCO)] (3) [IXy = 1,3-bis(2,6-dimethylphenyl)imidazol-2-ylidene, IPr = 1,3- bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = 1,3-bis(2,6- diisopropylphenyl)imidazolin-2-ylidene] have been prepared and fully characterised. The X-ray crystal structures reveal the three complexes to be monomeric species in which the cyanate ligand is end-on, N-bound. These complexes, represent the first examples of monomeric copper(I) cyanate complexes. In addition, the copper(I) selenocyanate species [Cu(IPr)(NCSe)]2 (4) was prepared and fully characterised. The X-ray crystal structure reveals that a centrosymmetric dimer is formed with bridging selenocyanate ligands bound through both N and Se. This is in contrast to the monomeric structure observed in the previously reported and related complex [Cu(IPr)(NCS)]. Complex 4 represents a rare example of a stable dimeric adduct of copper(I) selenocyanate.
LanguageEnglish
Number of pages21
JournalEuropean Journal of Inorganic Chemistry
Publication statusAccepted/In press - 12 Jul 2019

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Cyanates
Copper
Crystal structure
Ligands
X rays
Silver
Dimers
carbene
selenocyanic acid

Keywords

  • copper
  • carbene ligands
  • x-ray diffraction
  • NMR spectroscopy

Cite this

@article{3ae82c45b4a64895b57b0e7c9e7a723d,
title = "Taming copper(I) cyanate and selenocyanate with N-heterocyclic carbenes",
abstract = "The synthesis of N-heterocyclic carbene (NHC) adducts of copper(I) cyanate and copper(I) selenocyanate has been successfully achieved via the reaction of [Cu(NHC)Cl] with silver(I) cyanate and potassium selenocyanate respectively. Three copper(I) cyanate complexes [Cu(IXy)(NCO)] (1), [Cu(IPr)(NCO)] (2) and [Cu(SIPr)(NCO)] (3) [IXy = 1,3-bis(2,6-dimethylphenyl)imidazol-2-ylidene, IPr = 1,3- bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = 1,3-bis(2,6- diisopropylphenyl)imidazolin-2-ylidene] have been prepared and fully characterised. The X-ray crystal structures reveal the three complexes to be monomeric species in which the cyanate ligand is end-on, N-bound. These complexes, represent the first examples of monomeric copper(I) cyanate complexes. In addition, the copper(I) selenocyanate species [Cu(IPr)(NCSe)]2 (4) was prepared and fully characterised. The X-ray crystal structure reveals that a centrosymmetric dimer is formed with bridging selenocyanate ligands bound through both N and Se. This is in contrast to the monomeric structure observed in the previously reported and related complex [Cu(IPr)(NCS)]. Complex 4 represents a rare example of a stable dimeric adduct of copper(I) selenocyanate.",
keywords = "copper, carbene ligands, x-ray diffraction, NMR spectroscopy",
author = "Dodds, {Christopher A} and Kennedy, {Alan R} and Ross Thompson",
year = "2019",
month = "7",
day = "12",
language = "English",
journal = "European Journal of Inorganic Chemistry",
issn = "1434-1948",

}

TY - JOUR

T1 - Taming copper(I) cyanate and selenocyanate with N-heterocyclic carbenes

AU - Dodds, Christopher A

AU - Kennedy, Alan R

AU - Thompson, Ross

PY - 2019/7/12

Y1 - 2019/7/12

N2 - The synthesis of N-heterocyclic carbene (NHC) adducts of copper(I) cyanate and copper(I) selenocyanate has been successfully achieved via the reaction of [Cu(NHC)Cl] with silver(I) cyanate and potassium selenocyanate respectively. Three copper(I) cyanate complexes [Cu(IXy)(NCO)] (1), [Cu(IPr)(NCO)] (2) and [Cu(SIPr)(NCO)] (3) [IXy = 1,3-bis(2,6-dimethylphenyl)imidazol-2-ylidene, IPr = 1,3- bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = 1,3-bis(2,6- diisopropylphenyl)imidazolin-2-ylidene] have been prepared and fully characterised. The X-ray crystal structures reveal the three complexes to be monomeric species in which the cyanate ligand is end-on, N-bound. These complexes, represent the first examples of monomeric copper(I) cyanate complexes. In addition, the copper(I) selenocyanate species [Cu(IPr)(NCSe)]2 (4) was prepared and fully characterised. The X-ray crystal structure reveals that a centrosymmetric dimer is formed with bridging selenocyanate ligands bound through both N and Se. This is in contrast to the monomeric structure observed in the previously reported and related complex [Cu(IPr)(NCS)]. Complex 4 represents a rare example of a stable dimeric adduct of copper(I) selenocyanate.

AB - The synthesis of N-heterocyclic carbene (NHC) adducts of copper(I) cyanate and copper(I) selenocyanate has been successfully achieved via the reaction of [Cu(NHC)Cl] with silver(I) cyanate and potassium selenocyanate respectively. Three copper(I) cyanate complexes [Cu(IXy)(NCO)] (1), [Cu(IPr)(NCO)] (2) and [Cu(SIPr)(NCO)] (3) [IXy = 1,3-bis(2,6-dimethylphenyl)imidazol-2-ylidene, IPr = 1,3- bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = 1,3-bis(2,6- diisopropylphenyl)imidazolin-2-ylidene] have been prepared and fully characterised. The X-ray crystal structures reveal the three complexes to be monomeric species in which the cyanate ligand is end-on, N-bound. These complexes, represent the first examples of monomeric copper(I) cyanate complexes. In addition, the copper(I) selenocyanate species [Cu(IPr)(NCSe)]2 (4) was prepared and fully characterised. The X-ray crystal structure reveals that a centrosymmetric dimer is formed with bridging selenocyanate ligands bound through both N and Se. This is in contrast to the monomeric structure observed in the previously reported and related complex [Cu(IPr)(NCS)]. Complex 4 represents a rare example of a stable dimeric adduct of copper(I) selenocyanate.

KW - copper

KW - carbene ligands

KW - x-ray diffraction

KW - NMR spectroscopy

M3 - Article

JO - European Journal of Inorganic Chemistry

T2 - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

SN - 1434-1948

ER -