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Formation of Complex Ions03:45

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A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
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Kinetic Studies and Significance
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An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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On the reactivity of complexes [Ni(NHC)2] with CS2.

Martin Simon Luff1, Celine Sophie Corsei1, Udo Radius1

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The reaction of nickel complexes with carbon disulfide (CS2) yields diverse products depending on the N-heterocyclic carbene (NHC) ligand. Sterically demanding NHCs lead to unique dinuclear complexes, while others form bis-dithiocarboxylate structures.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Nickel complexes with N-heterocyclic carbene (NHC) ligands are versatile synthons in catalysis and materials science.
  • Carbon disulfide (CS2) is a reactive heterocumulene with diverse coordination modes.

Purpose of the Study:

  • To investigate the reactivity of [Ni(NHC)2] synthons with carbon disulfide (CS2).
  • To explore the influence of different N-heterocyclic carbene (NHC) ligands on the reaction outcome.
  • To characterize the resulting nickel-carbon disulfide complexes.

Main Methods:

  • Synthesis of nickel complexes with various NHC ligands.
  • Reaction of nickel precursors with carbon disulfide (CS2).
  • Isolation and characterization of products using spectroscopic and crystallographic techniques.

Main Results:

  • [Ni(NHC)2(η2-CS2)] complexes were formed with IiPrMe and IiPr NHCs.
  • Dinuclear complexes, [{Ni(IMes)(μ2-CS2)}2] and [{Ni(IDipp)(μ2-CS2)}2], resulted from sterically demanding IMes and IDipp NHCs, respectively.
  • Insertion of CS2 into Ni-cAAC bonds yielded bis-(azolium-2-dithiocarboxylate) complexes [Ni(cAACMe-CS2)2] when using cAACMe.

Conclusions:

  • The outcome of the reaction between [Ni(NHC)2] and CS2 is highly dependent on the steric and electronic properties of the NHC ligand.
  • Diverse nickel-CS2 coordination modes and complex architectures can be achieved by tuning the NHC ligand.
  • This study highlights the rich reactivity of nickel-NHC complexes with carbon disulfide, offering pathways to novel organometallic structures.