Reactions of N-heterocyclic carbene-based chalcogenoureas with halogens : a diverse range of outcomes

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Saab, Marina and Nelson, David James and Leech, Matthew C. C and Lam, Kevin and Nolan, Steven P and Nahra, Fady and Van Hecke, Kristof (2022) Reactions of N-heterocyclic carbene-based chalcogenoureas with halogens : a diverse range of outcomes. Dalton Transactions, 51 (9). pp. 3721-3733. ISSN 1477-9226 (https://doi.org/10.1039/D2DT00010E)

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Abstract

We have investigated the reactions of chalcogenoureas derived from N-heterocyclic carbenes, referred to here as [E(NHC)], with halogens. Depending on the structure of the chalcogenourea and the identity of the halogen, a diverse range of reactivity was observed and a corresponding range of structures was obtained. Cyclic voltammetry was carried out to characterise the oxidation and reduction potentials of these [E(NHC)] species; selenoureas were found to be easier to oxidise than the corresponding thioureas. In some cases, a correlation was found between the oxidation potential of these compounds and the electronic properties of the corresponding NHC. The reactivity of these chalcogenoureas with different halogenating reagents (Br2, SO2Cl2, I2) was then investigated, and products were characterised using NMR spectroscopy and single-crystal X-ray diffraction. X-ray analyses elucidated the solid-state coordination types of the obtained products, showing that a variety of possible adducts can be obtained. In some cases, we were able to extrapolate a structure/activity correlation to explain the observed trends in reactivity and oxidation potentials.

ORCID iDs

Saab, Marina, Nelson, David James ORCID logoORCID: https://orcid.org/0000-0002-9461-5182, Leech, Matthew C. C, Lam, Kevin, Nolan, Steven P, Nahra, Fady and Van Hecke, Kristof;
  • Item type:Article
    ID code:79566
    Dates:
    Date
    Event
    7 March 2022
    Published
    10 February 2022
    Published Online
    7 February 2022
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:11 Feb 2022 18:00
    Last modified:12 Dec 2024 17:29
    URI:https://strathprints.strath.ac.uk/id/eprint/79566
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