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

Marina Saab, David James Nelson, Matthew C. C Leech, Kevin Lam, Steven P Nolan, Fady Nahra, Kristof Van Hecke

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)
53 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)3721-3733
Number of pages13
JournalDalton Transactions
Volume51
Issue number9
Early online date10 Feb 2022
DOIs
Publication statusPublished - 7 Mar 2022

Keywords

  • reactions
  • N-heterocyclic carbene-based chalcogenoureas
  • halogens
  • diverse range of outcomes
  • [E(NHC)]

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