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Reactions of N-heterocyclic carbene-based Chalcogenoureas with Halogens: a diverse range of outcomes

Reactions of N-heterocyclic carbene-based Chalcogenoureas with Halogens: a diverse range of outcomes

Saab, Marina, Nelson, David J., Leech, Matthew C., Lam, Kevin ORCID: 0000-0003-1481-9212, Nolan, Steven P., Nahra, Fady and Hecke, Kristof Van (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 (Print), 1520-586X (Online) (doi: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 were obtained. Cyclic voltammetry was carried out to characterize the oxidation and reduction potentials of these [E(NHC)] species; selenoureas were found to be easier to oxidize 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 moiety. The reactivity of these chalcogenoureas with different halogenating reagents (Br2, SO2Cl2, I2) was then investigated, and products were characterized 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.

Item Type: Article
Uncontrolled Keywords: carbenes, electrosynthesis, analytical chemistry, electrochemical methods
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 16 May 2022 15:58
URI: http://gala.gre.ac.uk/id/eprint/35172

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