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Issue 8, 2018
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Boron–boron, carbon–carbon and nitrogen–nitrogen bonding in N-heterocyclic carbenes and their diazaboryl and triazole analogues: Wanzlick equilibrium revisited

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Abstract

A series of monomers and dimers of N-heterocyclic carbenes and their diazaboryl and triazole analogues were investigated using the M06-2X and M06 density functional methods as well as using a DLPNO-CCSD(T) approach. We show that asymmetric carbenes bearing a benzyl and a mesityl moiety are predicted to form stable dimers due to favorable off-centre parallel stacking interactions. We also show that the double bond of the imidazole core destabilizes carbene dimers, shifting the Wanzlick equilibrium towards monomers. We predict that the methyl-, ethyl- and mesityl-substituted diazaboroles are more stable as monomers, irrespective of the presence of the double-bond in their structure, as are triazoles. Additionally, we demonstrate that the HOMO–LUMO gap difference between the monomer and the dimer, which is relatively easy to obtain, is a good indicator of the relative stability of the dimer versus the monomer for carbenes.

Graphical abstract: Boron–boron, carbon–carbon and nitrogen–nitrogen bonding in N-heterocyclic carbenes and their diazaboryl and triazole analogues: Wanzlick equilibrium revisited

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Publication details

The article was received on 17 Jan 2018, accepted on 14 Mar 2018 and first published on 16 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00296G
Citation: New J. Chem., 2018,42, 6183-6190
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    Boron–boron, carbon–carbon and nitrogen–nitrogen bonding in N-heterocyclic carbenes and their diazaboryl and triazole analogues: Wanzlick equilibrium revisited

    K. Młodzikowska, A. A. Rajkiewicz, K. Grela and B. Trzaskowski, New J. Chem., 2018, 42, 6183
    DOI: 10.1039/C8NJ00296G

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