Neutral alkaline-metal and alkaline-earth-metal derivatives of imidazole and benzimidazole
Date
2014
Authors
Blanco, F.
Lloyd, D.G.
Alkorta, I.
Elguero, J.
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Journal article
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Journal of Physical Chemistry A, 2014; 118(23):4195-4204
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Abstract
A theoretical study of the minima and connecting transition states of the neutral complexes formed by alkaline-metal and alkaline-earth-metal derivatives of imidazolate and benzimidazolate anions has been carried out using B3LYP/6-31+G(d,p), B3LYP/6-311+G(3df,2p), and G3B3 methods. Two and three nondegenerated minima and two and four TS structures have been identified for imidazole and benzimidazole derivatives, respectively. The most stable minima of the alkaline-metal derivatives of both systems correspond to the metal interacting with the imidazole ring, whereas in the alkaline-earth-metal derivatives, the preferred minima depend on the substituent. A remarkable feature of some minima is the fact that some of the metal−aromatic interactions follow the classical π−cation pattern, even though the global structure corresponds to a neutral salt, constituting a class of noncovalent interaction of great interest in the chemistry of aromatic and heterocyclic complexes. A CSD search has confirmed that the two bonding modes, N−σ and π, are present in the solid phase. The π mode has been analyzed by comparison with other azoles.
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Data source: suporting information, https://doi.org/10.1021/jp502443h
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Copyright 2014 American Chemical Society