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J Phys Chem A. 2014 Jun 12;118(23):4195-204. doi: 10.1021/jp502443h. Epub 2014 Jun 3.

Neutral alkaline-metal and alkaline-earth-metal derivatives of imidazole and benzimidazole.

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1
Molecular Design Group, School of Biochemistry and Immunology, University of Dublin, Trinity College , Dublin 2, Ireland.

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.

PMID:
24844848
DOI:
10.1021/jp502443h
[Indexed for MEDLINE]
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