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Issue 16, 2013
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Linear free energy relationships in halogen bonds

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Abstract

Four models of halogen bonds were used to quantify this bond using the DFT B97D/6-311+G(d) computational level: para-substituted iodobenzenes, para- and meta-substituted bromobenzenes complexed with three simple Lewis bases (NH3, NCH and CNH), 1-bromo-4-substituted-bicyclo[2.2.2]octanes with NH3 and 3- and 4-substituted pyridines complexed with BrCl and BrF. In addition, the combination of the para-substituted bromobenzenes with the 4-substituted pyridines has been studied. A total of 459 complexes have been optimized and are discussed in the present article. The energetic and geometric results have been analyzed based on the properties of the substituents and the isolated molecules involved in the interaction. The Hammett–Taft parameters provide reasonable correlations with the interaction energies. However, excellent correlations are obtained in all the cases when the electrostatic properties of the two molecules involved in the interaction are considered (R2 > 0.99).

Graphical abstract: Linear free energy relationships in halogen bonds

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Publication details

The article was received on 31 Oct 2012, accepted on 21 Dec 2012 and first published on 21 Dec 2012


Article type: Paper
DOI: 10.1039/C2CE26786A
Citation: CrystEngComm, 2013,15, 3178-3186
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    Linear free energy relationships in halogen bonds

    I. Alkorta, G. Sánchez-Sanz and J. Elguero, CrystEngComm, 2013, 15, 3178
    DOI: 10.1039/C2CE26786A

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