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Halogen bonding versuschalcogen and pnicogen bonding: a combined Cambridge structural database and theoretical study

2012; Royal Society of Chemistry; Volume: 15; Issue: 16 Linguagem: Inglês

10.1039/c2ce26741a

1466-8033

Antonio Bauzá, David Quiñonero, Pere M. Deyà, Antonio Frontera,

Nonlinear Optical Materials Research

In this manuscript we analyze the Cambridge Structural Database (CSD) to compare the relative importance of halogen, chalcogen and pnicogen bonding. The three interactions can be explained in terms of electrostatic effects, considering the halogen, chalcogen or pnicogen as a Lewis acid due to the presence of a sigma hole (σ-hole). We have studied the behaviour of the three interactions considering two types of Lewis bases: amines and arenes. Combining the CSD search and a comprehensive theoretical study (DFT-D3) we conclude that the halogen bonding interaction is the energetically most favourable when the electron donor is an amine. In contrast, the pnicogen bond is the most favourable if the Lewis base is benzene (pnicogen–π interaction).