Abstract
A theoretical study of the hydrogen bond (HB) and halogen bond (XB) complexes between 1-halo-closo-carboranes and hydrogen cyanide (NCH) as HB and XB probe has been carried out at the MP2 computational level. The energy results show that the HB complexes are more stable than the XBs for the same system, with the exception of the isoenergetic iodine derivatives. The analysis of the electron density with the quantum theory of atoms in molecules (QTAIM) shows the presence of a unique intermolecular bond critical point with the typical features of weak noncovalent interactions (small values of the electron density and positive Laplacian and total energy density). The natural energy decomposition analysis (NEDA) of the complexes shows that the HB and XB complexes are dominated by the charge-transfer and polarization terms, respectively. The work has been complemented with a search in the CSD database of analogous complexes and the comparison of the results, with those of the 1-halobenzene:NCH complexes showing smaller binding energies and larger intermolecular distances as compared to the 1-halo-closo-carboranes:NCH complexes.
Highlights
The most important noncovalent interaction is, without doubt, the hydrogen bond
The natural energy decomposition analysis (NEDA) of the complexes shows that the hydrogen bond (HB) and XB complexes are dominated by the charge-transfer and polarization terms, respectively
The work has been complemented with a search in the Cambridge Structural Database (CSD) database of analogous complexes and the comparison of the results, with those of the 1-halobenzene:NCH complexes showing smaller binding energies and larger intermolecular distances as compared to the 1-halo-closo-carboranes:NCH complexes
Summary
The most important noncovalent interaction is, without doubt, the hydrogen bond. in recent years other interactions [1] have been described in various studies. In the last years of the 20th century, systematic studies of the gas phase and its comparison with analogous hydrogen bonds were carried out, mainly by Legon and co-workers [3]. In this century, the properties of the halogen bond have found applications in the fields of drug design [4,5,6], material science [7,8,9] and organocatalysis [10,11,12].
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