Nature of Carbon–Halogen Bonds

This paper is a critical review of the literature on the problem of the nature of carbon–halogen bonds. It examines the various physical properties of halogen-containing organic compounds which are useful in discussing the problem of the chemical bond (infrared spectra, dipole moments, interatomic distances, nuclear quadrupole interaction constants, nuclear magnetic resonance). Special attention is paid to results from nuclear magnetic resonance, which show the uselessness of treating the properties of organohalogen compounds from the position of mesomerism–resonance theory. The correlation between the chemical shifts of nuclear magnetic resonance and the σ-constants of the substituents in various organohalogen compounds is considered. Attention is paid to the hybridisation of the orbitals of the carbon and halogen atoms and to the associated electronic displacements in unsaturated and aromatic systems.
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