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The σ‐hole concept elicits obvious parallels between the halogen bond and the hydrogen bond (Figure 1.1). As such, halogen bond studies, as well as concepts and nomenclature, were undoubtedly inspired by decades of hydrogen bond research. Similarities have prompted frequent comparison between the two, many of which are discussed in the following sections and ensuing chapters. A motivation of these comparative studies has been to discover the limits and unique features of this “new” noncovalent interaction. As such, studies in solution, solid state, and in silico have already demonstrated promising features of the halogen bond compared with its hydrogen analogue.