The interaction between F-, Cl-, Br- and I- and organic H-bond donors OH, NH and N+H are examined in detail using the Cambridge Structural Database. The ammonium group is shown to be the most effective H-bond donor to the halides, followed by the hydroxy group and neutral NH. Comparison of the H-bonding requirements of the anions in each case shows trends in X- ⋯ HA distances (r), with the Δr interval between F- and Cl- being the greatest, and that between Cl- and Br- the least. Mean H-bonding angles 〈LAHX- are ca. 160° and tend towards greater linearity with increasing quality of the hydrogen bond. Interactions of halide ions with macrocyclic H-bonding receptors and the potential for host selectivity are discussed.
|Original language||English (US)|
|Number of pages||3|
|Journal||Journal of the Chemical Society. Perkin Transactions 2|
|Publication status||Published - Oct 1997|
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