A statistical analysis of halide ⋯ H-A (A = OR, NR2, N+R3) hydrogen bonding interactions in the solid state

Mark Mascal

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44 Scopus citations


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 languageEnglish (US)
Pages (from-to)1999-2001
Number of pages3
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number10
StatePublished - Oct 1997
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)


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