biostudies-literatureAl Sheakh LDeutsche Forschungsgemeinschaft (DFG, German Science Foundation - LU-506/12-2LU-506/14-21850-1856https://www.ebi.ac.uk/biostudies/studies/S-EPMC8518508biostudies-literatureUnknown22(18)The paradigm of supramolecular chemistry relies on the delicate balance of noncovalent forces. Here we present a systematic approach for controlling the structural versatility of halide salts by the nature of hydrogen bonding interactions. We synthesized halide salts with hydroxy-functionalized pyridinium cations [HOC_n Py]⁺ (n=2, 3, 4) and chloride, bromide and iodide anions, which are typically used as precursor material for synthesizing ionic liquids by anion metathesis reaction. The X-ray structures of these omnium halides show two types of hydrogen bonding: 'intra-ionic' H-bonds, wherein the anion interacts with the hydroxy group and the positively charged ring at the same cation, and 'inter-ionic' H-bonds, wherein the anion also interacts with the hydroxy group aChemphyschem : a European journal of chemical physics and physical chemistryThree in One: The Versatility of Hydrogen Bonding Interaction in Halide Salts with Hydroxy-Functionalized Pyridinium Cations.PMC8518508286149019269854963Villinger AStange PNiemann TAl Sheakh LZaitsau DHLudwig RStrate AfalseThree in One: The Versatility of Hydrogen Bonding Interaction in Halide Salts with Hydroxy-Functionalized Pyridinium Cations.The paradigm of supramolecular chemistry relies on the delicate balance of noncovalent forces. Here we present a systematic approach for controlling the structural versatility of halide salts by the nature of hydrogen bonding interactions. We synthesized halide salts with hydroxy-functionalized pyridinium cations [HOC_n Py]⁺ (n=2, 3, 4) and chloride, bromide and iodide anions, which are typically used as precursor material for synthesizing ionic liquids by anion metathesis reaction. The X-ray structures of these omnium halides show two types of hydrogen bonding: 'intra-ionic' H-bonds, wherein the anion interacts with the hydroxy group and the positively charged ring at the same cation, and 'inter-ionic' H-bonds, wherein the anion also interacts with the hydroxy group a2021-01-01T00:00:00Z2021 Sep2025-04-04T10:55:41.269Z2025-04-04T10:55:41.269ZS-EPMC85185083424194610.1002/cphc.202100424