Sulfurane 5b with solubility enhancing substituents has been synthesized to be used as an AAAA recognition site in quadruple hydrogen bond heterodimers. A complementary DDDD partner [4b + H+] has been generated from a DDAD domain 4b by protonation. The association constant for the heterodimer complex formation has been determined by NMR titration in chloroform.
Resonance enhanced multi-photon ionization-reflectron time of flight mass spectrometry is the analytical method of choice to observe hydrogen bonded supramolecules in the gas phase when protonation of basic centers competes with cluster formation.
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