Noncovalent complex formation of tetratosylated resorcarene with aromatic, aliphatic, and cyclic alkyl ammonium ions: a mass spectrometric study of complex properties

Abstract

The ability of tetratosylated resorcarene to form complexes with aromatic ammonium ions was investigated by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. The formation of noncovalent complexes, [1þguest] þ and, as observed with singly charged aromatic anilinium and phenylene aminoammonium guests. Comparison of the complexation efficiencies of the aromatic and aliphatic ammonium ions showed the importance of proton affinity of conjugate amines in complex formation. In collision-induced dissociation experiments, gas-phase stability was found to be lower for complexes formed with aromatic ions and this behavior was not found to depend on the proton affinity of conjugate amines. Fast oxidation of the para and ortho aminoammonium ions and complexation of these ions with tetratosylated resorcarene was observed.

Complex formation between a tetramesityl sulfonated resorcarene and alkylammonium ions: a mass spectrometric study of noncovalent interactions

“…1). 17–19 The results implied that the guest ions are situated at the stern of the boat conformation of the resorcarene and have a hydrogen‐bonding interaction with the SO groups of the host. Our main purpose in the present study was to examine the complexation behavior of sterically more hindered tetramesityl sulfonated resorcarene and compare it with that of tetratosylated resorcarene to see whether the methyl groups of the mesityl substituents had an effect on the complex formation and properties.…”