Synthesis of Chiral Resorcinarene-based Hosts and a Mass Spectrometric Study of their Chemistry in Solution and the Gas Phase

Ngong Kodiah Beyeh, Domonkos Fehér, Minna Luostarinen, Christoph A. Schalley, Kari Rissanen

Research output: Contribution to journalArticleScientificpeer-review

18 Citations (Scopus)

Abstract

The syntheses and characterization of new chiral tetrabenzoxazine and tetrakis-(dialkylaminomethyl) resorcinarenes can be achieved through the reaction of resorcinarene with chiral amines and formaldehyde. In order to examine their host–guest chemistry, chiral quaternary ammonium guests were synthesized by methylation of different amines and amino acid methyl esters through a reductive methylation followed by addition of methyl iodide. Subsequent anion exchange of the iodide against tetraphenylborate helps to improve solubility of the salts in organic solvents. After characterization in solution, mass spectrometry is used to examine the resorcinarenes’ chemistry in the gas phase. Interesting implications of the fragmentation behavior for their solution phase chemistry arise, for which a first example is presented. Ammonium ion binding is indicated by mass spectrometry. Nevertheless, chiral recognition between the chiral hosts and pseudoracemic 1:1 mixtures of appropriately deuterium-labeled chiral guest cations is however not observed.
Original languageEnglish
Pages (from-to)381–394
JournalJOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
Volume56
Issue number3
DOIs
Publication statusPublished - Dec 2006
MoE publication typeA1 Journal article-refereed

Keywords

  • Electrospray Mass Spectrometry
  • gas-phase chemistry
  • resorcinarenes
  • host–guest chemistry
  • chirality

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