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


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Article Info

DATE

2006-12

AUTHORS

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

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. More... »

PAGES

381-394

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10847-006-9121-2

DOI

http://dx.doi.org/10.1007/s10847-006-9121-2

DIMENSIONS

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45 schema:description 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.
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