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Synthesis, self‐association and chiroselectivity of isotopically labeled trianglamine macrocycles in the ion trap mass spectrometer
Author(s) -
Kuhnert Nikolai,
LeGresley Adam,
Nicolau Daniel C.,
LopezPeriago Ana
Publication year - 2007
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1449
Subject(s) - chemistry , ion trap , mass spectrometry , dimer , electrospray , gas phase , ion , electrospray ionization , analytical chemistry (journal) , organic chemistry , chromatography
The synthesis and self‐association of chiral isotopically labeled trianglamine macrocycles under electrospray mass spectrometer conditions in an ion trap are described. A moderate diastereoselectivity in the self‐association process was observed providing a synthetic model system for the investigation of chiral self‐association in the gas phase. The first non‐covalently bound dimer exclusively bonded through aromatic–aromatic interactions was observed in the gas phase. Evidence for self‐association in solution was observed by diffusion nuclear magnetic resonance spectroscopy. Copyright © 2007 John Wiley & Sons, Ltd.