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Unusual complex between 18-Crown-6 and tetramethylammonium cation—detection by electrospray ionization mass spectrometry

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Abstract

Complexes between crown ethers and quaternary ammonium cations have been studied by electrospray ionisation mass spectrometry (ESI-MS). The ESI-MS method has been shown to allow observation of not only stable inclusion complexes between large crown ethers and tetramethylammonium cation (e.g. [DB30C10 + (CH3)4N]+ ion) but also of unstable inclusion complexes between smaller crown ethers and quaternary ammonium cations which are difficult to observe by other methods, namely [18C6 + (CH3)4N]+ ion. Stability of the complexes between crown ethers containing aromatic ring and tetramethylammonium cation is enhanced by cation-Π interactions. The molecule of 18C6 does not contain aromatic rings, thus [18C6 + (CH3)4N]+ ion exists due to the formation of C–H···O hydrogen bonds. Such a complex is quite unusual, since C–H···O hydrogen bonds are very weak and usually coexist with other strong interactions.

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  1. Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780, Poznań, Poland

    Rafał Frański & Błażej Gierczyk

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  1. Rafał Frański
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  2. Błażej Gierczyk
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Correspondence to Rafał Frański.

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Frański, R., Gierczyk, B. Unusual complex between 18-Crown-6 and tetramethylammonium cation—detection by electrospray ionization mass spectrometry. J Incl Phenom Macrocycl Chem 62, 339–343 (2008). https://doi.org/10.1007/s10847-008-9476-7

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  • DOI: https://doi.org/10.1007/s10847-008-9476-7

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