Anion-dependent dimerization of a guanidiniocarbonyl pyrrole cation in DMSO |
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Authors: | Schmuck C Heil M |
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Affiliation: | Institut für Organische Chemie, Universit?t zu K?ln, Greinstrasse 4, 50939 K?ln, Germany. carsten.schmuch@uni-koeln.de |
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Abstract: | With spherical counteranions such as chloride or hexafluorophosphate, the glycine-derived guanidiniocarbonyl pyrrole cation 1 self-assembles into discrete dimers in DMSO, as can be seen by NMR and ESI mass spectral analysis. According to concentration- and temperature-dependent NMR studies, the dimerization is endothermic and therefore entropy driven. Molecular modeling suggests that the dimers are held together by hydrogen bonding in combination with pi-pi interactions. In the presence of picrate anions, dimerization of cation 1 does not occur, probably due to the formation of pi-stacked ion pairs. |
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