Anion-Dependent Dimerization of a Guanidiniocarbonyl Pyrrole Cation in DMSO
- 4 April 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (9) , 1253-1256
- https://doi.org/10.1021/ol015596p
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.Keywords
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