Synthesis and self-association properties of flexible guanidiniocarbonylpyrrole-carboxylate zwitterions in DMSO: intra-versus intermolecular ion pairing

C Schmuck, T Rehm, L Geiger…

Index: Schmuck, Carsten; Rehm, Thomas; Geiger, Lars; Schaefer, Mathias Journal of Organic Chemistry, 2007 , vol. 72, # 16 p. 6162 - 6170

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Citation Number: 29

Abstract

We have synthesized a new class of flexible zwitterions 6a-e, in which a carboxylate is linked via an alkyl chain with variable length (one to five methylene groups) to a guanidiniocarbonylpyrrole cation. The self-association properties of these zwitterions were determined by NMR dilution studies in DMSO and by ESI-MS experiments. The stability and hence also the size of the aggregates formed via self-assembly is critically dependent on ...