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Hydrogen Bonding of two 1-(ω-Ammonioalkyl)-2-acyl-cyclopentadienides in the Solid State

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Hydrogen Bonding of two 1-( ω -Ammonioalkyl)-2-acyl-cyclopentadienides in the Solid State

Andreas Müller and Gerhard Maas

Abteilung Organische Chemie I, Universität Ulm, D-89069 Ulm, Germany Reprint requests to Prof. Dr. G. Maas. E-mail:gerhard.maas@chemie.uni-ulm.de Z. Naturforsch.55b, 541Ð545 (2000); received April 13, 2000

Cyclopentadienides, Hydrogen Bonding, Zwitter Ions

The solid-state structures of a 1-(ω-ammoniopropyl)-2-(2-thienylcarbonyl)-cyclopenta- dienide (2) and a 1-(ω-ammoniopentyl)-2-(4-methoxybenzoyl)-cyclopentadienide (3) have been determined. Both betaines self-assemble by NH ··· O hydrogen bonds, but the motifs are different. In the ammoniopropyl case, both intramolecular and intermolecular hydrogen bonds of this type exist, the latter bond being responsible for the formation of infinite chains.

In the ammoniopentyl case, intermolecular hydrogen bonds build up a two-dimensional net- work which contains centrosymmetric dimers held together by NH ··· O=C-aryl hydrogen bonds.

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