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Structures of piperazine, piperidine and morpholine

Parkin, A and Oswald, I D H and Parsons, S (2004) Structures of piperazine, piperidine and morpholine. Acta Crystallographica Section B: Structural Science, 60 (Part 2). pp. 219-227. ISSN 0108-7681

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The crystal structures of piperazine, piperidine and morpholine have been determined at 150 K. All three structures are characterized by the formation of NH...N hydrogen-bonded chains. In piperazine these are linked to form sheets, but the chains are shifted so that the molecules interleave. In morpholine there are in addition weak CH...O interactions. Topological analyses show that these three structures are closely related to that of cyclohexane-II, which can be described in terms of a pseudo-cubic close-packed array of molecules in a familiar ABC layered arrangement. While the positions of the molecules within each layer are similar, hydrogen bonding occurs between the ABC layers and in order to accommodate this the molecules are rotated relative to those in cyclohexane-II. Piperidine and morpholine also adopt layered structures, with hydrogen-bonding or CH...O interactions between the layers. In these cases, however, the layering more resembles a hexagonal close-packed arrangement.