30 No. 6
Nomenclature for Rotaxanes and Pseudorotaxanes (IUPAC Recommendations 2008)
Andrey Yerin, Edward S. Wilks, Gerard P. Moss, and Akira Harada
Pure and Applied Chemistry, 2008
Vol. 80, No. 9, pp. 2041–2068
|A Type 2.2 pseudorotaxane with symmetrical
components. Isomers are not possible.
Rotaxanes were first represented pictorially in 1958 as in situ intermediates in the synthesis of catenanes. Rotaxanes were proposed as a new type of species (though not referred to as pseudorotaxanes or rotaxanes) in 1961, and shown to exist in 1967. However, it was not until 1971 that Schill introduced a nomenclature system for rotaxanes. In 2000, Vögtle and coworkers proposed a generic nomenclature system in which Schill’s description was extended to include information about mechanical or covalent linkages within the components of the rotaxane to distinguish between intermolecular and intramolecular rotaxanes. Nevertheless, the proposed nomenclature cannot unambiguously describe the whole range of rotaxane structures reported in the literature.
This article specifies a systematic nomenclature for rotaxanes that includes the description of structure, composition, and isomerism of rotaxanes. This article discusses only rotaxanes in which none of the components is macromolecular, but the naming principles specified also can be used to name macromolecular rotaxanes. Specific recommendations for naming rotaxanes with at least one polymeric component will be published in a separate document.
Because the structures of rotaxanes are often large, in most cases throughout this article schematic presentations of rotaxanes and their components are used. Full chemical structures of rotaxanes and their systematic names are given.
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