On the isomerization of cyclooctyne into cycloocta-1,3-diene: synthesis, characterization and structure of a dinuclear platinum(II) complex with a μ-η2:η2-1,3-COD ligand

Dalton Transactions : an International Journal of Inorganic Chemistry
Anja KönigDirk Steinborn

Abstract

The Zeise's salt type cyclooctyne compound [K(18C6)][PtCl(3)(COC)] (1; COC = cyclooctyne; 18C6 = 18-crown-6) was found to react in chloroform solution at room temperature within several weeks yielding the dinuclear cyclooctadiene compound [K(18C6)](2)[(PtCl(3))(2)(μ-η(2):η(2)-1,3-COD)] (2; 1,3-COD = cycloocta-1,3-diene) and non-coordinated cycloocta-1,3-diene. The identity of 2 was confirmed by microanalysis, NMR spectroscopy ((1)H, (13)C) and electrospray ionization mass spectrometry (ESI-MS). A single-crystal X-ray diffraction analysis of 2 exhibited a bridging μ-η(2):η(2)-cycloocta-1,3-diene ligand with non-conjugated double bonds each coordinated to a PtCl(3) fragment. On the basis of DFT calculations as well as energy decomposition analyses (EDA), charge decomposition analyses (CDA) and natural bond orbital (NBO) analyses the peculiarities of the nature of the Pt-C bonds in the dinuclear complex anion [(PtCl(3))(2)(μ-η(2):η(2)-1,3-COD)](2-) (2a') compared with those in mononuclear olefin complexes of Zeise's salt type [PtCl(3)L](-) (L = η(2)-1,3-COD, 3a'; cis-but-2-ene, 4a'; COE, 5a'; COE = cyclooctene) are discussed. Furthermore, the driving force for the strongly exergonic reaction with formation of the cyclooctadiene co...Continue Reading

References

Dec 26, 2001·Chemical Reviews·G Frenking, N Fröhlich
Oct 19, 2006·Chemical Communications : Chem Comm·Ryo ShintaniTamio Hayashi
Sep 27, 2007·Chemistry : a European Journal·Dirk Steinborn, Sebastian Schwieger
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Apr 1, 1986·Journal of Computational Chemistry·Michael J S Dewar, Charles H Reynolds

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Citations

Apr 14, 2016·Angewandte Chemie·Michael J ButlerMark R Crimmin

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