Issue 6, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Conformational and complexational study of some maleonitrile mixed oxadithia crown ethers by NMR spectroscopy and molecular modelling

Erich Kleinpeter,*a   Manuela Grotjahn,a   Karel D. Klika,b   Hans-Joachim Drexlerc  and  Hans-Jürgen Holdtc  

* Corresponding authors

a Institut für Organische Chemie und Strukturanalytik, Universität Potsdam, Potsdam, Germany

b Department of Chemistry, University of Turku, Turku, Finland

c Institut für Anorganische Chemie und Didaktik der Chemie, Universität Potsdam, Potsdam, Germany

Abstract

The macrocyclic ring interconversion of four maleonitrile mixed oxadithia crown ethers of variable ring size, mn-12-S2O2, mn-15-S2O3, mn-18-S2O4 and fn-12-S2O2, were studied by 1H and 13C NMR spectroscopy and by molecular modelling. The barriers to ring interconversion were estimated using variable temperature NMR spectroscopy and from the calculated activation energies, together with the spin-lattice relaxation times of the CH2 carbon atoms, conclusions were drawn regarding the intramolecular flexibility of the crown ethers in both the free state as well as the complexed state incorporating either AgI, BiIII, SbIII, PdII or PtII metal cations. Furthermore, both the stoichiometry of the complexes and the coordination sites of the crown ethers to the various cations were also clearly implicated. Molecular modelling was also utilised to ascertain the preferred conformers of the four compounds and their corresponding complexes, the results of which corroborated the experimental NMR results to a high degree.

Graphical abstract: Conformational and complexational study of some maleonitrile mixed oxadithia crown ethers by NMR spectroscopy and molecular modelling

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Article information

DOI
https://doi.org/10.1039/B009453F
Article type
Paper
Submitted
24 Nov 2000
Accepted
06 Apr 2001
First published
01 May 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 988-993

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Conformational and complexational study of some maleonitrile mixed oxadithia crown ethers by NMR spectroscopy and molecular modelling

E. Kleinpeter, M. Grotjahn, K. D. Klika, H. Drexler and H. Holdt, J. Chem. Soc., Perkin Trans. 2, 2001, 988 DOI: 10.1039/B009453F

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