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Inorganics 2014, 2(4), 620-648; doi:10.3390/inorganics2040620

Experimental and Theoretical Studies of the Factors Affecting the Cycloplatination of the Chiral Ferrocenylaldimine (SC)-[(η5-C5H5)Fe{(η5-C5H4)–C(H)=N–CH(Me)(C6H5)}]

1
Departament de Química Inorgánica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11. E-08028 Barcelona, Spain
2
Unitat de Difracció de Raigs-X, Centre Científic i Tecnològic de la Universitat de Barcelona, Solé i Sabarís 1-3, E-08028 Barcelona, Spain
3
Biomed Division, Leitat Tecnological Center, Parc Científic de Barcelona, Edifici Hèlix, C/Baldiri i Reixach, 15-21, E-08028 Barcelona, Spain
*
Authors to whom correspondence should be addressed.
Received: 31 July 2014 / Revised: 8 October 2014 / Accepted: 10 October 2014 / Published: 6 November 2014
(This article belongs to the Special Issue Organoplatinum Complexes)
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Abstract

The study of the reactivity of the enantiopure ferrocenyl Schiff base (SC)-[FcCH=N–CH(Me)(C6H5)] (1) (Fc = (η5-C5H5)Fe(η5-C5H4)) with cis-[PtCl2(dmso)2] under different experimental conditions is reported. Four different types of chiral Pt(II) have been isolated and characterized. One of them is the enantiomerically pure trans-(SC)-[Pt{κ1-N[FcCH=N–CH(Me)(C6H5)]}Cl2(dmso)] (2a) in which the imine acts as a neutral N-donor ligand; while the other three are the cycloplatinated complexes: [Pt{κ2-C,N [(C6H4)–N=CHFc]}Cl(dmso)] (7a) and the two diastereomers {(Sp,SC) and (Rp,SC)} of [Pt{κ2-C,N[(η5-C5H3)–CH=N–{CH(Me)(C6H5)}]Fe(η5-C5H5)}Cl(dmso)] (8a and 9a, respectively). Isomers 7a-9a, differ in the nature of the metallated carbon atom [CPh (in 7a) or CFc (in 8a and 9a)] or the planar chirality of the 1,2-disubstituted ferrocenyl unit (8a and 9a). Reactions of 7a9a with PPh3 gave [Pt{κ2-C,N[(C6H4)–N=CHFc]}Cl(PPh3)] (in 7b) and the diastereomers (Sp,SC) and (Rp,SC) of [Pt{κ2-C,N[(η5-C5H3)–CH=N–{CH(Me)(C6H5)}] Fe(η5-C5H5)}Cl(PPh3)] (8b and 9b, respectively). Comparative studies of the electrochemical properties and cytotoxic activities on MCF7 and MDA-MB231 breast cancer cell lines of 2a and cycloplatinated complexes 7b-9b are also reported. Theoretical studies based on DFT calculations have also been carried out in order to rationalize the results obtained from the cycloplatination of 1, the stability of the Pt(II) complexes and their electrochemical properties. View Full-Text
Keywords: platinacycles; chiral platinum(II) complexes; DFT calculations; biological activity; electrochemistry platinacycles; chiral platinum(II) complexes; DFT calculations; biological activity; electrochemistry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

López, C.; Bosque, R.; Pujol, M.; Simó, J.; Sevilla, E.; Font-Bardía, M.; Messeguer, R.; Calvis, C. Experimental and Theoretical Studies of the Factors Affecting the Cycloplatination of the Chiral Ferrocenylaldimine (SC)-[(η5-C5H5)Fe{(η5-C5H4)–C(H)=N–CH(Me)(C6H5)}]. Inorganics 2014, 2, 620-648.

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