Issue 38, 2013
From the journal:

RSC Advances

New cycloimmonium ylide ligands and their palladium(ii) affinities†

Rodica Postolachi,a   Ramona Danac,*a   Niklaas J. Buurma,c   Aurel Pui,a   Mihaela Balan,b   Sergiu Shovab  and  Calin Deleanub  

* Corresponding authors

a Alexandru Ioan Cuza University of Iasi Chemistry Department, 14 Carol I, Iasi 700506, Romania
E-mail: rdanac@uaic.ro
Fax: +40232201313
Tel: +40232201342

b Petru Poni Institute of Macromolecular Chemistry, 41A Grigore Ghica Voda Alley, Iasi 700487, Romania
E-mail: shova@icmpp.ro
Fax: +40232211299
Tel: +40232421230

c Physical Organic Chemistry Centre, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff CF10 3AT, UK
E-mail: Buurma@Cardiff.ac.uk

Abstract

Ten new stable 4-(4′-pyridyl)pyridinium disubstituted monoylides were synthesized by the reaction of 4-(4′-pyridyl)pyridinium monosubstituted ylides with electrophiles as aromatic isocyanates and isothiocyanates. The facile synthesis and high stability of the new ylides were attributed not only to the delocalization of both negative and positive charges, but also to the intramolecular hydrogen bond. This bond was proved to be present both in solution (by NMR) and solid phase (by X-ray crystallography). The computational studies using density functional theory calculations (DFT) suggest, as well, an important charge delocalization in gas-phase structures for simplified model disubstituted cycloimmonium ylides. The palladium complexation for two of the new ylides was studied using NMR titrations and quantified using UV-visible spectroscopy titrations.

Graphical abstract: New cycloimmonium ylide ligands and their palladium(ii) affinities

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Article information

DOI
https://doi.org/10.1039/C3RA41911H
Article type
Paper
Submitted
18 Apr 2013
Accepted
09 Jul 2013
First published
10 Jul 2013

RSC Adv., 2013,3, 17260-17270

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New cycloimmonium ylide ligands and their palladium(II) affinities

R. Postolachi, R. Danac, N. J. Buurma, A. Pui, M. Balan, S. Shova and C. Deleanu, RSC Adv., 2013, 3, 17260 DOI: 10.1039/C3RA41911H

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