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Bisguanidines with biphenyl, binaphthyl, and bipyridyl cores: proton-sponge properties and coordination chemistry

Herein, we report on the synthesis, protonation, and coordination chemistry of chelating guanidine ligands with biphenyl, binaphthyl, and bipyridyl backbones. The ligands are shown to be proton sponges, and this protonation was studied experimentally and by using quantum-chemical calculations. Group...

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Bibliographic Details
Main Authors: Maronna, Astrid Christine (Author) , Hübner, Olaf (Author) , Enders, Markus (Author) , Kaifer, Elisabeth (Author) , Himmel, Hans-Jörg (Author)
Format: Article (Journal)
Language:English
Published: May 22, 2013
In: Chemistry - a European journal
Year: 2013, Volume: 19, Issue: 27, Pages: 8958-8977
ISSN:1521-3765
DOI:10.1002/chem.201204294
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201204294
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201204294
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Author Notes:Astrid Maronna, Olaf Hübner, Markus Enders, Elisabeth Kaifer, and Hans-Jörg Himmel
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Summary:Herein, we report on the synthesis, protonation, and coordination chemistry of chelating guanidine ligands with biphenyl, binaphthyl, and bipyridyl backbones. The ligands are shown to be proton sponges, and this protonation was studied experimentally and by using quantum-chemical calculations. Group 10 metal (Ni, Pd, and Pt) complexes with different metal/ligand ratios were synthesized. In the case of the bipyridyl systems, coordination occurs exclusively at the pyridine N atoms, as opposed to protonation. The spin-density distribution and the magnetism were evaluated for a series of paramagnetic NiII complexes with the aid of paramagnetic NMR spectroscopic studies in alliance with quantum-chemical calculations and magnetic (SQUID) measurements. Through direct delocalization from the singly occupied molecular orbitals (SOMOs), a significant amount of spin density is placed on the guanidinyl groups, and spin polarization also transports spin density onto the aromatic backbone.
Item Description:Gesehen am 23.06.2021
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201204294

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