Selective Lability of Ruthenium(II) Arene Amino Acid Complexes

Selective Lability of Ruthenium(II) Arene Amino Acid Complexes

A series of organometallic complexes of the form [(PhH)­Ru­(amino acid)]+ have been synthesized using amino acids able to act as tridentate ligands. The straightforward syntheses gave enantiomerically pure complexes with two stereogenic centers due to the enantiopurity of the chelating ligands. Comp...

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Bibliographic Details
Published in:Inorganic chemistry Vol. 54; no. 7; pp. 3118 - 3124
Main Authors: Scrase, Tom G, O’Neill, Michael J, Peel, Andrew J, Senior, Paul W, Matthews, Peter D, Shi, Heyao, Boss, Sally R, Barker, Paul D
Format: Journal Article
Language:English
Published: United States American Chemical Society 06-04-2015
Subjects:
Amino acids
Amino Acids - chemistry
Aromatic compounds
Benzene - chemistry
Exchange
Ligands
Links
Metalorganic compounds
Molecular Structure
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Residues
Ruthenium - chemistry
Stability
Stereoisomerism
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Summary:A series of organometallic complexes of the form [(PhH)­Ru­(amino acid)]+ have been synthesized using amino acids able to act as tridentate ligands. The straightforward syntheses gave enantiomerically pure complexes with two stereogenic centers due to the enantiopurity of the chelating ligands. Complexes were characterized in the solid-state and/or solution-state where the stability of the complex allowed. The propensity toward labilization of the coordinatively saturated complexes was investigated. The links between complex stability and structural features are very subtle. Nonetheless, H/D exchange rates of coordinated amino groups reveal more significant differences in reactivity linked to metallocycle ring size resulting in decreasing stability of the metallocycle as the amino acid side-chain length increases. The behavior of these systems in acid is unusual, apparently labilizing the carboxylate residue of the amino acid. This acid-catalyzed hemilability in an organometallic is relevant to the use of Ru­(II) arenes in medicinal contexts due to the relatively low pH of cancerous cells.
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ISSN:0020-1669
1520-510X
DOI:10.1021/ic502051y