Structural sources of chiral discrimination in diastereoisomeric Ru(II) complexes of aromatic aminoacids and diimines

Paul Emseis; Peter Leverett; Peter A. Williams; Ray J. Butcher

Structural sources of chiral discrimination in diastereoisomeric Ru(II) complexes of aromatic aminoacids and diimines

Paul Emseis, Peter Leverett, Peter A. Williams, Ray J. Butcher

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3 Citations (Scopus)

Abstract

The single-crystal structure of a previously reported Ru(II) complex salt, ÃƒÅ½Ã¢â‚¬Â-[Ru(bpy)2(S-tyr)]ClO4 ÃƒÆ’Ã¢â‚¬Å¡Ãƒ"šÃ‚Â· benzene (bpy = 2,2ÃƒÂ¢Ã¢"šÂ¬Ã‚Â²-bipyridyl; tyr = tyrosinato) has been refined in its correct setting. The salt contains the cation that is thermodynamically unstable in aqueous solution at 298 K with respect to the ÃƒÅ½Ã¢â‚¬Âº diastereoisomer. Its stability in the solid state is ascribed to the influence of intramolecular NHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ and CHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ interactions involving the aromatic ring of the aminoacidate with the amine group and a pyridyl ring of one of the diimine ligands. The benzene of crystallization is involved with similar CHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬, ÃƒÂÃ¢"šÂ¬ÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ and ÃƒÂÃ¢"šÂ¬-facial interactions with the bpy and tyrosinato ligands, and this too may serve to stabilize the particular diastereoisomer in the lattice.

Original language	English
Number of pages	4
Journal	Inorganica Chimica Acta
Publication status	Published - 2004

Keywords

Ruthenium compounds
amino acids
aromatic compounds
chirality
crystallization
diastereoisomers

Cite this

@article{5a32e5a662164724840739577f78cd21,

title = "Structural sources of chiral discrimination in diastereoisomeric Ru(II) complexes of aromatic aminoacids and diimines",

abstract = "The single-crystal structure of a previously reported Ru(II) complex salt, {\~A}ƒ{\AA}½{\~A}¢{\^a}‚¬{\^A}-[Ru(bpy)2(S-tyr)]ClO4 {\~A}ƒ{\AE}{\textquoteright}{\~A}¢{\^a}‚¬{\AA}¡{\~A}ƒ{"}{\v s}{\~A}‚{\^A}· benzene (bpy = 2,2{\~A}ƒ{\^A}¢{\~A}¢{"}{\v s}{\^A}¬{\~A}‚{\^A}²-bipyridyl; tyr = tyrosinato) has been refined in its correct setting. The salt contains the cation that is thermodynamically unstable in aqueous solution at 298 K with respect to the {\~A}ƒ{\AA}½{\~A}¢{\^a}‚¬{\^A}º diastereoisomer. Its stability in the solid state is ascribed to the influence of intramolecular NH{\~A}ƒ{\^A}¢{\~A}¢{"}{\v s}{\^A}¬{\~A}¢{\^a}‚¬{\AA}“{\~A}ƒ{\^A}{\~A}¢{"}{\v s}{\^A}¬ and CH{\~A}ƒ{\^A}¢{\~A}¢{"}{\v s}{\^A}¬{\~A}¢{\^a}‚¬{\AA}“{\~A}ƒ{\^A}{\~A}¢{"}{\v s}{\^A}¬ interactions involving the aromatic ring of the aminoacidate with the amine group and a pyridyl ring of one of the diimine ligands. The benzene of crystallization is involved with similar CH{\~A}ƒ{\^A}¢{\~A}¢{"}{\v s}{\^A}¬{\~A}¢{\^a}‚¬{\AA}“{\~A}ƒ{\^A}{\~A}¢{"}{\v s}{\^A}¬, {\~A}ƒ{\^A}{\~A}¢{"}{\v s}{\^A}¬{\~A}ƒ{\^A}¢{\~A}¢{"}{\v s}{\^A}¬{\~A}¢{\^a}‚¬{\AA}“{\~A}ƒ{\^A}{\~A}¢{"}{\v s}{\^A}¬ and {\~A}ƒ{\^A}{\~A}¢{"}{\v s}{\^A}¬-facial interactions with the bpy and tyrosinato ligands, and this too may serve to stabilize the particular diastereoisomer in the lattice.",

keywords = "Ruthenium compounds, amino acids, aromatic compounds, chirality, crystallization, diastereoisomers",

author = "Paul Emseis and Peter Leverett and Williams, {Peter A.} and Butcher, {Ray J.}",

year = "2004",

language = "English",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier",

}

TY - JOUR

T1 - Structural sources of chiral discrimination in diastereoisomeric Ru(II) complexes of aromatic aminoacids and diimines

AU - Emseis, Paul

AU - Leverett, Peter

AU - Williams, Peter A.

AU - Butcher, Ray J.

PY - 2004

Y1 - 2004

N2 - The single-crystal structure of a previously reported Ru(II) complex salt, ÃƒÅ½Ã¢â‚¬Â-[Ru(bpy)2(S-tyr)]ClO4 ÃƒÆ’Ã¢â‚¬Å¡Ãƒ"šÃ‚Â· benzene (bpy = 2,2ÃƒÂ¢Ã¢"šÂ¬Ã‚Â²-bipyridyl; tyr = tyrosinato) has been refined in its correct setting. The salt contains the cation that is thermodynamically unstable in aqueous solution at 298 K with respect to the ÃƒÅ½Ã¢â‚¬Âº diastereoisomer. Its stability in the solid state is ascribed to the influence of intramolecular NHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ and CHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ interactions involving the aromatic ring of the aminoacidate with the amine group and a pyridyl ring of one of the diimine ligands. The benzene of crystallization is involved with similar CHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬, ÃƒÂÃ¢"šÂ¬ÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ and ÃƒÂÃ¢"šÂ¬-facial interactions with the bpy and tyrosinato ligands, and this too may serve to stabilize the particular diastereoisomer in the lattice.

AB - The single-crystal structure of a previously reported Ru(II) complex salt, ÃƒÅ½Ã¢â‚¬Â-[Ru(bpy)2(S-tyr)]ClO4 ÃƒÆ’Ã¢â‚¬Å¡Ãƒ"šÃ‚Â· benzene (bpy = 2,2ÃƒÂ¢Ã¢"šÂ¬Ã‚Â²-bipyridyl; tyr = tyrosinato) has been refined in its correct setting. The salt contains the cation that is thermodynamically unstable in aqueous solution at 298 K with respect to the ÃƒÅ½Ã¢â‚¬Âº diastereoisomer. Its stability in the solid state is ascribed to the influence of intramolecular NHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ and CHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ interactions involving the aromatic ring of the aminoacidate with the amine group and a pyridyl ring of one of the diimine ligands. The benzene of crystallization is involved with similar CHÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬, ÃƒÂÃ¢"šÂ¬ÃƒÂ¢Ã¢"šÂ¬Ã¢â‚¬Å“ÃƒÂÃ¢"šÂ¬ and ÃƒÂÃ¢"šÂ¬-facial interactions with the bpy and tyrosinato ligands, and this too may serve to stabilize the particular diastereoisomer in the lattice.

KW - Ruthenium compounds

KW - amino acids

KW - aromatic compounds

KW - chirality

KW - crystallization

KW - diastereoisomers

UR - http://handle.uws.edu.au:8081/1959.7/10688

M3 - Article

SN - 0020-1693

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

ER -

Structural sources of chiral discrimination in diastereoisomeric Ru(II) complexes of aromatic aminoacids and diimines

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