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1997•Inorganic ChemistryRequires access

Hydrolysis of Unactivated Esters and Acetonitrile Hydration by a Hydroxo−Dicopper(II) Complex

Steven T. Frey, Narasimha N. Murthy, Susan T. Weintraub, Laurence Kenneth Thompson, Kenneth D. Karlin

Open publisher page 40 citations

Abstract

Binuclear metal−hydroxide centers are implicated in many protein hydrolases. Here, we show that the binucleating ligand N,N,N‘,N‘-tetrakis(2-pyridylmethyl)-1,3-diamino-2-propanol (L−OH) reacts with 2 equiv of CuI and O2, giving the tetranuclear complex [Cu4(L−O-)2(μ-OH-)2]4+ (1) (X-ray), established to give binuclear species 2 upon dissolution in CH3CN. Labeling experiments show that the hydroxide moiety in 2 acts as a nucleophile for the efficient hydrolysis of unactivated acetate esters, yielding the μ-acetato-bridged complexes 3. Species 2 also slowly hydrates acetonitrile, yielding the μ-amidate−dicopper(II) complex 4.

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Binuclear metal−hydroxide centers are implicated in many protein hydrolases. Here, we show that the binucleating ligand N,N,N‘,N‘-tetrakis(2-pyridylmethyl)-1,3-diamino-2-propanol (L−OH) reacts with 2 equiv of CuI and O2, giving the tetranuclear complex [Cu4(L−O-)2(μ-OH-)2]4+ (1) (X-ray), established to give binuclear species 2 upon dissolution in CH3CN. Labeling experiments show that the hydroxide moiety in 2 acts as a nucleophile for the efficient hydrolysis of unactivated acetate esters, yielding the μ-acetato-bridged complexes 3. Species 2 also slowly hydrates acetonitrile, yielding the μ-amidate−dicopper(II) complex 4.

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Available abstract

Binuclear metal−hydroxide centers are implicated in many protein hydrolases. Here, we show that the binucleating ligand N,N,N‘,N‘-tetrakis(2-pyridylmethyl)-1,3-diamino-2-propanol (L−OH) reacts with 2 equiv of CuI and O2, giving the tetranuclear complex [Cu4(L−O-)2(μ-OH-)2]4+ (1) (X-ray), established to give binuclear species 2 upon dissolution in CH3CN. Labeling experiments show that the hydroxide moiety in 2 acts as a nucleophile for the efficient hydrolysis of unactivated acetate esters, yielding the μ-acetato-bridged complexes 3. Species 2 also slowly hydrates acetonitrile, yielding the μ-amidate−dicopper(II) complex 4.

Key concepts: Chemistry, Acetonitrile, Hydrolysis, Medicinal chemistry, Organic chemistry, Polymer chemistry

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