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Issue 19, 2015
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Decarboxylation and simultaneous reduction of silver(I) β-ketocarboxylates with three types of coordinations

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Abstract

A series of silver(I) β-ketocarboxylates were prepared by reaction of β-ketocarboxylic acids with silver nitrate in the presence of diethanolamine. The silver(I) β-ketocarboxylates decomposed over a narrow temperature range to form metallic silver, CO2, and the corresponding ketones. In addition, products derived from radical intermediates were detected by mass spectroscopic analysis for some silver(I) β-ketocarboxylates. Infrared and solid state 13C-NMR spectra of silver(I) β-ketocarboxylates suggested the presence of two types of structures involving a carbonyl group in addition to the dimeric eight-membered ring structure as in the structure of silver(I) stearate. The silver(I) β-ketocarboxylate model compound used was HCOCH2COOAg and its structures were determined using density functional theory (DFT) and atoms-in-molecules (AIM) methods. Three types of coordinations around the Ag ion differing significantly in Ag–O bond strengths were found. Based on the calculated structures and experimental results, the relationships between the structures and decomposition temperatures are discussed in terms of the thermal decomposition process.

Graphical abstract: Decarboxylation and simultaneous reduction of silver(i) β-ketocarboxylates with three types of coordinations

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Publication details

The article was received on 23 Feb 2015, accepted on 01 Apr 2015 and first published on 02 Apr 2015


Article type: Paper
DOI: 10.1039/C5DT00773A
Author version available: Download Author version (PDF)
Citation: Dalton Trans., 2015,44, 8993-9003
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    Decarboxylation and simultaneous reduction of silver(I) β-ketocarboxylates with three types of coordinations

    M. Hatamura, S. Yamaguchi, S. Takane, Y. Chen and K. Suganuma, Dalton Trans., 2015, 44, 8993
    DOI: 10.1039/C5DT00773A

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