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Synthesis and Structure of a Novel Substituted Benzothiazolyl-N-phenyl-2-pyridinecarbothioamide; Kinetics of Formation and Electrochemistry of Two of its Palladium Pincer Complexes

Journal article
Authors M. A. W. Lawrence
Y. A. Jackson
W. H. Mulder
Per Martin Björemark
Mikael Håkansson
Published in Australian Journal of Chemistry
Volume 68
Issue 5
Pages 731-741
ISSN 0004-9425
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 731-741
Language en
Links dx.doi.org/10.1071/ch14380
Keywords TEMPERATURE SUZUKI-MIYAURA, ANTITUMOR BENZOTHIAZOLES, IN-VITRO, RUTHENIUM COMPLEXES, MOLECULAR-STRUCTURE, CROSS-COUPLINGS, THIOAMIDE, UNITS, CATALYST, LIGANDS, 2-(4-AMINOPHENYL)BENZOTHIAZOLES, Chemistry, Multidisciplinary, EPHENS FF, 1950, JOURNAL OF THE CHEMICAL SOCIETY, P3336, EVENS MFG, 1994, JOURNAL OF MEDICINAL CHEMISTRY, V37, P1689
Subject categories Chemical Sciences

Abstract

The synthesis and crystal structures of bis-N-(2,5-dimethoxyphenyl)pyridine-2,6-dicarbothioamide (dicarbothioamide I) and 6-(4,7-dimethoxy-2-benzothiazolyl)-N-(2,5-dimethoxyphenyl)-2-pyridinecar bothioamide (L-1) as well as the syntheses of the palladium(ii) chloride and acetate pincer complexes are reported. The stability constant for the palladium complex formation at 25 degrees C was found to be (2.04 +/- 0.26)x10(4)dm(3)mol(-1) and (2.30 +/- 0.19)x10(4)dm(3)mol(-1) with H-f=8 +/- 1kJmol(-1), S-f=108 +/- 10JK(-1)mol(-1), and H-f=17 +/- 4kJmol(-1) and S-f=140 +/- 20JK(-1)mol(-1) for the PdClL1 and Pd(OAc)L-1, respectively. The kinetics of formation of the palladium(ii) complexes were investigated and the mechanism is proposed to be associative in nature (H-1(double dagger)=34 +/- 2kJmol(-1) and S-1(double dagger)=-113 +/- 8JK(-1)mol(-1), and H-1(double dagger)=37 +/- 3kJmol(-1) and S-1(double dagger)=-100 +/- 8JK(-1)mol(-1) for the PdClL1 and Pd(OAc)L-1 species, respectively). The electrochemical measurements of the acetonitrile solutions revealed irreversible electron transfers consistent with the electrochemical decomposition of the ligand and its coordination complexes.

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