X-RAY STRUCTURE OF AN AMIDE-APPENDED CHLOROMERCURATED DERIVATIVE OF 2-PHENYLQUINOLINE

synthesis mercury complexes orthometallation reactions crystal structure.

КВАНТОВО-ХИМИЧЕСКИЙ АНАЛИЗ МОЛЕКУЛЯРНОЙ СТРУКТУРЫ И КОЛЕБАТЕЛЬНОГО СПЕКТРА АРГЛАБИНА, TWO ISOMERIC STRUCTURES OF OXOVANADIUM(V) COMPLEXES WITH HYDRAZONE AND 8-HYDROXYQUINOLINE LIGANDS, ...

2015. 56, 5 - - – - UDC 541.6:547.13:546.49 X-RAY STRUCTURE OF AN AMIDE-APPENDED CHLOROMERCURATED DERIVATIVE OF 2-PHENYLQUINOLINE C.-Y. Lin, W. Henderson, B.K. Nicholson Department of Chemistry, School of Science, University of Waikato, Hamilton, New Zealand E-mail: w.henderson@waikato.ac.nz Received February, 03, 2014 Reaction of the morpholine amide derivative of 2-phenyl-4-quinolinecarboxylic acid with mercury(II) acetate and lithium chloride results in chloromercuration at the ortho position on the phenyl ring; the complex was characterised by ESI mass spectrometry and an X-ray structure determination. <...> INTRODUCTION Organomercury compounds have found to be versatile reagents for the synthesis of a wide range of cycloaurated gold(III) complexes through transmetallation reactions [ 1 ]. <...> The transmetallation synthesis of cycloaurated gold complexes has been applied to a wide range of systems, including substituted pyridines, azobenzenes, oxazolines, and N,N-dimethylbenzylamines among others [ 1, 2 ]. <...> One of the precursors that has been orthomercurated and converted to a cycloaurated gold complex is the methyl ester of 2-phenyl-4-quinolinecarboxylic acid 1 [ 3 ]. <...> This is significant because some cycloaurated gold(III) complexes can have relatively poor solubilities in common solvents. <...> To date, only the methyl ester of 2-phenyl-4-quinolinecarboxylic acid has been converted (via orthomercurated precursor 2) into cycloaurated gold(III) complex 3. <...> In this paper, the feasibility of orthomercurating amide derivatives is exemplified by the synthesis and structural characterization of a mercurated morpholine derivative of 2-phenyl-4-quinolinecarboxylic acid 1. <...> Elemental microanalyses were from the Campbell Microanalytical Laboratory, University of Otago. 2-Phenyl-4-quinolinecarboxylic acid (Aldrich), mercury(II) acetate (BDH), lithium chloride (BDH), morpholine (Aldrich), and thionyl chloride (Riedel de Hдen) were used as supplied. <...> The following reaction was carried out using a Schlenk line with a supply of dry nitrogen gas. 2-Phenyl-4-quinolinecarboxylic acid 1a (3.28 g, 13.2 mmol) was refluxed in thionyl chloride (5 ml, excess) for 1 h. <...> The mixture was stirred for 5 days, giving a milky white solution, which was then evaporated to dryness in the air; subsequent operations were carried out in the air. <...> The product was crystallized from a hot ethanol-water mixture (70:30), with excess sodium chloride added to aggregate the milky <...>

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