91289-36-0Relevant academic research and scientific papers
Compositions derived from quinoline and quinoxaline, preparation and use thereof
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Page/Page column 38, (2008/06/13)
The present invention concerns compounds derived from quinoline and quinoxaline, their preparation and their uses, particularly in the field of therapeutics and vaccines or for developing active compounds. The inventive compounds are of general formula (I
The Metal-ion-promoted Water- and Hydroxide-ion-catalysed Hydrolysis of Amides
Przystas, Theodore J.,Fife, Thomas H.
, p. 393 - 399 (2007/10/02)
Rate constants have been determined for the hydrolysis of 8-trifluoroacetamidoquinoline-2-carboxylic acid and N-(6-carboxypicolinyl)-2,4-dinitroaniline in water at 70 deg C.The hydrolysis reactions of these amides in the absence of metal ions are OH- catalysed at pH values >7.Divalent metal ions (Co2+, Ni2+, and Zn2+) have a significant catalytic effect on the rates of hydrolysis.Binding of the metal ions to the amides is strong, and saturation occurs at low metal ion concentrations (-1).At saturating concentrations of the metal ions kobs ispH independent at pH- catalysed reactions are not observed.In contrast, the Ni2+ catalysed hydrolysis of the β-lactam, N-(8-quinolyl)azetidin-2-one, proceeds through a metal-ion-promoted OH- reaction.A 0.01 mol dm-1 concentration of Ni2+ (non saturating) provides a rate enhancement of 105 over that observed in the absence of metal ion.The tye of metal ion catalysis observed in amide hydrolysis, i.e., pH independent or OH- dependent, must be determined by the nature of the rate-determining step and the ease of C-N bond breaking.A metal-ion-promoted OH- catalysed reaction will occur att pH values near neutrality when C-N bond breakng is facile and nucleophilic attack is rate determining, whereas when C-N bond breaking is difficult, and therefore part of the rate-determing step, the reaction will be pH independent because of the requirement for protonation of the nitrogen leaving group.
