The transmission of polar effects. Part IX. The ionization and esterification with diazodiphenylmethane of 9-substituted 10-triptoic acids

descriptionPublicationkeyboard_double_arrow_right Article 15 Jan 1969 English Publisher:Canadian Science PublishingJournal:Canadian Journal of Chemistry, volume 47, pages 177-183 (issn: 0008-4042, eissn: 1480-3291,

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Authors: Keith Bowden; D. C. Parkin;

doi: 10.1139/v69-024

The transmission of polar effects. Part IX. The ionization and esterification with diazodiphenylmethane of 9-substituted 10-triptoic acids

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Abstract

A series of 9-substituted 10-triptoic acids have been prepared. Their pKa values in 80% 2-methoxy-ethanol–water and 50% ethanol–water at 25° and rate coefficients for esterification with diazodiphenyl-methane in five alcohols at 30° have been measured. The results have been analyzed by linear free energy relations. The π-inductive effect is shown to be unimportant in such systems, while the field effect model can account for the transmission.

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