ACIDITY OF CARBOXYLIC-ACIDS - RESONANCE DELOCALIZATION OR INDUCTION

Authors
Citation
Td. Thomas, ACIDITY OF CARBOXYLIC-ACIDS - RESONANCE DELOCALIZATION OR INDUCTION, Perkin transactions. 2, (9), 1994, pp. 1945-1948
Citations number
14
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
ISSN journal
03009580
Issue
9
Year of publication
1994
Pages
1945 - 1948
Database
ISI
SICI code
0300-9580(1994):9<1945:AOC-RD>2.0.ZU;2-V
Abstract
On the basis of calculated acidities of the vinylogues of formic acid and vinyl alcohol, Dewar and Krull have concluded that the higher acid ity of carboxylic acids relative to alcohols is due to stabilization o f the conjugate anion by resonance delocalization. More detailed calcu lations on some of the compounds that they have considered shows indee d that delocalization of charge in the anion plays a role in the acidi ty of buta-1,3-dien-1-ol 1 relative to vinyl alcohol and of 3-hydroxyp rop-2-enal 2 relative to formic acid. However, these calculations show that this conclusion is not applicable to the relative acidities of e thanol, vinyl alcohol and formic acid or of 2 relative to 1.These are due to the charge distribution in the neutral molecule, in keeping wit h the ideas proposed by Siggel et al.