Acidity of Carboxylic Acids: A Rebuttal and Redefinition-Reference-Cited by-同舟云学术

Acidity of Carboxylic Acids: A Rebuttal and Redefinition

Published:2001-09-08 Issue:39 Volume:123 Page:9564-9570
ISSN:0002-7863
Container-title:Journal of the American Chemical Society
language:en
Short-container-title:J. Am. Chem. Soc.

Author:

Exner Otto¹,Čársky Petr¹

Affiliation:

1. Contribution from the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 16610 Praha 6, Czech Republic, and the J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, 18223 Praha 8, Czech Republic

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Link

https://pubs.acs.org/doi/pdf/10.1021/ja003665%2B

Reference41 articles.

1. For instance: (a) March, J.Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; p 264. (b) Solomons, T. W. G.Organic Chemistry, 5th ed.; John Wiley and Sons: New York, 1992, Chapter 3.5B. (c) Carey, F. A.Organic Chemistry, 3rd ed.; McGraw-Hill: New York, 1996; p 770−771. (d) Walter, W.Beyer-Walter Lehrbuch der Organischen Chemie, 22nd ed.; S. Hinzel Verlag: Stuttgart, 1991; p 233−234. Ref 1a,b report also the alternative theory.

2. Why are organic acids stronger acids than organic alcohols?

3. Valency correlation diagrams

4. Isodesmic reaction energies and the relative acidities of carboxylic acids and alcohols

5. Resonance delocalization in the anion is not the major factor responsible for the higher acidity of carboxylic acids relative to alcohols

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