Related Experiment Video
Updated: Jul 27, 2025

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
Published on: August 19, 2013
Structure-property relationships of fluorinated carboxylic acid bioisosteres
Thibault Alle1, Sipak Joyasawal2, Killian Oukoloff1
1Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, United States.
Abstract:
Fluorinated alcohols and phenols are potentially useful as bioisosteres of the carboxylic acid functional group. To enable a direct comparison of the properties of fluorinated carboxylic acid surrogates with those of other commonly used, non-fluorinated bioisosteres, we conducted a structure-property relationship (SPR) study based on matched molecular pair (MMP) analyses. A series of representative examples have been characterized by experimentally determining physicochemical properties, such as acidity (pKa), lipophilicity (logD7.4), and permeability (PAMPA). The results presented can help estimate the relative changes in physicochemical properties that may be attainable by replacing the carboxylic acid functional group with fluorine containing surrogate structures.
More Related Videos
Related Concept Videos
Physical Properties of Carboxylic Acid Derivatives
Among the carboxylic acid derivatives, the boiling points of acid chlorides and esters are very similar and are the lowest in the series. Acid anhydrides have slightly higher boiling...
Physical Properties of Carboxylic Acids
Substituent Effects on Acidity of Carboxylic Acids
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Carboxylic Acid Derivatives: Overview

