THE BASICITIES OF ORTHO-SUBSTITUTED BENZOIC ACIDS
- 1 December 1961
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 39 (12) , 2508-2515
- https://doi.org/10.1139/v61-331
Abstract
The basicities of 15 ortho-substituted benzoic acids have been measured in sulphuric acid. The ortho effects of alkyl groups are base weakening and increase in the expected order methyl, ethyl, i-propyl, t-butyl. Ortho halo benzoic acids have comparable basicities and are weaker than their para isomers. Oxygen-containing ortho substituents, except hydroxyl, all cause substantial base strengthening relative to the para isomers. Even the groups nitro and carboxyl when substituted ortho in benzoic acid cause the basicity to rise, presumably because of hydrogen bonding in the conjugate acids.Keywords
This publication has 9 references indexed in Scilit:
- Stereoelectronic Effects on Organic Bases. II.1 Base Strengths of the Phenolic Ethers2Journal of the American Chemical Society, 1960
- The Position of Protonation of the Carboxyl Group1Journal of the American Chemical Society, 1960
- Carbonium Ions. VIII. Diarylolefin-Diarylalkyl Cation Equilibria1Journal of the American Chemical Society, 1959
- A Quantitative Approach to the Ortho Effects of Halogen Substituents in Aromatic Systems1,2Journal of the American Chemical Society, 1955
- Basic Dissociation Constants of Some Substituted Flavones1Journal of the American Chemical Society, 1954
- The Kinetics of the Base-catalyzed Methanolysis of Ortho, Meta and Para Substituted l-Menthyl Benzoates1,2Journal of the American Chemical Society, 1950
- Mesomerism and OrientationNature, 1939
- The Determination of Ionization by Ultraviolet Spectrophotometry: Its Validity and its Application to the Measurement of the Strength of Very Weak Bases1Journal of the American Chemical Society, 1935
- The Anomalous Strength of Salicylic AcidJournal of the American Chemical Society, 1934