Ortho-substituted Benzoic Acids Research Articles

Hydrogen Bonding and the ortho Effect in Acetonitrile. Reaction of ortho-Substituted Benzoic Acids with Amines

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTHydrogen Bonding and the ortho Effect in Acetonitrile. Reaction of ortho-Substituted Benzoic Acids with AminesJ. F. Coetzee and G. P. CunninghamCite this: J. Am. Chem. Soc. 1965, 87, 12, 2534–2539Publication Date (Print):June 1, 1965Publication History Published online1 May 2002Published inissue 1 June 1965https://doi.org/10.1021/ja01090a002RIGHTS & PERMISSIONSArticle Views186Altmetric-Citations15LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (633 KB) Get e-Alerts Get e-Alerts

345. The separation of polar and steric effects. Part I. The kinetics of the reaction of ortho-substituted benzoic acids with diazodiphenylmethane

345. The separation of polar and steric effects. Part I. The kinetics of the reaction of ortho-substituted benzoic acids with diazodiphenylmethane

THE BASICITIES OF ORTHO-SUBSTITUTED BENZOIC ACIDS

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.