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THE BASICITIES OF ORTHO-SUBSTITUTED BENZOIC ACIDS

 

作者: Ross Stewart,   Maurice R. Granger,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1961)
卷期: Volume 39, issue 12  

页码: 2508-2515

 

ISSN:0008-4042

 

年代: 1961

 

DOI:10.1139/v61-331

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

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.

 

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