Substituents on the aromatic ring systematically alter the acidity of benzoic acid derivatives
Substituents on aromatic rings systematically modulate the electronic properties and acidity of benzoic acid derivatives, a relationship reliably tracked by Hammett parameters.
The claim is a well-established chemical principle regarding Hammett substituent effects on the acidity of benzoic acid derivatives. Papers [0] and [4] specifically address benzoic acids and related carboxylic acids, showing that substituents systematically alter acidity and electronic descriptors.
Tomoko Sotomatsu, Yoshiyuki Murata, Toshio Fujita. Correlation analysis of substituent effects on the acidity of benzoic acids by the AM1 method. 1989. https://doi.org/10.1002/jcc.540100109
Paper [0] demonstrates through computational analysis that substituent effects systematically alter the electronic properties and gas-phase acidity of benzoic acid derivatives in correlation with Hammett constants.
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Alturaifi TM, Scofield GE, Wang S, Liu P. A database of steric and electronic properties of heteroaryl substituents.. 2025. https://doi.org/10.1038/s41597-025-05198-z
Paper [4] establishes Hammett-type heteroaryl substituent constants based on computed heteroaryl carboxylic acid pKa values, confirming the systematic impact of ring substituents on acidity.
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