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The inductive effect does not explain electron density in haloacetates: are our textbooks wrong?

Edwin C Johnson1,2, Kasimir P Gregory2,3,4,5, Hayden Robertson2,6

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The inductive effect does not explain acidity trends in haloacetic acids. Wave functional theory and experimental data reveal substituent electronegativity is inversely related to carboxylate charge density, challenging established chemical principles.

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Area of Science:

  • Physical Chemistry
  • Organic Chemistry

Background:

  • The inductive effect is a fundamental concept explaining acidity trends in carboxylic acids.
  • Acidity is typically correlated with electron density reduction at the carboxylate group via inductive effects.

Purpose of the Study:

  • To investigate the role of the inductive effect in determining the pKa values of acetic acid derivatives.
  • To challenge the conventional explanation of acidity trends based on substituent electronegativity.

Main Methods:

  • Wave functional theory calculations were performed on trihaloacetate derivatives.
  • Experimental validation included gas phase acidities, polymer solubility studies (poly(N-isopropylacrylamide)), and 13C NMR spectroscopy of haloalkanes.

Main Results:

  • Wave functional theory revealed that charge density is inversely related to substituent electronegativity, contrary to the inductive effect.
  • Experimental data, including polymer solubility and NMR spectroscopy, supported these unexpected findings.
  • The trichloroacetate group showed the greatest reduction in carboxylate oxygen charge density.

Conclusions:

  • The inductive effect does not accurately explain the observed pKa trends in haloacetic acids.
  • Substituent effects on charge density are more complex than previously understood and are not solely governed by electronegativity.
  • This study necessitates a re-evaluation of fundamental chemical principles related to substituent effects.