RESONANCE INTERACTIONS OF METHYLSULFONYL, METHYLTHIO AND RELATED GROUPINGS AS REVEALED BY HAMMETT SIGMA CONSTANTS

Abstract

The relative acidities of 8 m- and p-substituted thiophenols were obtained to determine the conjugative ability of the MeSO2 was significantly larger than that from BzOH, but smaller than that from phenols or anilines. This indicated the possibility of varying degrees of resonance interactions (involving an expansion of the s valence shell to 10 electrons). The data also indicated that other groups which are capable of strong resonance interactions (e.g., p-NO2, p-OMe) may exhibit more than 1 sigma value, depending on the reactions involved. (Prepared for publication in th J. Am. Chem. Soc.).

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1953
Accession Number
AD0010120

Entities

People

  • F.g. Bordwell
  • Harry M. Andersen

Organizations

  • Northwestern University

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DTIC Thesaurus Topics

  • Absorption Spectra
  • Acids
  • Aluminum Hydride
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Chloroform
  • Electrons
  • Equations
  • Hydrochloric Acid
  • Hydroxides
  • Materials
  • Organic Chemistry
  • Oxidation
  • Physical Properties
  • Sodium
  • Sodium Hydroxide

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  • Organic Chemistry
  • Quantum Chemistry

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  • Microelectronics