Does a Methyl Substituent Stabilize or Destabilize Anions?

Addy Pross, Leo Radom

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

Ab initio molecular orbital calculations show that whereas methanol is a stronger acid than water, propyne is a weaker acid than acetylene, and acetic acid is a weaker acid than formic acid, in agreement with gas-phase experimental data. A rationalization for this capability of a methyl substituent to sometimes stabilize and sometimes destabilize anions relative to their parent acids is provided within the framework of perturbation molecular orbital theory.

Original languageEnglish
Pages (from-to)6572-6575
Number of pages4
JournalJournal of the American Chemical Society
Volume100
Issue number21
DOIs
StatePublished - 1 Jan 1978
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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