Charge distribution in diacetylene, cyanoacetylene and ethylacetylene anions

Shmaryahu Hoz, Pinchas Aped

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Atomic charges were calculated for acetylene, diacetylene, cyanoacetylene, ethylacetylene and their conjugated bases at the 6-31G* 6-31 + G* level. Subtraction of the atomic charges of the neutral compounds from those of the anions gave the charges developed on the various atoms upon deprotonation. A significant negative charge is developed on the terminal heavy atom of diacetylene and cyanoacetylene, whereas no charge is developed on the terminal methyl group of ethylacetylene. This difference, along with the better accessibility to solvation, may account for the change from a 'normal' acid behaviour of acetylene to the pseudo acid behaviour in the conjugated acetylenes.

Original languageEnglish
Pages (from-to)275-280
Number of pages6
JournalJournal of Molecular Structure: THEOCHEM
Volume398-399
DOIs
StatePublished - 30 Jun 1997

Keywords

  • Carbon acids
  • Charge delocalization
  • Diacetylene

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