PLANAR DINITRO CARBANIONS: CORRELATION OF THERMODYNAMIC CARBON ACIDITY WITH SIGMA SUB R(-),

Abstract

The pKa values for a series 2-Y-vinyldinitromethanes (where Y = COOCH3, CN, SO2CH3, and NO2) were determined in methanol at 15C. The strong acidity of these carbon acids indicates that the negative charge on the conjugate base, 2-Y-vinyldinitromethide ion is completely delocalized over the three conjugating groups. A plot of log Ka vs the function (sigma(I) + sigma(R)(-)) for the Y substituent gave excellent linear correlation. This suggests that these carbanions are completely coplanar in solution. (Author)

Document Details

Document Type
Technical Report
Publication Date
May 13, 1969
Accession Number
AD0692073

Entities

People

  • Lloyd A. Kaplan
  • Nicholas Burlinson

Organizations

  • Naval Ordnance Laboratory

Tags

DTIC Thesaurus Topics

  • Alcohols
  • Chemical Compounds
  • Methanols

Fields of Study

  • Chemistry

Readers

  • Analytical Mechanics
  • Materials Science and Engineering.
  • Organic Chemistry