Accession Number : AD0692073

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

Corporate Author : NAVAL ORDNANCE LAB WHITE OAK MD

Personal Author(s) : Burlinson,Nicholas ; Kaplan,Lloyd A.

Report Date : 13 MAY 1969

Pagination or Media Count : 26

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)

Descriptors :   (*ALKENES, SOLUTIONS(MIXTURES)), (*ORGANIC NITROGEN COMPOUNDS, SOLUTIONS(MIXTURES)), THERMODYNAMICS, ESTERS, SULFOXIDES, NITRILES, REACTION KINETICS, ULTRAVIOLET SPECTRA, VISIBLE SPECTRA, IONS

Subject Categories : Atomic and Molecular Physics and Spectroscopy

Distribution Statement : APPROVED FOR PUBLIC RELEASE