153788-45-5Relevant articles and documents
Equilibrium acidities of some α,ω-diphenylpolyenes
Thiele, Georg,Streitwieser, Andrew
, p. 446 - 454 (2007/10/02)
Cesium ion pair acidities were measured in THF for a series of diphenylmethane vinylogues that form α,ω-diphenylpolyenyl anions with linearly conjugated chains of 3-9 carbon atoms. The dissociation constants of the diphenylpolyenyls in THF were determined by UV-vis spectroscopy and are rationalized with an electrostatic model. Acidity and dissociation data were combined with measurements of stereoisomer equilibria to estimate the differences in delocalization energy among the diphenylpolyenyl ions. The experimental differences in acidity correlate well with AMI and molecular mechanics (MMPI) calculations.