103549-15-1Relevant academic research and scientific papers
Large Transition State Imbalance in the Expulsion of Arylnitromethane Anions from Aniline Adducts of α-Nitrostilbenes
Bernasconi, Claude F.,Renfrow, Richard A.
, p. 5404 - 5413 (1994)
Aniline adducts of α-nitrostilbenes, PhCH(HNC6H4Z)CH(C6H4Y)NO2 have been synthesized for a variety of Z/Y combinations.In several cases a mixture of two diastereomers was obtained.Structural assignment of the diastereomers was based both on 1H NMR and reactivity data.The kinetics of the breakdown of the adducts into the respective benzanilines and arylnitromethane anions was studied in acidic 50percent Me2SO-50percent water solutions at 5 deg C.The rate constants, kexp, were found to be independent of buffer concentration and pH, indicating a unimolecular mechanism.There is a strong dependence on the aniline substituent (ρ = -2.2) and the pKa of the arylnitromethanes (βlg = -1.28).By estimating the substituent dependence of the equilibrium constant (Kexp), approximate normalized structure-reactivity parameters αexpn = (dlog kexp/dlog Kexp)Z ca. 1.28 and βexpn = (dlog kexp/dlog Kexp)Y ca. 0.58 have been calculated.This suggests the presence of a substantial transition state imbalance (αexpn - βexpn ca. 0.70), similar to that in the deprotonation of arylnitromethanes.
PRODUCTS FROM THE REACTION OF α-NITRO- AND α,β-DINITROSTILBENE WITH AMINES AND THEIR VIBRATIONAL SPECTRA
Todres, Z. V.,Dyusengaliev, K. I.,Garbuzova, I. A.
, p. 325 - 330 (2007/10/02)
With aniline and cyclohexylamine, cis-α-nitrostilbene forms the products from addition of the amine at the olefinic bond.In reaction with morpholine, aniline, and its N-monoalkyl derivatives cis-α,β-dinitrostilbene undergoes substitution of one nitro grou
