The stabilities of Meisenheimer complexes. Part 39. Steric effects on rate and equilibrium constants for σ-adduct formation from alkyl 2,4,6-trinitro-phenyl ethers and ethoxide ions in ethanol
Abstract
Rate and equilibrium data are reported for reactions of ethoxide ions in ethanol with four alkyl 2,4,6-trinitrophenyl ethers to give isomeric 1,3 and 1,1 σ-adducts. The results indicate the importance of steric factors in this series. Increasing the size of the alkyl substituent causes decreases in values of k3, the rate coefficient, and K3, the equilibrium constant, for reaction at the unsubstituted 3-position, and also causes decreases in values of k1 for reaction at the substituted position.