Solvent Effects in Nucleophilic Substitution Reaction

Determination of pKa’s of hydroxamic acids by nucleophilic substitution reaction

Acid dissociation constant (pKa) of some para-substituted benzohydroxamic, 4-XC6H4CONHOH, and N-methyl parasubstituted benzohydroxamic acids, 4XC6H4CON(OH)CH3, where X = H, CH3, CH3O, NO2, Cl, have been determined spectrophotometrically by nucleophilic substitution reactions of pnitrophenyl acetate with hydroxamate ions at 27± 0.1C. All reactions in this study follow pseudo-first order kinetics...

Dynamic origin of the stereoselectivity of a nucleophilic substitution reaction.

A nucleophilic substitution on a dichlorovinyl ketone was studied experimentally and computationally. A mixture of products is observed experimentally, but a conventional computational analysis does not account for the formation of the minor stereoisomer. Instead, the product mixture is predicted accurately from a dynamic trajectory study on a bifurcating energy surface. The dynamic origin of t...

Nucleophilic Substitution and Elimination

What does the term "nucleophilic substitution" imply? • A nucleophile is an the electron rich species that will react with an electron poor species • A substitution implies that one group replaces another. Nucleophilic substitution reactions occur when an electron rich species, the nucleophile, reacts at an electrophilic saturated C atom attached to an electronegative group (important), the lea...

Modern Nucleophilic Aromatic Substitution

Gas phase nucleophilic substitution

The literature on gas phase nucleophilic substitution reactions at aliphatic carbon has been reviewed. The emphasis has been on journal articles published in the period 1990–2001. The present review outlines our current understanding of concepts such as potential energy surfaces, structure–energy relationships, microsolvation, and dynamical and mechanistic details based on both experimental and...