Synthesis of the Bifunctional Ambiphilic Molecule 2-(picolyl) trimethylstannane and Study of its Hydrolysis Kinetics Using Hydrogen NMR .

摘要

The ambiphilic bifunctional molecule 2-(picolyl)trimethylstannane ( A) was synthesized in the reaction between 2-(picolyl)lithium and trimethyltinchloride. The product was characterized with 1H and 13C NMR. The molecule was found to hydrolyze spontaneously in air. The hydrolysis mechanism likely involves hydrogen bonding of water to the nitrogen atom, significant polarization and buildup of electron density on the oxygen atom of water, and nucleophilic attack on the tin atom. We propose a rate law ( rate = k[A][H2O]) consistent with the hypothesized mechanism, and attempt to measure the hydrolysis kinetics with NMR spectroscopy. The occurrence of hydrolysis reaction is only possible due to the proximity of the Lewis centers on the bifunctional ambiphilic molecule.