In this follow-up to the previous post, I will try to address the question what is the nature of the bonds in penta-coordinate carbon?
Posts Tagged ‘Hypervalency’
Capturing penta-coordinate carbon! (Part 2).
Wednesday, September 23rd, 2009Capturing penta-coordinate carbon! (Part 1).
Tuesday, September 22nd, 2009The bimolecular nucleophilic substitution reaction at saturated carbon is an icon of organic chemistry, and is better known by its mechanistic label, SN2. It is normally a slow reaction, with half lives often measured in hours. This implies a significant barrier to reaction (~15-20 kcal/mol) for the transition state, shown below (X is normally both a good nucleophile and a good nucleofuge/leaving group, such as halide, cyanide, etc. Y can have a wide variety of forms).