• carbon(0);
  • carbon(II);
  • gem-dimetallation;
  • nucleophile;
  • electrophile

Quantum chemical calculations are performed on different carbon bases to understand the origin of their reactivity. Both carbon(0) and carbon(II) bases may show very high values of second proton affinity as well as bond dissociation energies for gem-dimetallation. Thus, their distinction becomes blurred when subjected to electrophilic attack. However, unlike carbon(0) bases, carbon(II) bases are ambiphilic in nature owing to the presence of a σ symmetric lone pair and a vacant π orbital concentrated on the central carbon atom. Thus, they may show different reactivity when subjected to nucleophilic attack. This reactivity difference may be considered as another distinction between these two classes of compounds. © 2013 Wiley Periodicals, Inc.