Abstract
High-level Density Functional Theory calculations, coupled with appropriate isodesmic reaction, are employed to investigate the effects of α-carbon, ammonium, phosphorus, and sulfur ylides, cyclization, and unsaturation on the stability, multiplicity, and reactivity of novel singlet (S) and triplet (T) carbenes. Among them the highly π-donating α-ammonium ylide is found to exert the highest stabilizing effect on the carbenic center. α-Ammonium ylides resist dimerization and hydrogenation. They show wider singlet–triplet energy gap (ΔΕS–T), broader band gap (ΔΕHOMO–LUMO), and higher nucleophilicity compared to the reported stable N-heterocyclic carbenes. Aromatic cyclic unsaturated ammonium, phosphorus, and sulfur ylide carbenes appear more stable than their saturated cyclic analogs which are in turn more viable than their acyclic counterparts. Copyright © 2014 John Wiley & Sons, Ltd.
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