5-Dehydro-1,3-quinodimethane: A hydrocarbon with an open-shell doublet ground state

L. V. Slipchenko, T. E. Munsch, P. G. Wenthold, and A. I. Krylov
Angew. Chem. Int. Ed. 43, 742 – 745 (2004)

Experimental and theoretical studies of the 5-dehydro-1,3-quinodimethane triradical are described. Theory predicts an open-shell doublet ground state, with three low-spin coupled electrons in three singly occupied molecular orbitals, which is unprecedented electronic structure for a ground state organic triradical. The bond dissociation enthalpy for formation of the triradical from meta-xylylene, which was measured using mass spectrometric methods, indicates an interaction of 1±4 kcal/mol between the unpaired electrons in the σ- and π-systems of the triradical.

Download this paper (PDF, 167 kB)

Related Research

Triradicals and diradicals

Computational studies of electronically excited and open-shell species: Jahn-Teller systems, radicals, diradicals and triradicals