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Heteroaromatic species are commonly found in complex gaseous mixtures, from tobacco smoke to petroleum and asphaltene combustion products. At high temperatures, C–H bond rupture produces various dehydro radical isomers. We have used the spin–flip formulation of equation-of-motion coupled cluster theory with single and double substitutions (EOM-SF-CCSD) to characterize the energies and wave functions of the lowest lying singlet and triplet states of the diradical (2,3), (2,4), (2,5), and (3,4) di-dehydro isomers of pyrrole, furan, and thiophene. In all cases, these diradicals are minima on the broken-symmetry ωB97X-D/cc-pVDZ potential energy surface. In most cases, the diradical geometries distort to enhance through-space or through-bond coupling in the singlet states and to avoid Coulombic or exchange repulsion in the triplet states. EOM-SF-CCSD results indicate that all diradical isomers are two-configurational, closed shell singlet states. The only exceptions to this are for (2,3) and (2,4) thiophene and (2,3) pyrrole, which each contain more than two configurations. In all cases, the leading term in the multiconfigurational diradical wave function doubly occupies the symmetric radical σ orbital, indicative of either through-space or 1,3 through-bond coupling. We utilized the nucleus-independent chemical shift (NICS) approach to qualitatively assess aromaticity and find that this property varies and may be related to the energetic splittings in these diradical isomers.