One-electron oxidation of [CCOCC]–· in the gas phase forms stable and decomposing forms of CCCCO

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2005

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Fitzgerald, M.
Dua, S.
Bowie, J.

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Organic and Biomolecular Chemistry, 2005; 3(14):2646-2651

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Mark Fitzgerald, Suresh Dua and John H. Bowie

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Abstract

The radical anion [CCOCC]−• may be made in the source of a VG ZAB 2HF mass spectrometer by the reaction between F− (from SF₆) and (CH₃)₃SiC≡COC≡CSi(CH₃)₃. Vertical (Franck–Condon) one-electron oxidation of [CCOCC]−• in the first collision cell produces both singlet and triplet CCOCC. A combination of experiment and molecular modelling (at the CCSD(T)/aug-cc-pVDZ//B3LYP/6-31G* level of theory) gives data which are consistent with the CCOCC neutrals rearranging over small barriers to form singlet and triplet CCCCO in exothermic reactions. Both singlet and triplet CCCCO formed in this way have excess energy. Singlet CCCCO has sufficient excess energy to effect decomposition exclusively to CCC and CO. In contrast, some of the triplet CCCCO neutrals are stable, while others decompose to CCC and CO.

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Copyright © Royal Society of Chemistry 2005 Reproduced by permission of The Royal Society of Chemistry

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