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Mass-Spectrometric Study on Ion-Molecule Reactions of CF3+ with Furan and Thiophene at Near-Thermal Energies

The branching ratios of product ions for the reactions of CF3+ with furan and thiophene were determined by using an ion-beam apparatus. The main reaction channels proceed via α- and β-trifluoromethylated intermediates (C-adducts), followed by HF elimination, CO elimination, and CO + HF elimination for furan, and followed by HF elimination for thiophene. Semiempirical MNDO calculations of heats of formation of various intermediates and products were carried out to explore possible mechanisms. It was concluded that the CO and CO + HF eliminations for furan occur through a cleavage of a C–O skeletal bond of the C-adducts. The lack of CO and CO + HF elimination channels for thiophene was explained by the fact that the ring-opening and ring-contraction channels are energetically closed.