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• W2123278290 endingPage "8541" @default.
• W2123278290 startingPage "8533" @default.
• W2123278290 abstract "This work represents the next step in the studies of heterogeneous substitution effects in cyanohalo radicals and carbenes. Negative-ion photoelectron imaging was used to investigate the substituted radical and carbene derivatives of fluoroacetonitrile. We report a closed-shell singlet ground state for cyanofluorocarbene, FCCN, with a directly measured adiabatic electron affinity EA = 2.081 ± 0.002 eV and a singlet–triplet gap of ΔES-T = 0.42 ± 0.04 eV, estimated through a combination of experimental and theoretical results. The open-shell singlet 1A″ state was also observed experimentally. The cyanofluoromethyl radical, FC(H)CN, was similarly estimated to have an EA of 1.53 ± 0.08 eV. This value was used to estimate the C–H bond dissociation energy (BDE) of fluoroacetonitrile, DH298 = 90.7 ± 2.8 kcal mol–1. The results are discussed in comparison with results for other fluoro- and cyano-substituted radicals and carbenes, and in light of our recent work on the radical and carbene derivatives of chloroacetonitrile. The estimated ΔES-T of FCCN agrees well with the general trend of similar carbenes. We also find that, similar to chloroacetonitrile, the low C–H BDE of fluoroaceotnitrile indicates a synergistic stabilization of the corresponding radical by a π donor (halogen) and π acceptor (CN)." @default.
• W2123278290 created "2016-06-24" @default.
• W2123278290 creator A5001608939 @default.
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• W2123278290 date "2014-04-28" @default.
• W2123278290 modified "2023-09-30" @default.
• W2123278290 title "Heterogeneously Substituted Radicals and Carbenes: Photoelectron Imaging of the FC(H)CN^– and FCCN^– Anions" @default.
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• W2123278290 doi "https://doi.org/10.1021/jp5024229" @default.
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• W2123278290 hasPublicationYear "2014" @default.
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