The formation of RCCCO and CCC(O)R (R = Me, Ph) neutral radicals from ionic precursors in the gas phase: the rearrangement of CCC(O)Ph | Zendy

Peppe Salvatore | Zendy; McAnoy Andrew M. | Zendy; Dua Suresh | Zendy; Bowie John H. | Zendy

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The formation of RCCCO and CCC(O)R (R = Me, Ph) neutral radicals from ionic precursors in the gas phase: the rearrangement of CCC(O)Ph

Author(s) -

Peppe Salvatore,

McAnoy Andrew M.,

Dua Suresh,

Bowie John H.

Publication year - 2004

Publication title -

rapid communications in mass spectrometry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.528

H-Index - 136

eISSN - 1097-0231

pISSN - 0951-4198

DOI - 10.1002/rcm.1425

Subject(s) - chemistry , radical , microsecond , gas phase , exothermic reaction , decomposition , ionic bonding , medicinal chemistry , photochemistry , computational chemistry , ion , organic chemistry , physics , astronomy

Neutrals MeCCCO, CCC(O)Me, PhCCCO and CCC(O)Ph have been made by neutralisation of [MeCCCO] + , [CCC(O)Me] − , [PhCCCO] + and [CC(CO)Ph] − . Neutrals MeCCCO, CCC(O)Me and PhCCCO are stable for the microsecond duration of the neutralisation experiment. A joint experimental and theoretical study (energies calculated at the B3LYP/aug‐cc‐pVDZ//B3LYP/6‐31G(d) level of theory) suggests that the neutral radical CCC(O)Ph rearranges via a four‐centred ipso radical cyclisation/ring opening to form the isomer PhCCCO in an exothermic reaction. 13 C labelling confirms that the rearrangement does not involve O migration. Some of the PhCCCO radicals formed in this reaction are sufficiently energised to effect decomposition to give PhCC and CO. Copyright © 2004 John Wiley & Sons, Ltd.

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