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• W2016183757 abstract "Abstract Tandem mass spectrometry experiments show that N -formylethanolamine molecular ions HOCH 2 CH 2 NHC(H) O + ( FE 1) lose C 2 H 3 O , CH 2 O and H 2 O to yield m / z 46 ions HC(OH)NH 2 + , m / z 59 ions CH 2 N(H)CHOH + , and m / z 71 N -vinylformamide ions CH 2 C(H)N(H)CHO + . A detailed mechanistic study using the CBS-QB3 model chemistry reveals that the readily generated 1,5-H shift isomer HOCHCH 2 N(H)C(H)OH + ( FE 2) and hydrogen-bridged radical cations (HBRCs) act as key intermediates in a ‘McLafferty + 1′ type rearrangement that yields the m / z 46 ions. The co-generated C 2 H 3 O neutrals are predicted to be vinyloxy radicals CH 2 CHO in admixture with CH 3 C O generated by quid-pro-quo (QPQ) catalysis. A competing C−C bond cleavage in FE 1 leads to HBRC [CH 2 N(H)C(H) O-⋯H⋯O CH 2 ] + , which serves as the direct precursor for CH 2 O loss. In addition, ion FE 2 also communicates with a myriad of ion–molecule complexes of vinyl alcohol and formimidic acid whose components may recombine to form distonic ion FE 3, HOCH(CH 2 )N(H)C(H)OH + , which loses H 2 O after undergoing a 1,5-H shift. Further support for these proposals comes from experiments with D- and 18 O-labelled isotopologues. Previously reported proposals for the H 2 O and CO losses from protonated N -formylethanolamine are briefly re-examined." @default.
• W2016183757 created "2016-06-24" @default.
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• W2016183757 date "2011-09-01" @default.
• W2016183757 modified "2023-09-25" @default.
• W2016183757 title "The dissociation chemistry of low-energy N-formylethanolamine ions: Hydrogen-bridged radical cations as key intermediates" @default.
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• W2016183757 doi "https://doi.org/10.1016/j.ijms.2011.05.011" @default.
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