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Gas-phase Fragmentation of Deprotonated p-Hydroxyphenacyl Derivatives
Remeš, Marek Roithová, Jana Schröder, Detlef Cope, Elizabeth D. Perera, Chamani Senadheera, Sanjeewa N. Stensrud, Kenneth F. Ma, Chi-cheng Givens, Richard S.
Remeš, Marek
Roithová, Jana
Schröder, Detlef
Cope, Elizabeth D.
Perera, Chamani
Senadheera, Sanjeewa N.
Stensrud, Kenneth F.
Ma, Chi-cheng
Givens, Richard S.
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Abstract
Electrospray ionization of methanolic solutions of p-hydroxyphenacyl derivatives HO-C6H4-C(O)-CH2-X (X = leaving group) provides abundant signals for the deprotonated species which are assigned to the corresponding phenolate anions −O-C6H4-C(O)-CH2-X. Upon collisional activation in the gas phase, these anions inter alia undergo loss of a neutral “C8H6O2” species
concomitant with formation of the corresponding anions X−. The energies required for the loss of neutral roughly correlate with the gas phase acidities of the conjugate acids (HX). Extensive theoretical studies performed for X = CF3COO in order to reveal the energetically most favorable pathway for the formation of neutral “C8H6O2” suggest three different routes of similar energy
demands, involving a spirocyclopropanone, epoxide formation, and a diradical, respectively.
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Date
2011-04-01
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American Chemical Society
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Cope_2011.pdf
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Keywords
Collisional activation, Favorskii rearrangement, P-hydroxyphenacyl compounds, Mass spectrometry
Citation
Remeš, M., Roithová, J., Schröder, D., Cope, E. D., Perera, C., Senadheera, S. N., … Givens, R. S. (2011). Gas-phase Fragmentation of Deprotonated p-Hydroxyphenacyl Derivatives. The Journal of Organic Chemistry, 76(7), 2180–2186. http://doi.org/10.1021/jo1025223