dc.contributor.author | Remeš, Marek | |
dc.contributor.author | Roithová, Jana | |
dc.contributor.author | Schröder, Detlef | |
dc.contributor.author | Cope, Elizabeth D. | |
dc.contributor.author | Perera, Chamani | |
dc.contributor.author | Senadheera, Sanjeewa N. | |
dc.contributor.author | Stensrud, Kenneth F. | |
dc.contributor.author | Ma, Chi-cheng | |
dc.contributor.author | Givens, Richard S. | |
dc.date.accessioned | 2017-04-12T17:44:45Z | |
dc.date.available | 2017-04-12T17:44:45Z | |
dc.date.issued | 2011-04-01 | |
dc.identifier.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 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/23639 | |
dc.description.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. | en_US |
dc.publisher | American Chemical Society | en_US |
dc.rights | This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo1025223.. | en_US |
dc.subject | Collisional activation | en_US |
dc.subject | Favorskii rearrangement | en_US |
dc.subject | P-hydroxyphenacyl compounds | en_US |
dc.subject | Mass spectrometry | en_US |
dc.title | Gas-phase Fragmentation of Deprotonated p-Hydroxyphenacyl Derivatives | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Cope, Elizabeth D. | |
kusw.kuauthor | Perera, Chamani | |
kusw.kuauthor | Senadheera, Sanjeewa N. | |
kusw.kuauthor | Stensrud, Kenneth | |
kusw.kuauthor | Ma, Chi-cheng | |
kusw.kuauthor | Givens, Richard S. | |
kusw.kudepartment | Chemistry | en_US |
dc.identifier.doi | 10.1021/jo1025223 | en_US |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.rights.accessrights | openAccess | |