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Gas-Phase Fragmentation of Deprotonated p-Hydroxyphenacyl Derivatives.
- Source :
-
Journal of Organic Chemistry . 4/1/2011, Vol. 76 Issue 7, p2180-2186. 7p. - Publication Year :
- 2011
-
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 the 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 76
- Issue :
- 7
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 63229859
- Full Text :
- https://doi.org/10.1021/jo1025223