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Cycloreversion and other gas‐phase reactions of neutral and cationic pyrrolidine‐fused chlorins and isobacteriochlorins under ion bombardment and electrospray
Author(s) -
Izquierdo Raul A.,
Barros Cristina M.,
SantanaMarques M. Graça,
Correia A. J. Ferrer,
Silva Ana M. G.,
Tomé Augusto C.,
Silva Artur,
Neves M. Graça P. M. S.,
Cavaleiro J. A. S.
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.1663
Subject(s) - chemistry , pyrrolidine , cationic polymerization , photochemistry , electrospray , porphyrin , ion , medicinal chemistry , polymer chemistry , organic chemistry
Neutral and cationic pyrrolidine‐fused chlorins and isobacteriochlorins derived from meso ‐tetrakis(pentafluorophenyl)porphyrin undergo cycloreversion reactions in the gas phase, either when desorbed from a liquid matrix by ion bombardment or when electrosprayed. Cycloreversion occurs through loss of either neutral or charged moieties, with and without hydrogen and methyl radical migration, and both as high‐ and low‐energy collision processes. For the doubly charged isobacteriochlorin, one‐electron reduction with methyl loss occurs under ion bombardment and electrospray, through hypervalent pyrrolidinium radical formation. Copyright © 2004 John Wiley & Sons, Ltd.