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Rearrangement of aromatic sulfonate anions in the gas phase
Author(s) -
Binkley Roger W.,
Flechtner Thomas W.,
Tevesz Michael J. S.,
Winnik Witold,
Zhong Boyu
Publication year - 1993
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210280708
Subject(s) - heterolysis , chemistry , sulfonate , nucleophile , deprotonation , intramolecular force , photochemistry , dissociation (chemistry) , fragmentation (computing) , medicinal chemistry , sulfur , ion , ring (chemistry) , organic chemistry , catalysis , sodium , computer science , operating system
Collisionally activated dissociation of deprotonated aromatic sulfonic acids in the gas phase causes rearrangement and fragmentation to produce the corresponding phenoxide ions. The mechanism for this reaction has been investigated and the results of this study favor initial intramolecular nucleophilic addition of a sulfonate oxygen atom to the aromatic ring, a process which is followed by heterolytic cleavage of the carbon–sulfur bond to rearomatize the ring. The product from this addition–elimination sequence is the anion of a sulfurous acid half‐ester, which loses SO 2 to generate the corresponding phenoxide ion.