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Isomerization reaction of [C 6 H 6 C 4 H 9 + ] π complexes
Author(s) -
Berthomieu Dorothée,
Audier HenriEdouard,
Monteiro Candida,
Denhez JeanPierre,
Maquestiau A.
Publication year - 1991
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.1290050908
Subject(s) - protonation , chemistry , isomerization , metastability , dissociation (chemistry) , medicinal chemistry , ion , photochemistry , stereochemistry , organic chemistry , catalysis
Metastable protonated butylbenzenes have been studied by extensive labelling and kinetic energy release measurements. Protonated s‐butylbenzene isomerizes by 1–2 hydrogen shift to the π complex [C 6 H 6 S C 4 H 9 + ], and the S C 4 H 9 +cation rearranges to t‐C 4 H 9 + . The interconversion between [C 6 H 6 S C 4 H 9 + ] and [C 6 H 7 +C 4 H 8 ] ion/neutral complexes is demonstrated. Protonated t‐butylbenzene reacts without hydrogen exchange to give t‐C 4 H 9 + , while protonated n‐butylbenzene isomerizes to s‐butylbenzene prior to dissociation. Protonated iso‐butylbenzene isomerizes to protonated t‐butylbenzene and to protonated s‐butylbenzene. In the 2nd field‐free region, the dissociation of this last form predominates.