Premium
Ion‐neutral complex‐mediated hydrogen exchange in ionized n ‐butanol: A mechanism for ‘non‐specific’ hydrogen migrations
Author(s) -
McAdoo David J.,
Hudson Charles E.
Publication year - 1987
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.1210220908
Subject(s) - hydrogen , chemistry , ion , cyclobutane , ionization , ring (chemistry) , photochemistry , stereochemistry , organic chemistry
Water elimination from ionized n ‐butanol reflects near randomization of all hydrogens in ions decomposing after ∼10 −5 s. This probably takes place in ion‐neutral complexes by formation of a cyclobutane ion–H 2 O complex and/or rearrangement within [C 4 H 8 ] + ˙ in open‐chain [C 4 H 8 + ˙H 2 O] complexes, in either case accompanied by hydrogen exchange between water and open‐chain hydrocarbon moieties. Extensive hydrogen rearrangements in which restraints on conventional transition‐state ring size have little apparent influence may generally be ion–neutral complex‐mediated processes.