Journal of the American Chemical Society p. 7696 - 7701 (1989)
Update date:2022-08-16
Topics:
Turecek, Frantisek
Drinkwater, Donald E.
McLafferty, Fred W.
The kinetically unstable molecules methanesulfenic acid (CH3SOH, 1) and its ylide isomer ((-)CH2(+)SHOH, 2) and the isomeric radicals CH3SO(.) and (.)CH2SOH exist as distinct species in the gas phase.CH3SOH was generated by flash-vacuum pyrolysis of methyl tert-butyl sulfoxide and by neutralization of the corresponding cation radical.The ylide (-)CH2(+)SHOH was prepared by neutralizaton of the distonic ion, (.)CH2(+)SHOH, generated from di-n-butyl sulfoxide by double hydrogen rearrangement.Upon collisional activation CH3SOH decomposes to CH3(.) and (.)SOH, while(-)CH2(+)SHOH affords mainly (.)CH2SH and (.)OH.Collisionally activated dissociation (CAD) spectra of the corresponding ions also distinguish these (C,H4,O,S)(.+) isomers.The isomeric radicals CH3SO(.) and (.)CH2SOH and ions CH3SO(+) and CH2SOH(+) were characterized through their neutralization-reionization and CAD mass spectra, respectively.Decomposition mechanisms consistent with deuterium labeling are proposed, and the relative stabilities of the (C,H4,O,S) isomers are estimated by MNDO calculations.
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