6533b7d1fe1ef96bd125ca91
RESEARCH PRODUCT
Mass spectra of chlorinated esters: 2—Methyl mono- and dichlorobutanoates
Ilpo O.o. Korhonensubject
McLafferty rearrangementChemistryStereochemistryPolyatomic ionDiastereomerBiochemistryMedicinal chemistrySpectral lineIonFragmentation (mass spectrometry)MetastabilityMass spectrumMolecular MedicineInstrumentationSpectroscopydescription
The mass spectral fragmentations of methyl mono- and dichlorobutanates have been studied. Deutrium labelling and metastable ion analysis were used to elucidate the fragmentation mechanisms. The molecular ion peaks of the esters are weak and show only in the spectra of the monochloro isomers. A McLafferty rearrangement gives the base peaks in the spectra of methyl 2-chloro-, 4-chloro- and 4,4-dichlorobutanoate; α-cleavage, [COOCH3]+, in methyl 2,2- and 2,4-dichlorobutanoate; [MCl]+, in methyl 3-chlorobutanoate; [MClHCl]+, in methyl 3,4-dichlorobutanoate; [MClCH2CO]+, in methyl 3,3-dichlorobutanoate and [MClCOOCH3]+˙, in methyl erythro- and threo-2,3-dichlorobutanoate. The mass spectra of the stereoisomers are nearly identical, the loss of a chlorine atom and the McLafferty rearrangement giving the higher peaks in the spectrum of the threo form.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1982-11-01 | Organic Mass Spectrometry |