Benzo[c]cinnoline derivatives. IV. Substituent effects in the mass spectra of substituted Benzo[c]cinnolines

1968 ◽  
Vol 21 (5) ◽  
pp. 1233 ◽  
Author(s):  
JH Bowie ◽  
GE Lewis ◽  
JA Reiss

The mass spectra of a series of benzo[c]cinnoline derivatives are reported and discussed. The spectra are useful for analytical purposes, as all compounds give pronounced molecular ions, and the fragmentation processes generally occur without skeletal-rearrangement. Many benzo[c]cinnolines which are substituted in the 4-position may be differentiated from other isomers by the presence of "proximity- effects" in their mass spectra.


1968 ◽  
Vol 21 (8) ◽  
pp. 2031 ◽  
Author(s):  
JH Bowie ◽  
SO Lawesson ◽  
BS Larse ◽  
GE Lewis ◽  
G Schroll

The negative-ion mass spectra of aromatic azoxy compounds, nitrones, and N-oxides exhibit pronounced molecular ions and simple fragmentation processes. No skeletal-rearrangement fragments are produced upon electron impact, in marked contrast to those exhibited in the positive-ion spectra of these compounds.



1973 ◽  
Vol 26 (1) ◽  
pp. 195 ◽  
Author(s):  
JH Bowie

The technique of Beynon1,2 has been used to determine the ?doubly charged ion? mass spectra of a series of benzoic acid derivatives. A general feature of all spectra is the presence of pronounced M-CO species. The losses of carbon monoxide from the doubly charged molecular ions of m- amino- and m-hydroxy-benzoic acids originate mainly from the carboxyl groups, whereas the predominant loss from benzoic acid involves the aryl ring system. The spectra of anthranilates and salicylates contain peaks produced by characteristic proximity effects.



1967 ◽  
Vol 20 (8) ◽  
pp. 1601 ◽  
Author(s):  
JH Bowie ◽  
RG Cooks ◽  
GE Lewis

The mass spectra of 15 aromatic azoxy compounds are reported and discussed. The spectra exhibit pronounced molecular ions, and fragmentation modes which are produced by both simple cleavage and complex skeletal reorganization processes.



1969 ◽  
Vol 22 (1) ◽  
pp. 153 ◽  
Author(s):  
JH Bowie ◽  
F Duus ◽  
S Lawesson ◽  
FCV Larsson ◽  
J+ Madsen

The negative-ion mass spectra of thioglycollic esters and S- alkylthioglycollic acids exhibit ions produced by simple cleavage and/or cleavage with hydrogen rearrangement. Similar spectra of arylsulphinylamines show pronounced molecular ions together with simple cleavage fragments. No skeletal-rearrangement fragments are present in the negative-ion spectra, in marked contrast with those observed in the corresponding positive-ion spectra.



1967 ◽  
Vol 20 (8) ◽  
pp. 1613 ◽  
Author(s):  
JH Bowie ◽  
RG Cooks ◽  
S Lawesson ◽  
G Schroll

The mass spectra of 37 imidazoles are reported and discussed. The spectra exhibit pronounced molecular ions and characteristic fragmentation patterns. The fragmentation modes have been substantiated by deuterium labelling, exact mass measurements, and appropriate metastable ions. Skeletal rearrangement fragments are rare in these spectra; consequently mass spectrometry is useful for structure elucidation of imidazoles.



1967 ◽  
Vol 20 (6) ◽  
pp. 1179 ◽  
Author(s):  
JH Bowie ◽  
RG Cooks ◽  
RH Prager ◽  
HM Thredgold

The mass spectra of 34 acridones have been determined and interpreted with the aid of both high-resolution measurements and deuterium labelling studies. The spectra contain pronounced molecular ions and are free of skeletal rearrangement fragments. The fragmentation patterns are dependent on the nature and position of substituents, and therefore mass spectrometry can be a useful aid to structure determination in this class of naturally occurring compounds.



1982 ◽  
Vol 47 (11) ◽  
pp. 2946-2960 ◽  
Author(s):  
Antonín Trka ◽  
Alexander Kasal

Partial EI-mass spectra of 3β-hydroxy- and 3β-acetoxy-5α-cholestanes substituted in positions 5α-, 6β- or 5α,6β- with a hydroxyl group or halogen atoms (fluorine, chlorine, bromine) are presented. The molecular ions of 5α,6β-disubstituted derivatives of 3β-hydroxy-5α-cholestane (or of its 3-acetate) are considerably more stable than the corresponding monosubstituted derivatives if at least one of the pair of the vicinal substituents is chlorine or fluorine. This increase in stability, most striking in 5α- and 6β-fluoro compounds, is explained by the inductive effect.



1982 ◽  
Vol 47 (10) ◽  
pp. 2768-2778
Author(s):  
Antonín Trka ◽  
Helena Velgová

Partial electron impact induced mass spectra are given of 3α-hydroxy-, 3β-hydroxy-, 3β-methoxy-, 3α-acetoxy- and 3β-acetoxy-4,4-dimethyl-A-homo-4a,6-cholestadienes, 3α,5α-epoxy-4,4-dimethyl-A-homo-5-cholestane, isomeric 4,4-dimethyl-A-homo-5-cholestene-3α(β),4aα(β)-diols, their 3-acetoxy derivatives and 3-methyl ethers. The fragmentation of the molecular ions of these substances involves the usual elimination of substituents (in the form of H2O, CH3OH, CH3COOH, CH2CO), but the most abundant and characteristic ions are products of the contraction of ring A (to a six- or five-membered one), accompanied by expulsion of a fragment containing the carbon atom C(4) with both methyls.



1967 ◽  
Vol 20 (4) ◽  
pp. 689 ◽  
Author(s):  
JH Bowie ◽  
RG Cooks ◽  
P Jakobsen ◽  
S Lawesson ◽  
G Schroll

The mass spectra of representative series of simple alkyl acetoacetates, alkyl acetothioacetates, and some unsaturated esters derived from unsaturated alcohols or phenols are reported and discussed. The fragmentation schemes have been established by high resolution measurements, appropriate metastable ions, and by deuterium and 18O labelling. Many of the spectra show significant skeletal rearrangement fragments arising from either loss of carbon monoxide or carbon dioxide.





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