MASS SPECTRA OF OXYGENATED QUINOLINES

1966 ◽  
Vol 44 (7) ◽  
pp. 781-788 ◽  
Author(s):  
D. M. Clugston ◽  
D. B. MacLean
Keyword(s):  
Electron Impact ◽  
Mass Spectra ◽  
Fragmentation Mechanism ◽  
Significant Extent ◽  
Fragmentation Pathways ◽  
Molecular Ion ◽  
One Step ◽  
The Stability ◽  
Hydroxy Compounds ◽  
Fragmentation Patterns

The mass spectra of the monohydroxyquinolines, the monomethoxyquinolines, N-methyl-2-quinolone, and N-methyl-4-quinolone have been recorded. The isomeric hydroxy compounds vary somewhat in the stability of the molecular ion, but all show the same fragmentation mechanism. Two general fragmentation patterns are discernible in the spectrum of each of the monomethoxyquinolines, but there is considerable variation among the isomers in the extent to which the two patterns occur. In addition, 8-methoxyquinoline undergoes a peculiar fragmentation wherein all three methyl hydrogens are lost. The 3-methoxy compound is unusual in that loss of 43 mass units from the molecular ion occurs in one step. Deuterium- and 13C-labelling experiments have proved to be useful in interpreting the fragmentation pathways. The spectra of the two N-methylquinolones prove that O to N methyl rearrangement does not occur to any significant extent upon electron impact.

The mass spectra of trifluoroacetyl-2,5-diketopiperazines. I. cyclo-(-Gly-X), cyclo-(-Ala-X) (X = Gly, Val, Leu, Ile), and cyclo-(-Ala-Ala)

1979 ◽  
Vol 57 (15) ◽  
pp. 2037-2051 ◽  
Author(s):  
George P. Slater ◽  
Lawrence R. Hogge
Keyword(s):  
Mass Spectrum ◽  
Mass Spectra ◽  
High Resolution Data ◽  
Fragmentation Pathways ◽  
Molecular Ion ◽  
Metastable Ions ◽  
Fragmentation Patterns ◽  
The Individual ◽  
Derivatives Of ◽  
Resolution Data

The trifluoroacetyl derivatives of the 2,5-diketopiperazines cyclo-(-Gly-X), cyclo-(-Ala-X) (X = Gly, Val, Leu, Ile), and cyclo-(-Ala-Ala) were examined by GC–MS. The molecular ion was readily detectable only for TFA-cyclo-(-Gly-Gly) (m/e 306, 9%). For those compounds containing a valyl or leucyl/isoleucyl residue the ion of highest mass in the spectrum was formed by elimination of C3H6 or C4H8, respectively, from the molecular ion. In the TFA-cyclo-(-Gly-X) series this ion corresponded to the molecular ion of TFA-cyclo-(Gly-Gly) (m/e 306), and in the TFA-cyclo-(-Ala-X) series, to the molecular ion of TFA-cyclo-(-Ala-Gly) (m/e 320). The fragmentation patterns proposed for these compounds are based on the further degradation of these parent ions so that each compound within a series has a similar mass spectrum. However, sufficient differences were detectable in the various spectra to permit identification of the individual DKP's.Many of the fragmentation pathways devised to explain the mass spectra were supported by high resolution data and appropriate metastable ions.

scholarly journals Electron Impact Ionization Mass Spectra of 3-Amino 6-Chloro2-methyl Quinazolin-4-(3H)-one Derivative

2021 ◽  
pp. 1-5
Author(s):  
Osarumwense Peter Osarodion ◽  
◽  
Omotade Treasure Ejodamen ◽  
Keyword(s):  
Electron Impact ◽  
Mass Spectra ◽  
Impact Ionization ◽  
Cyclic Compound ◽  
Electron Impact Ionization ◽  
Ionization Mass ◽  
Fragmentation Pattern ◽  
Molecular Ion ◽  
Mass Spectral ◽  
Characteristic Fragmentation

Looking at the previous studies on quinazolinones derivatives, only limited information’s are available on their mass spectral along with the preparation of novel quinazolin-4-(3H)-one derivatives The condensation of Methyl-2-amino-4-Chlorobenzoate with acetic anhydride yielded the cyclic compound 2-methyl 7-Chloro-1, 3-benzo-oxazine-4-one (1) which further produce 3-Amino-2-Methyl 7-Chloro quinazolin-4(3H)-ones (2) via the reaction with hydrazine hydrate. The compounds synthesized were unequivocally confirmed by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography-Mass spectrophotometry and Elemental analysis. Discussion: The molecular ion of m/z 235 fragments to give m/z 220 by loss of –NH group. The ion of m/z 220 was broken to give m/z 206 by losing CH2 group and fragment to m/z 177 by loss of HCO. This fragmented to m/z 162 by loss of –CH3 group and then m/z 136 by loss of CN group. The loss of O gave m/z 120 which fragment to give m/z 93 by loss of –HCN and finally gave m/z 65 by loss of CO group. Conclusion: The electron impact ionization mass spectra of compound 2show a weak molecular ion peak and a base peak of m/z 235resulting from a cleavage fragmentation. Compound 2 give a characteristic fragmentation pattern. From the study of the mass spectra of compound 2, it was found that the molecular ion had fragmented to the m/z 220. The final fragmentation led to ion of m/z 93 and ion of mass m/z 65, respectively

Chemical Ionization Mass Spectrometry of Organophosphorus Insecticides

1974 ◽  
Vol 57 (5) ◽  
pp. 1050-1055 ◽  
Author(s):  
Roy L Holmstead ◽  
John E Casida
Keyword(s):  
Mass Spectrometry ◽  
Electron Impact ◽  
Mass Spectra ◽  
Chemical Structure ◽  
Chemical Ionization ◽  
Ionization Mass Spectrometry ◽  
Chemical Ionization Mass Spectrometry ◽  
Ionization Mass ◽  
Organophosphorus Insecticides ◽  
Fragmentation Patterns

Abstract The chemical ionization (CI) mass spectra of 15 important organophosphorus insecticides and 14 of their major metabolites are discussed in relation to the effect of chemical structure on fragmentation patterns. The fragments obtained with CI are sometimes quite different from those formed on electron impact and, in general, simpler spectra are obtained with CI.

The isolation of 11-oxotetrahydrorhombifoline from Ormosia coutinhoi and a study of its mass spectrum

1967 ◽  
Vol 45 (7) ◽  
pp. 751-757 ◽  
Author(s):  
Stewart McLean ◽  
A. G. Harrison ◽  
D. G. Murray
Keyword(s):  
Mass Spectrum ◽  
Electron Impact ◽  
Mass Spectra ◽  
Equilibrium Theory ◽  
Side Chain ◽  
Fragmentation Reaction ◽  
Quasi Equilibrium ◽  
Molecular Ion ◽  
Dihydro Derivative ◽  
A Minor

11-Oxotetrahydrorhombifoline (I) has been isolated from the alkaloidal extract of the bark of Ormosia coutinhoi, and its dihydro derivative II has been prepared. An examination of the mass spectra of these compounds and of their 3,3-d2 derivatives has led to the elucidation of the course of the major electron impact induced fragmentations undergone by the molecules. The main fragmentation of I leads to loss of C3H5 from the side chain to form an ion of m/e 221, with a minor path involving a central fission of the molecular ion to form an ion of m/e 150. The mass spectrum of II shows that the loss of C3H7 to form the ion of m/e 221 is a minor process, the main fragmentation reaction involving a central fission to form an ion of m/e 152 analogous to the ion of m/e 150 from I. This change in the spectrum is shown to be consistent with predictions based on the quasi-equilibrium theory of mass spectra.

Fragmentation pathways in the mass spectra of isomeric phenylazoxypyridine-N-oxides

1992 ◽  
Vol 70 (4) ◽  
pp. 1028-1032 ◽  
Author(s):  
Nigel J. Bunce ◽  
H. Stewart McKinnon ◽  
Randy J. Schnurr ◽  
Sam R. Keum ◽  
Erwin Buncel
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Electron Impact ◽  
Mass Spectra ◽  
Chemical Reduction ◽  
Ion Source ◽  
Tandem Mass ◽  
Mass Spectral Fragmentation ◽  
Fragmentation Pathways ◽  
Mass Spectral

The mass spectral fragmentation pathways of a series of phenylazoxypyridine-N-oxides have been studied under electron impact conditions using tandem mass spectrometry. Besides simple C—N cleavages, the azoxypyridine-N-oxides undergo deep-seated rearrangements directly from the molecular ion. In addition, the spectra are complicated by a purely chemical reduction of the N—O functionalities that occurs in the ion source prior to ionization.

Mass spectra of 4,4-dimethyl-A-homocholestane-3,5- and 3,4a diols and their derivatives

1982 ◽  
Vol 47 (12) ◽  
pp. 3328-3338
Author(s):  
Antonín Trka ◽  
Helena Velgová
Keyword(s):  
Mass Spectrum ◽  
Electron Impact ◽  
Mass Spectra ◽  
Neutral Fragment ◽  
Molecular Ion ◽  
Impact Fragmentation ◽  
Fragmentation Processes

Partial mass spectra of the following 4,4-dimethyl-A-homocholestane derivatives are given: 3,5-epoxides I and II, 3,5-diols III-VI, 3-methoxy-5-ols VII-IX, 3-acetoxy-5-ol X, 3,4a-diols XI-XIV, 3-acetoxy-4a-ols XV-XVIII and 4,4-[2H6]-dimethyl-3,4a-diol XIX, and their electron impact fragmentation investigated. The mass spectra of epoxides I and II, diols III-VI and acetate X are very similar. Considerable differences in mass spectra of methoxy derivatives VII-IX are explained by two mechanisms of elimination of CH3OH from M+. The same similarity of the fragmentation processes and the mass spectra is also observed in diols XI-XIV and acetates XV-XVIII. For the formation of the characteristic ion m/z 288 a fragmentation scheme containing an usual cleavage of the rings A, B, and C is proposed. On the basis of comparison with the mass spectrum of the 4,4-[2H6]dimethyl analogue XIX it was shown that the ion m/z 361 in the mass spectra of diols XI-XIV is formed by elimination of the neutral fragment C6H13 from A-ring of the molecular ion, the last process being accompanied by the 3-hydroxyl transfer from A-ring to the rest of the molecular ion.

Mass Spectra of Fifteen Chlorinated Aromatic Fungicides

1971 ◽  
Vol 54 (1) ◽  
pp. 178-186
Author(s):  
O Hutzinger ◽  
W D Jamieson ◽  
S Safe
Keyword(s):  
Electron Impact ◽  
Mass Spectra ◽  
Molecular Ions ◽  
Chlorine Atoms ◽  
Fragmentation Patterns

Abstract Fragmentation patterns on electron impact of 15 chlorinated aromatic fungicides were investigated. In most cases strong molecular ions were obtained and the peak clusters due to the 35Cl and 37Cl isotopes and the number of chlorine atoms in the molecule were highly characteristic. Many of the polychlorinated fungicides give ions (e.g., C6Cl4, C6Cl3, C6Cl2, C6Cl, and C6 (CN)2) whose structures can be best represented as acyclic polyunsaturated moieties.

The Fragmentation Mechanism of Cyclobutanol

1973 ◽  
Vol 51 (14) ◽  
pp. 2342-2346 ◽  
Author(s):  
John L. Holmes ◽  
Robin T. B. Rye
Keyword(s):  
Hydrogen Atom ◽  
Mass Spectra ◽  
Fragmentation Mechanism ◽  
Hydrogen Atoms ◽  
Specific Mechanism ◽  
Molecular Ion ◽  
Random Manner ◽  
Hydroxyl Hydrogen

The mass spectra of cyclobutanol and three 2H labelled analogs have been studied. The losses of C2H4 and C2H5• from the molecular ion involve specific fragmentations. Only CH3• loss from the α-cleaved molecular ion2 clearly involves hydrogen atom scrambling; this fragmentation also proceeds by a specific mechanism involving C-2 and hydroxyl hydrogen atoms. Loss of water from the molecular ion involves all the hydrogen atoms but in a complex, non-random manner.

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