Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Substituent Effects on the Mass Spectra of ortho-Hydroxyaromatic Aldehyde para-Substituted Benzylidenehydrazones
上田 陽小川 建志小野 行雄
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1976 年 24 巻 12 号 p. 3065-3074

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The difference between the mass spectra of Ar-CH=N-N=CH-Ar derivatives and those of Ar (OH)-CH=N-N=CH-Ar (OH) derivatives was pointed out. Mass spectra of 24 kinds of ortho-hydroxyaromatic aldehyde para-substituted benzylidenehydrazones (Ar (OH)-CH=N-N=CH-Ar'-R) were determined. These compounds were shown to have several kinds of characteristic fragment ions ; [Ar (OH)-CH=N]+ (gion), [N=CH-Ar'-R]+ (g'ion), [Ar (OH)-CH=N+H], [Ar (OH)-CH=N-H], [N=CH-Ar'-R+H], [N=CH-Ar'-R+2H]+ and [M-OH]+ (b ion). The relative ion intensities of g, g'and b ions were found to be strongly dependent on the substituent constant. And all of the values of log [g+] / [dM], log [g'+] / [dM], and log [b+] / [dM+] were shown to correlate linearly with σ+. The substituent effect on the value of either log [g'+] / [g+] or log [b+] / [g+] was found to be the reflection of the substituent effect on the difference of ionization potentials of either g· and g'· radicals or g· and b· radicals, respectively.
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© The Pharmaceutical Society of Japan
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