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Substituent Effect on the Tautomerization of 1‐Arylazonaphthalen‐2‐ols by Mass Spectrometric Analysis
Author(s) -
Lin ShawTao,
Lin LeeHui,
Lin YiCang,
Ding MeiFan
Publication year - 2015
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201400305
Subject(s) - chemistry , substituent , fragmentation (computing) , electron ionization , polyatomic ion , tautomer , ion , mass spectrum , hammett equation , ionization , computational chemistry , mass spectrometry , polar effect , analytical chemistry (journal) , reaction rate constant , photochemistry , medicinal chemistry , organic chemistry , kinetics , chromatography , physics , quantum mechanics , computer science , operating system
An electron‐ionization (EI) mass spectra of a series of 1‐arylazonaphthalen‐2‐ols was obtained for studying the substituent effect on the fragmentation. The correlation between the ratio, molecular ion and fragment ion, and Hammett’s constants is applied to examine the effect of the substituent on the fragmentation. The negative correction between the ratio, I molecular ion /(I 171amu + I 143amu + I 115amu ), and Hammett’s constants indicates an electron‐withdrawing group destabilized the molecular ion. An unusual long‐range hydrogen transfer demonstrates an important role in the fragmentation process