Synthesis and tautomerism of new 2-substituted benzothiazolyl azo derivatives of 2-naphthol (CROSBI ID 596257)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa
Podaci o odgovornosti
Racane, Livio ; Mihalić, Zlatko ; Cerić, Helena ; Tralić-Kulenović, Vesna
engleski
Synthesis and tautomerism of new 2-substituted benzothiazolyl azo derivatives of 2-naphthol
The azo dyes with a hydroxyl group in conjunction with an azo chromophore exhibit azo-hydrazone tautomerism. The investigation of proton transfer between oxygen and nitrogen atoms is interesting both from the theoretical and practical points of view. The position of the tautomeric equilibrium affects the basic properties of azo dyes such as colour, tone and photostability, as well as their technical properties. We have recently reported the study of azo-hydrazone tautomerism of 6-[(2-hydroxy-1-naphthyl)diazenyl]benzothiazole and 6-[(2-hydroxy-1-naphthyl)diazenyl]-2-methyl benzothiazole jointly by 13C NMR spectroscopy and quantum-mechanical calculations [1]. The Kazo-hydrazone(H)/Kazo-hydrazone(CH3) ratio of 1.3 suggests that the electron-donating substituents move the position of the equilibrium towards the azo form.Here, we report the synthesis and the tautomerism investigation of several new derivatives which exhibit more pronounced equilibrium shift. Using 13C NMR spectroscopy and DFT calculations we estimate the relative proportions of azo and hydrazone forms present at the equilibrium, as well as draw general conclusions about electron density redistribution upon the substitution.
synthesis; benzothiazole; NMR spectroscopy; DFT; azo-hydrazone tautomerism
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Podaci o prilogu
143-143.
2013.
objavljeno
Podaci o matičnoj publikaciji
XXIII. hrvatski skup kemičara i kemijskih inženjera : knjiga sažetaka = XXIII Croatian meeting of chemists and chemical engineers : book of abstracts
Hadžiev, Andrea ; Blažeković, Zdenko
Zagreb: Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI)
978-953-6894-50-5
Podaci o skupu
Hrvatski skup kemičara i kemijskih inženjera (23 ; 2013)
poster
21.04.2013-24.04.2013
Osijek, Hrvatska