کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1406139 | 1501778 | 2013 | 7 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Controlled shift in the tautomeric equilibrium of 4-((phenylimino)methyl)naphthalen-1-ol Controlled shift in the tautomeric equilibrium of 4-((phenylimino)methyl)naphthalen-1-ol](/preview/png/1406139.png)
4-((Phenylimino)methyl)naphthalen-1-ol and 4-((phenylimino)methyl)-2-(piperidin-1-ylmethyl)naphthalen-1-ol have been synthesized and their tautomeric properties were investigated using molecular spectroscopy (UV–Vis absorption/emission and NMR), X-ray crystallographic analysis and quantum-chemical calculations. The results show that with the implementation of a flexible piperidine ring a controlled shift in the tautomeric equilibrium will be achieved upon protonation/deprotonation in acetonitrile. The addition of a metal salt also shifts the tautomeric equilibrium, but at very high concentrations, which is caused not by a complex formation, but a special effect of the salt addition.
► 4-((Phenylimino)methyl)-2-(piperidin-1-ylmethyl)naphthalen-1-ol was studied.
► The controlled shift of the tautomeric equilibrium through structural modifications was achieved.
► The inclusion of the piperidine ring leads to shift of the equilibrium to the enol tautomer.
► Upon protonation the equilibrium shifts to the keto tautomer in a controlled and reversible manner.
► The salt addition leads to shift in the tautomeric equilibrium, independly on the kind of salt used.
Journal: Journal of Molecular Structure - Volume 1036, 27 March 2013, Pages 267–273