Controlled shift in the tautomeric equilibrium of 4-​((phenylimino)​methyl)​naphthalen-​1-​ol

Fadhil S. Kamounah; V Deneva; y Manolova; L Lubenov; V Kuteva; R Nikolova; B Shivachev

doi:10.1016/j.molstruc.2012.11.055

Controlled shift in the tautomeric equilibrium of 4-((phenylimino)methyl)naphthalen-1-ol

Fadhil S. Kamounah, V Deneva, y Manolova, L Lubenov, V Kuteva, R Nikolova, B Shivachev

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

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.

Originalsprog	Engelsk
Artikelnummer	2
Tidsskrift	Journal of Molecular Structure: THEOCHEM
Vol/bind	1036
Udgave nummer	2013
Sider (fra-til)	267-273
Antal sider	7
ISSN	0166-1280
DOI	https://doi.org/10.1016/j.molstruc.2012.11.055
Status	Udgivet - 2013

Emneord

Tautomerism
Schiff bases
Alkali and alkaline earth metal salts
Molecular spectroscopy
X-ray crystallography

Link til dokument

10.1016/j.molstruc.2012.11.055

Citer dette

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title = "Controlled shift in the tautomeric equilibrium of 4-((phenylimino)methyl)naphthalen-1-ol",

abstract = "-((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 mol. spectroscopy (UV-vis absorption/emission and NMR), X-ray crystallog. anal. and quantum-chem. calcns. The results show that with the implementation of a flexible piperidine ring a controlled shift in the tautomeric equil. will be achieved upon protonation/deprotonation in acetonitrile. The addn. of a metal salt also shifts the tautomeric equil., but at very high concns., which is caused not by a complex fo...",

keywords = "Tautomerism, Schiff bases, Alkali and alkaline earth metal salts, Molecular spectroscopy, X-ray crystallography, Tautomerism, Schiff bases, Alkali and alkaline earth metal salts, Molecular spectroscopy, X-ray crystallography",

author = "Kamounah, {Fadhil S.} and V Deneva and y Manolova and L Lubenov and V Kuteva and R Nikolova and B Shivachev",

year = "2013",

doi = "10.1016/j.molstruc.2012.11.055",

language = "English",

volume = "1036",

pages = "267--273",

journal = "Journal of Molecular Structure: THEOCHEM",

issn = "0166-1280",

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}

TY - JOUR

T1 - Controlled shift in the tautomeric equilibrium of 4-((phenylimino)methyl)naphthalen-1-ol

AU - Kamounah, Fadhil S.

AU - Deneva, V

AU - Manolova, y

AU - Lubenov, L

AU - Kuteva, V

AU - Nikolova, R

AU - Shivachev, B

PY - 2013

Y1 - 2013

N2 - -((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 mol. spectroscopy (UV-vis absorption/emission and NMR), X-ray crystallog. anal. and quantum-chem. calcns. The results show that with the implementation of a flexible piperidine ring a controlled shift in the tautomeric equil. will be achieved upon protonation/deprotonation in acetonitrile. The addn. of a metal salt also shifts the tautomeric equil., but at very high concns., which is caused not by a complex fo...

AB - -((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 mol. spectroscopy (UV-vis absorption/emission and NMR), X-ray crystallog. anal. and quantum-chem. calcns. The results show that with the implementation of a flexible piperidine ring a controlled shift in the tautomeric equil. will be achieved upon protonation/deprotonation in acetonitrile. The addn. of a metal salt also shifts the tautomeric equil., but at very high concns., which is caused not by a complex fo...

KW - Tautomerism

KW - Schiff bases

KW - Alkali and alkaline earth metal salts

KW - Molecular spectroscopy

KW - X-ray crystallography

KW - Tautomerism

KW - Schiff bases

KW - Alkali and alkaline earth metal salts

KW - Molecular spectroscopy

KW - X-ray crystallography

U2 - 10.1016/j.molstruc.2012.11.055

DO - 10.1016/j.molstruc.2012.11.055

M3 - Journal article

SN - 0166-1280

VL - 1036

SP - 267

EP - 273

JO - Journal of Molecular Structure: THEOCHEM

JF - Journal of Molecular Structure: THEOCHEM

IS - 2013

M1 - 2