Online citations, reference lists, and bibliographies.

Investigation Of Two O-hydroxy Schiff Bases In Terms Of Prototropy And Radical Scavenging Activity

Ç. A. Kaştaş, G. Kaştaş, A. Güder, M. Gür, H. Muğlu, O. Bueyuekguengoer
Published 2017 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Abstract Two Schiff bases, namely (E)-4,6-dibromo-3-methoxy-2-[(phenylimino)methyl]phenol (1) and (Z)-2,4-dibromo-6-[(4-buthylphenylamino)methylene]-5-methoxycyclohexa-2,4-dienone (2), have been investigated by considering solvent, substituent and temperature dependence of prototropy, and scavenging activities. Experimental (X-ray diffraction, UV–vis and NMR) and computational (DFT) techniques have been used to obtain key data on prototropy and other properties of interest. X-ray and UV–vis results underline the variability in the structural preferences of the compounds with respect to the phase and solvent media conditions. This kind of tautomeric behavior has been elaborated by 1H NMR and 13C NMR experiments performed at room and low temperatures. Radical scavenging properties of two compounds have been probed for their usage potentials as therapeutic agent and ingredient in medicinal and food industries, respectively. For this purpose, three different test methods (DPPH, ABTS•+ and DMPD•+) have been used. It has been found from in vivo and in vitro studies that the compound 2 could be interesting as an active component in pharmaceutical industry or as an additive in food industry when its antiradical activity is considered.
This paper references
10.1246/bcsj.25.411
Vat Dyes of Acenaphthene Series. IV. Condensation of Perylenetetracarboxylic Acid Anhydride with o-Phenylenediamine
T. Maki (1952)
10.1016/S0277-5387(01)00960-3
Electrochemical studies of copper(II) complexes with Schiff-base ligands
S. Zolezzi (2002)
10.1016/1010-6030(95)04182-6
Effect of cyclodextrin complexation on thermochromic Schiff bases
G. Pistolis (1996)
10.1021/ic00196a003
Copper(II) and nickel(II) complexes of unsymmetrical tetradentate Schiff base ligands
R. Atkins (1985)
10.1002/jlac.18641310113
Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen
H. Schiff (1864)
10.1080/0095897042000274733
Mononuclear and binuclear Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes of schiff-base ligands derived from 7-formyl-8-hydroxyquinoline and diaminonaphthalenes
T. M. Ismail (2005)
10.1039/B008789K
Macrocyclic ligand design. X-Ray, DFT and solution studies of the effect of N-methylation and N-benzylation of 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane on its affinity for selected transition and post-transition metal ions
T. Hambley (2001)
10.1016/J.JINORGBIO.2007.06.028
Copper conjugates of nimesulide Schiff bases targeting VEGF, COX and Bcl-2 in pancreatic cancer cells.
Vinita Ambike (2007)
10.1021/ja00404a017
The synthesis, redox properties, and ligand binding of heterobinuclear transition-metal macrocyclic ligand complexes. Measurement of an apparent delocalization energy in a mixed-valent copper(I)copper(II) complex
R. R. Gagne (1981)
10.1023/A:1012047001167
Coordination chemistry and biological activity of nickel(II) and copper(II) ion complexes with nitrogen–sulphur donor ligands derived from S-benzyldithiocarbazate (SBDTC)
M. T. H. Tarafder (2001)
10.1002/anie.199515551
Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals
J. Bernstein (1995)
10.1002/CHIN.199940255
Transferrin As A targeting ligand for liposomes and anticancer drugs.
M. Singh (1999)
Photochromism : molecules and systems
H. Dürr (2003)
10.1016/j.saa.2012.03.004
Molecular structure, spectroscopic investigations, second-order nonlinear optical properties and intramolecular proton transfer of (E)-5-(diethylamino)-2-[(4-propylphenylimino)methyl]phenol: a combined experimental and theoretical study.
B. Koşar (2012)
10.1002/jcc.540070206
An improved set of mndo parameters for sulfur
M. Dewar (1986)
10.1016/j.saa.2013.10.022
Existence of a resonance hybrid structure as a result of proton tautomerism in (±)-(E)-4-bromo-2-[(2,3-dihydroxypropylimino) methyl]phenol racemate.
Çiğdem Albayrak (2014)
10.1039/B201195F
Macrocyclic ligand design. Structure–function relationships involving the interaction of pyridinyl-containing, mixed oxygen–nitrogen donor macrocycles with cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II)
R. R. Fenton (2002)
10.1080/00387019909349976
Fluorescence Characteristics of Schiff Bases Derived from Amino- and Aminoalkylpyridines
Z. Cimerman (1999)
10.1021/ar00172a005
Encoding and decoding hydrogen-bond patterns of organic compounds
M. C. Etter (1990)
10.1021/j100096a001
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
P. Stephens (1994)
10.1063/1.477483
An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules
R. Stratmann (1998)
10.1107/S0567740878011930
Crystal and molecular structure of some thermochromic Schiff bases
I. Moustakali-mavridis (1978)
10.1107/S0108270107003241
Three (E)-2-[(bromophenyl)iminomethyl]-4-methoxyphenols.
A. Ozek (2007)
10.1016/S0020-1693(00)87702-6
High-valent manganese complexes of tetradentate schiff base ligands. ESR-active and ESR-silent dimeric species
C. A. Mcauliffe (1986)
10.1016/J.JPHOTOCHEMREV.2005.12.002
Photochromism of organic compounds in the crystal state
Kiichi Amimoto (2005)
10.1002/POC.1403
Structural and aromatic aspects of tautomeric equilibrium in hydroxy aryl Schiff bases
Aleksander Filarowski (2008)
10.1021/cr60318a002
Synthetic oxygen carriers related to biological systems
R. Jones (1979)
10.1002/QUA.22789
Theoretical and experimental studies on electronic structure, cocrystallization, and intramolecular proton transfer of two tautomers: (E)-2-{[2-(hydroxymethyl)phenylimino]methyl}-5-methoxyphenol and (Z)-6-{[2-(hydroxymethyl)phenylamino] methylene}-3-methoxy-cyclohexa-2, 4-dienone
B. Koşar (2010)
10.1016/S0022-2860(01)00638-X
Solvent effect on intramolecular proton transfer equilibrium in some N-(R-salicylidene)-alkylamines
T. Dziembowska (2001)
10.1042/cs0840407
A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates.
N. J. Miller (1993)
10.1016/j.saa.2011.05.046
Probing the compound (E)-5-(diethylamino)-2-[(4-methylphenylimino)methyl]phenol mainly from the point of tautomerism in solvent media and the solid state by experimental and computational methods.
Çiǧdem Albayrak (2011)
10.1021/ed039p546
Spectrometric identification of organic compounds
R. Silverstein (1963)
10.1107/S0021889897003117
ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI)
L. Farrugia (1997)
10.1016/j.saa.2012.03.058
Single stranded helical chains of C-H⋯π interactions further connected by halogen-halogen interactions of type I to construct supramolecular structure of (E)-5-(diethylamino)-2-[(4-iodophenylimino)methyl]phenol compound.
Gökhan Kaştaş (2012)
10.1107/S160053680500807X
2‐Hydr­oxy‐6‐[(2‐hydroxy­phenyl­amino)methyl­ene]cyclo­hexa­‐2,4‐dienone
B. Koşar (2005)
10.1016/0022-1902(69)80121-1
NN′ ethylene bis (salicylideneimine) complexes of manganese (III) halides
C. P. Prabhakaran (1969)
10.1039/B106145N
Low barrier hydrogen bonds in sterically modified Schiff bases
A. Filarowski (2002)
10.1016/j.saa.2013.05.044
The prototropic tautomerism and substituent effect through strong electron-withdrawing group in (E)-5-(diethylamino)-2-[(3-nitrophenylimino)methyl]phenol.
Ç. Albayrak (2013)
10.1063/1.438955
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions
R. Krishnan (1980)
ANTIOXIDANT ACTIVITY OF MELISSA OFFICINALIS LEAVES
E. Köksal (2011)
10.3109/10715769709084484
Antioxidant activities of some extracts of Thymus zygis.
J. Soares (1997)
Gaussian 03, Revision E.01.
M. Frisch (2007)
10.1016/S0891-5849(98)00315-3
Antioxidant activity applying an improved ABTS radical cation decolorization assay.
R. Re (1999)
10.1016/J.MOLSTRUC.2011.06.018
Probing the compound (E)-2-[(4-bromophenylimino)methyl]-6-ethoxyphenol mainly from the point of tautomerism in solvent media and the solid state by experimental and computational methods
Çiǧdem Albayrak (2011)
10.1107/S0021889899006020
WinGX suite for small-molecule single-crystal crystallography
L. Farrugia (1999)
10.1021/ci00011a011
Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of .pi.-electron systems
T. Krygowski (1993)
10.1016/J.PNMRS.2006.07.001
The use of NMR spectroscopy to study tautomerism
R. M. Claramunt (2006)
10.1063/1.475855
Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold
M. E. Casida (1998)
10.1038/1811199a0
Antioxidant Determinations by the Use of a Stable Free Radical
M. Blois (1958)
10.1103/PhysRevLett.52.997
Density-Functional Theory for Time-Dependent Systems
Erich Runge (1984)
10.1016/0143-7208(94)85012-7
Metal complex dyes of nickel with schiff bases
S. Papić (1994)
10.1021/j100785a001
van der Waals Volumes and Radii
A. Bondi (1964)
10.22037/IJPR.2012.1159
Evaluation of in-vitro Antioxidant Properties of Hydroalcoholic Solution Extracts Urtica dioica L., Malva neglecta Wallr. and Their Mixture
A. Güder (2012)
10.1016/j.saa.2012.04.074
Survey of conformational isomerism in (E)-2-[(4-bromophenylimino)methyl]-5-(diethylamino)phenol compound from structural and thermochemical points of view.
Çiğdem Albayrak (2012)
10.1016/0022-1902(80)80005-4
Cobalt(II), nickel(II), copper(II), thorium(IV) and uranium(VI) complexes of some heterocyclic Schiff bases derived from hydroxy aromatic aldehydes and 2-aminopyridine
M. Mahmoud (1980)
10.1016/S0040-4020(01)90255-8
Photochromism and thermochromism of Schiff bases in the solid state and in rigid glasses
E. Hadjoudis (1987)
10.1016/S0040-4039(01)94175-9
Definition of aromaticity basing on the harmonic oscillator model
J. Kruszewski (1972)
10.1007/S11243-005-4826-4
Spectral, physicochemical and biological characterization of 2,5,11,14,19,20-hexaaza-3,12-dimethyl-4,13-dipropyl-tricyclo [13.3.1.1(6-10)]cosane-1(19),2,4,6(20),7,9,11,13,15,17-decaene and its transition metal complexes
S. Chandra (2005)
10.1016/0022-2860(88)80087-5
Hydrogen bond studies in thermochromic and photochromic N-salicylidene anilines
F. Milia (1988)
10.1016/0009-2614(96)00440-X
TREATMENT OF ELECTRONIC EXCITATIONS WITHIN THE ADIABATIC APPROXIMATION OF TIME DEPENDENT DENSITY FUNCTIONAL THEORY
R. Bauernschmitt (1996)
10.1016/J.MOLSTRUC.2012.03.005
Investigating the prototropic tautomerism in (E)-2-[(4-fluorophenyl)iminomethyl]-5-methoxyphenol compound for solid state and solvent media by experimental and quantum computational tools
G. Kaştaş (2012)
10.1016/j.saa.2015.07.030
Analysis of tautomeric equilibrium in (E)-4,6-dibromo-2-[(4-fluorophenylimino)methyl]-3-methoxyphenol compound.
Çiğdem Albayrak Kaştaş (2015)
10.1007/S11224-010-9598-6
The proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol
H. Petek (2010)
10.1021/JF980496S
Method for measuring antioxidant activity and its application to monitoring the antioxidant capacity of wines.
V. Fogliano (1999)



This paper is referenced by
10.1016/J.MOLSTRUC.2018.11.005
Structural, spectroscopic, radical scavenging activity, molecular docking and DFT studies of a synthesized Schiff base compound
Halil İbrahim Gökce (2019)
10.1007/s10661-018-6829-6
A comparison of the antioxidant activities and biomonitoring of heavy metals by pollen in the urban environments
İlginç Kızılpınar Temizer (2018)
10.1016/J.MOLSTRUC.2019.02.058
Scrutinizing the two new o-hydroxy Schiff bases from the point of tautomeric behavior and non-covalent interactions (H-bond, Br⋯Br, π⋯π and CH⋯π) in their supramolecular architectures
Gökhan Kaştaş (2019)
10.1002/JHET.3135
Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives
M. S. Kazunin (2018)
10.30516/BILGESCI.393717
Infrared and NMR Spectral Analyses and Computational Studies of 2-amino-3-methylbenzoic acid
Muhammet Yildirim (2018)
10.20450/MJCCE.2019.1531
Dependence of tautomerism on substituent type in o-hydroxy Schiff bases
Ç. A. Kaştaş (2019)
10.1007/s00706-017-2137-z
Synthesis and antiradical activity of novel copper(II) complexes of long chain reduced Schiff base ligands
Lucia Lintnerová (2018)
10.1016/j.molstruc.2019.127109
The effect of the change in substituents’ positions on the formation of supramolecular networks and the solvent type/substituent dependence of prototropic behavior in three new o-hydroxy Schiff bases
Gökhan Kaştaş (2020)
10.1016/j.saa.2019.117198
Investigation of molecular structure and solvent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV-vis, NMR and DFT methods.
Gökhan Kaştaş (2019)
( II ) , Zn ( II ) , Ru ( II ) , Pd ( II ) Kompleksleri : Sentez , Karakterizasyon ve
Katalitik Çalışmalar (2019)
Semantic Scholar Logo Some data provided by SemanticScholar