64174-57-8

Basic information

• Product Name: N^'1,N^'4-bis(2-hydroxybenzylidene)succinohydrazide
• Synonyms: N^'1,N^'4-bis(2-hydroxybenzylidene)succinohydrazide
• CAS NO: 64174-57-8
• Molecular Weight: 354.365
• Mol File: 64174-57-8.mol

Chemical Properties

• CAS DataBase Reference: N^'1,N^'4-bis(2-hydroxybenzylidene)succinohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: N^'1,N^'4-bis(2-hydroxybenzylidene)succinohydrazide(64174-57-8)
• EPA Substance Registry System: N^'1,N^'4-bis(2-hydroxybenzylidene)succinohydrazide(64174-57-8)

Safety Data

• Hazardous Substances Data: 64174-57-8(Hazardous Substances Data)

Upstream product

• 4146-43-4 succinic acid dihydrazide 
• 90-02-8 salicylaldehyde 
• 123-25-1 succinic acid diethyl ester 

Relevant articles and documents

A family of Fe3+ based double-stranded helicates showing a magnetocaloric effect, and Rhodamine B dye and DNA binding activities

Herein, the synthesis, structural characterization, magnetic properties and guest binding activities of four Fe3+ based double-stranded helicates namely; [Fe2(L)2](ClO4)(Cl)·4(CH3OH)·2(H2O) (1), [Fe2(L)2](BF4)2·2(H2O) (2), [Fe2(L)2](NO3)2·3(CH3OH)·2(H2O) (3), and [Fe2(L)2](Cl)2·2(CH3OH)·4(H2O) (4) are reported. Complexes 1-4 have been synthesized using the hydrazide-based ligand H2L (H2L = N′1,N′4-bis(2-hydroxybenzylidene)succinohydrazide) and the corresponding Fe2+ salts. Each of the independent cationic complexes [Fe2(L)2]2+ shows double-stranded helicates from the self-assembly of the ligand and metal ions in a 2 : 2 ratio, where the individual Fe3+ centre is lying on a C2-axis and the ligand strands wrap around it. In 1-4, ligand L adopts pseudo-C conformations and forms a double-stranded dinuclear helicate with a small cage in between them. Moreover, in 1-4, each of the independent cationic complexes [Fe2L2]2+ is inherently chiral and possesses P for right-hand and M for left-hand helicity and as a consequence is a racemic solid. Detailed magnetic studies of all the complexes reveal that the Fe3+ centres are magnetically isolated and isotropic in nature. Estimation of the Magnetocaloric Effect (MCE) from magnetization data unveils a moderate MCE at a temperature of 3 K with magnetic entropy changes (-ΔSm) of 22.9, 27.7, 24.1, 26.5 J kg-1 K-1 at a magnetic field of 7 T for complexes 1-4, respectively. Also, the variation of the -ΔSm values was justified by considering the parameter of magnetization per unit mass. Stability of all the complexes in solution phase was confirmed by ESI-mass spectrometric analysis and liquid phase FT-IR spectroscopy. Further, the interaction of the complexes 1-4 with Rhodamine B dye was examined by UV-vis and fluorescence spectroscopic study. The observed blue-shift in the fluorescence study and hyperchromicity and hypochromicity with the appearance of two isosbestic points in the UV-vis study ascertain the interactions of the dye with the complexes. A DNA binding study by absorption spectral titration suggests the weak external intercalation of complex 1 within the nucleotide of calf thymus DNA. Computational study supports the isotropic nature of the metal centres and the consequent high spin multiplicity, which assists the complexes to show significant magnetic entropy changes.

Synthesis, Characterization, and Fluorescence Chemosensor Properties of a cis-Dioxomolybdenum(VI) Complex Containing Multidentate Hydrazone Ligands

The homobimetallic molybdenum(VI) complex, [(MoO2)2(slsch)(DMF)2], derived from multidentate hydrazone ligand (H4slsch = disalicylaldehyde succinoyldihydrazone) was synthesized. The complex was obtained by reaction of the ligand with Mo2(acac)2 in 1:2 molar ratio in methanol. It was characterized by using various spectroscopic techniques. The structure of the complex was established by single crystal X-ray diffraction. The complex shows fluorescence emission, responds toward AlIII ions, and hence it can be used as fluorescence chemosensor for sensing AlIII ions. The sensing properties show that the complex is more efficient and sensitive towards AlIII ions than the rest of the ions used in the presented study.

Synthesis, structure, magnetic and biological activity studies of bis-hydrazone derived Cu(II) and Co(II) coordination compounds

Four coordination compounds of formulae [CuII2(H2L1)(HL1)](ClO4)3·H2O (1), [CuII2(H2L2)(CH3OH)2](ClO4)2·2CH3OH (2), [CoII2(H2L1)2](ClO4)4 (3) and [CoII2(H2L2)2]·2H2O (4) were synthesized via self-assembly of succinohydrazone derived ligands (H2L1 = N′,N′-4-bis(2-pyridyl)succinohydrazide, H4L2 = N′,N′-4-bis(2-hydroxybenzylidene)succinohydrazide) and Cu2+ and Co2+ ions, respectively. The compounds were characterized by crystal structure determination, magnetic measurements and biological activities. Compounds 1, 3 and 4 have discrete double helicate structures, whereas compound 2 is a one-dimensional chain. Magnetic studies show antiferromagnetic exchange interactions in 2 with a J value of -67.1 cm-1 and antiferromagnetic spin-canting in compound 3 originates through supramolecular H-bonding. For compound 3, a clear bifurcation was observed in zero field cooled (ZFC) and field cooled (FC) measurement at a temperature of 3.5 K and field of 0.1 T, implying long range magnetic ordering below this temperature. Interestingly, all of compounds 1-4 show significant changes in their absorption (hypo- and hyperchromism) in the presence of SS-DNA, inferring interaction between the compounds and DNA. In addition, compounds 1-4 significantly exhibited nuclease activities on both RNA and pUC19 plasmid DNA. Moreover, the nuclease activity was further enhanced in the presence of oxidant (H2O2) and suggests the possible role of reactive oxygen species in DNA nicking ability of compounds 1-4. Furthermore, compounds 1, 2 and 4 exhibited significant cytotoxicity against mammalian cancer cell lines (HeLa, A549 and MDAMB-231). In addition, our results from Annexin/PI staining and DNA fragmentation assays revealed that these compounds are capable of inducing apoptosis and have potential to act as anticancer drugs.

Homobimetallic organotin(IV) complexes with succinohydrazide Schiff base: Synthesis, spectroscopic characterization, and biological screening

Six new bis-diorganotin(IV) complexes, [(Me2Sn)2L] (1), [(Et2Sn)2L] (2), [(n-Bu2Sn)2L] (3), [(Ph2Sn)2L] (4), [(n-Oct2Sn)2L] (5), and [(tert-Csub

A new dihydrazone based turn on fluorescent sensor for Zn(II) ion in aqueous medium

A new simple dihydrazone based colorimetric and fluorescent turn-on chemosensor (disalicyladehyde succinoyldihydrazone, I) for Zn(II) was designed and synthesized. The photophysical behavior of the ligand and metal coordinated complex was characterized by steady state and time-resolved fluorescence, density functional theory calculation in combination with 1H NMR and mass spectroscopy results. The compound acts as a highly selective and sensitive detector of Zn(II) in aqueous medium with almost six times increase in fluorescence intensity. The optimum condition for sensing ability of I with a detection limit of ca. 2 μM of Zn(II) was found at solution pH 8.6 and at excitation wavelength of 380 nm. The other interfering elements, including Cd(II), show either no or very little change in fluorescence intensity under similar experimental conditions.

The fabrication and characterization of a supramolecular Cu-based metallogel thin-film based Schottky diode

In the present study, a stable supramolecular Cu(ii)-metallogel has been synthesized based on copper(ii) acetate monohydrate and succinic acid, engineered as a low-molecular-weight organic gelator. The mechanical assets of the Cu-H4L metallogel have been explored through a rheological investigation. Further, the aggregation of the synthesized metallogel has been well establishedviaseveral experiments using Job plots and ESI-MS. Apart from this, the morphology of the synthesized supramolecular metallogel was scrutinizedviaFESEM, TEM, and AFM studies, revealing the self-assembled thread-like morphology of the Cu-H4L metallogel. The functional group, elemental composition, crystalline behaviour, and thermal stability of the Cu-H4L metallogel were probedviaFT-IR, XPS, P-XRD, and TGA studies, respectively. The optical properties of the Cu-H4L metallogel reflected its semiconducting nature. Thus, based on the semiconducting properties of the Cu-H4L metallogel, we have successfully fabricated an active electronic device: a ‘Schottky diode’.

Synthesis, characterization, crystal structure, and reactivity of heterobimetallic dioxovanadium(V) complexes containing multidentate hydrazone ligands

Two new heterobimetallic complexes of the composition [(VO2)2(μ3-slsch){Na2(μ-H2O)2(H2O)2}]n (1) and [(VO2)2(μ3-npsch){Na2(μ-H2O)2(H2O)2}(DMF)]n (2) were obtained by reaction of the ligand and vanadium pentoxide in a 1:1 molar ratio in methanol in the presence of Na2CO3 (2 equivalents). The complexes obtained were characterized using various spectroscopic studies. The structures of both the complexes were established by single crystal X-ray crystallographic study. We have also explored the catalytic behavior of the complexes in oxidative bromination of phenol red, which is the bio-inspired reaction catalyzed by an enzyme haloperoxidase.

Synthesis and characterization of heterotrinuclear bis(μ2- chlorido)dicopper (II) mono zinc(II) complexes derived from succinoyldihydrazones

Three new zinc (II)-copper (II) heterometallic trinuclear complexes of the composition [ZnCu2(Ln)(μ2-Cl) 2(H2O)6]×2H2O (H 4Ln = H4L1, H4L 2, H4L3) have been synthesized from substituted succinoyldihydrazones (H4Ln) in methanol medium. The composition of the complexes has been established on the basis of data obtained from analytical, mass spectral studies and molecular weight determinations in DMSO. The structure of the ligand H4L2 has been established by X-ray crystallography. The structure of the complexes has been discussed in the light of molar conductance, magnetic moment, electronic, EPR, IR and FT-IR spectral studies. The molar conductance values for the complexes fall in the region 1.2-1.7 ohm-1 cm2 mol-1 in DMSO solution indicating that all of these are non-electrolyte. The magnetic moment values suggest weak M-M interaction in the structural unit of the complexes. The dihydrazone ligand is present in enol form in all of the complexes. Copper centre has tetragonally distorted octahedral stereochemistry. The EPR parameters of the complexes indicate that the copper centre has doublet state as the ground state. The electron transfer reactions of the complexes have been investigated by cyclic voltammetry.

Synthesis, characterization and electrochemical properties of bis(μ2-perchlorato)tricopper(ii) complexes derived from succinoyldihydrazones

Three new homotrimetallic copper(ii) complexes ([Cu3(L n)(ClO4)2(H2O)m] with H4Ln = H4L1 - H4L 3, m = 0, 3) have been synthesized from substituted succinoyldihydrazones (H4Ln) in methanol. The composition of the complexes has been established on the basis of data obtained from analytical and mass spectral studies and molecular weight determination in DMSO. The structure of the complexes has been discussed in the light of molar conductance, magnetic moment data and electronic, EPR, IR and FT-IR spectral studies. The molar conductance values for the complexes in the region of 1.2-1.7 Ω-1 cm2 mol-1 in DMSO indicate that the complexes are nonelectrolytes. The magnetic moment values for the complexes suggest considerable metal-metal interaction in the structural unit of the complexes. Copper centres have square planar and square pyramidal stereochemistry. The EPR parameters of complexes 1 and 3 indicate that the copper centre has a doublet ground state, while for complex 2, the ground state is a mixture of both doublet and quartet states. Electron transfer reactions of the complexes have been investigated by cyclic voltammetry. The Royal Society of Chemistry 2013.

Synthesis, spectroscopic and electrochemical characterisation of binuclear dioxomolybdenum complexes derived from disalicylaldehyde succinoyldihydrazone

The diamagnetic dioxomolybdenum (VI) complexes [(MoO2) 2(L).(H2O)2] where H4L = H 4slsh have been isolated in solid state from the reaction of MoO 2(acac)2 and disalicylaldehyde succinoyldihydrazone (H4L) in 3:1 molar ratio in ethanol at higher temperature. The reaction of the complex with electron donor bases gives diamagnetic molybdenum(VI) complexes having composition [(MoO2) 2(L)(A)2]·H2O (where A = pyridine (py, 2), 2-picoline (2-pic, 3), 3-picoline (3-pic, 4), 4-picoline (4-pic, 5). The composition of the complexes have been established by analytical, thermo-analytical data. The structure of the molybdenum (VI) complexes has been established by mass, electronic, IR, 1H NMR and CV spectral studies. The dihydrazone is coordinated to the metal centres in staggered configuration in all the complexes. The electronic spectra of the complexes are dominated by strong charge transfer bands. All of the complexes involve six coordinated molybdenum centre with octahedral arrangement of donor atoms.