3-nitrophthalic Acid Research Articles

Very Strong Hydrogen Bond in Nitrophthalic Cocrystals.

This work presents the studies of a very strong hydrogen bond (VSHB) in biologically active phthalic acids. Research on VSHB comes topical due to its participation in many biological processes. The studies cover the modelling of intermolecular interactions and phthalic acids with 2,4,6-collidine and N,N-dimethyl-4-pyridinamine complexes with aim to obtain a VSHB. The four synthesized complexes were studied by experimental X-ray, IR, and Raman methods, as well as theoretical Car-Parrinello Molecular Dynamics (CP-MD) and Density Functional Theory (DFT) simulations. By variation of the steric repulsion and basicity of the complex' components, a very short intramolecular hydrogen bond was achieved. The potential energy curves calculated by the DFT method were characterized by a low barrier (0.7 and 0.9 kcal/mol) on proton transfer in the OHN intermolecular hydrogen bond for 3-nitrophthalic acid with either 2,4,6-collidine or N,N-dimethyl-4-pyridinamine cocrystals. Moreover, the CP-MD simulations exposed very strong bridging proton dynamics in the intermolecular hydrogen bonds. The accomplished crystallographic and spectroscopic studies indicate that the OHO intramolecular hydrogen bond in 4-nitrophthalic cocrystals is VSHB. The influence of a strong steric effect on the geometry of the studied cocrystals and the stretching vibration bands of the carboxyl and carboxylate groups was elaborated.

Improving the Solubility and Bioavailability of Progesterone Cocrystals with Selected Carboxylic Acids.

Progesterone (PROG) is a natural steroid hormone with low solubility and high permeability that belongs to biopharmaceutics classification system class II. In this study, novel pharmaceutical cocrystals of PROG were successfully prepared by solvent evaporation or a liquid-assisted grinding process aimed at enhancing its solubility and bioavailability. The cocrystal formers selected based on crystal engineering principles were carboxylic acids, namely, 4-formylbenzeneboronic acid (BBA), isophthalic acid (IPA), and 3-nitrophthalic acid (NPA). The cocrystal structures were characterized using multiple techniques. Single-crystal X-ray diffraction results showed that the carbonyl group, acting as a hydrogen bond acceptor, was pivotal in the cocrystal network formation, with C-H···O interactions further stabilizing the crystals. The cocrystals exhibited improved solubility and dissolution profiles in vitro, with no significant changes in hygroscopicity. The parallel artificial membrane permeability assay (PAMPA) models indicated that the cocrystals retained PROG's high permeability. Pharmacokinetic studies in Sprague-Dawley rats revealed that all cocrystals increased PROG exposure, with AUC(0~∞) values for PROG-BBA, PROG-IPA, and PROG-NPA being 742.59, 1201.72 and 442.67 h·ng·mL-1, respectively. These values are substantially higher compared to free PROG, which had an AUC(0~∞) of 301.48 h·ng·mL-1. Notably, PROG-IPA provided the highest AUC improvement, indicating a significant enhancement in bioavailability. Collectively, the study concludes that the cocrystal approach is a valuable strategy for optimizing the physicochemical properties and oral bioavailability of PROG, with potential implications for the development of other poor water-soluble drugs.

Preparation, crystallographic feature, synthon investigation and Hirshfeld surface analysis of both 3D supramolecular anhydrous organic salts constructed by triphenylmethylamine, 3-nitrophthalic acid and 5-nitroisophthalic acid

Preparation, crystallographic feature, synthon investigation and Hirshfeld surface analysis of both 3D supramolecular anhydrous organic salts constructed by triphenylmethylamine, 3-nitrophthalic acid and 5-nitroisophthalic acid

Hydrogenation of 3-Nitrophthalic Acid on Palladium-Containing Nanocomposite Catalysts

Hydrogenation of 3-Nitrophthalic Acid on Palladium-Containing Nanocomposite Catalysts

Synthesis, crystal growth and characterization of organic 1,2,4-triazole p-nitrophthalic acid (TPNP) single crystal for nonlinear optical (NLO) applications

The novel organic NLO single crystal 1,2,4-Triazole 4-nitrophthalic acid (TPNP) has been synthesised with methanol as a solvent in an equimolar ratio (1:1) by slow evaporation solution technique (SEST). The grown material was characterized for its NLO applications and reported for the first time. TPNP single crystal with the dimension of 10 mm × 5 mm × 4 mm was grown. The grown crystal was analysed through various characterization studies such as structural, optical, thermal, electrical and third harmonic generation (Z-scan) studies. The structural confirmation of the grown TPNP crystals was investigated by Single Crystal X-ray diffraction (SXRD) analysis. The Powder X-ray diffraction (PXRD) was used to identify the (h k l) planes for the purpose of drawing the morphology diagram of the original crystal image. The optical analysis carried out using UV–Vis-NIR study on TPNP crystal showed good optical transparency (80 %) and it can be used for various optical applications. To identify the structure and the functional groups, Fourier transform infrared (FTIR) study was conducted. Thermogravimetric and differential thermal analysis (TG-DTA) revealed the thermal stability of the grown TPNP crystal upto 155 °C. The surface etch pit density of TPNP crystal was carried out using chemical etching analysis. The negative photoconductive nature of title crystal was identified by photoconductivity analysis. The dielectric permittivity and dielectric loss as a function of frequency were measured for grown crystal. Intermolecular interactions and fingerprint plots of TPNP molecules are executed by Hirshfeld surface analysis. LDT of the title crystal was investigated by Q-switched Nd: YAG laser of wavelength 532 nm. Third order NLO parameters and susceptibility were determined using the Z-scan technique. It is concluded that the material can be effectively employed for various optoelectronic and photonic applications.

Estimating the anti-corrosive potency of 3-nitrophthalic acid as a novel and natural organic inhibitor on corrosion monitoring of mild steel in 1 M HCl solution

Application of inhibitors is the most practical technique for protection of metals against corrosion in harsh solutions. But, the environmental worries and the carcinogenic impact have caused some traditional inhibitors to be banned by several international agencies. So, remarkable attention has been directed to the natural compounds. This project aimed to introduce a natural organic compound named 3-nitrophthalic acid as a novel corrosion inhibitor for enhancement of steel structure lifetime against corrosion in an acidic medium. Electrochemical measurements were done for this purpose. Fourier Transform Infrared (FT-IR) and UV–Visible spectroscopies were applied to characterize chemical structure of the inhibitor. Electrochemical impedance spectroscopy (EIS) manifested the maximum inhibition performance of about 80.51 % for the sample containing 400 ppm 3-nitrophthalic acid. Potentiodynamic polarization outcomes exhibited reduction of both anodic and cathodic reactions rate in the presence of inhibitor through a mixed inhibition mechanism. Besides, surface examinations including scanning electron microscopy (SEM), atomic force microscopy (AFM), and contact angle (CA) confirmed the anticorrosive behavior of 3-nitrophthalic acid via surface smoothness and the creation of a hydrophobic film arising from inhibitor adsorption on the mild steel surface, which obeyed the Langmuir adsorption model.

Two new zinc(II) coordination polymers containing bis(thiabendazole) ligands for fluorescence detection of Fe3+ ions and norfloxacin/ornidazole

Two new functionalized coordination polymers (CPs), namely, [Zn2L(NDC)2(H2O)]n (1) and {[ZnL(NPTA)(H2O)]·H2O}n (2) (H2NDC = 1,4-naphthalenedicarboxylic acid, H2NPTA = 3-nitrophthalic acid) based on semi-rigidity 1,4-bis(thiabendazol-1-yl)-2-butene (L) N-donor linker are synthesized by a hydrothermal method. Two CPs are 2D 63-hcb layer and 1D chain, respectively. 1 reveals a 2D hcb sheet with the point symbol of {63}. 2 displays a 1D chain. 1 and 2 can serve as dual luminescent probes to sense Fe3+ and norfloxacin/ ornidazole with low detection limits. The luminescent sensing mechanism of the two CPs was investigated in detail.

Exploring the cutting-edge properties of 3-nitrophthalic acid single crystal: growth, structure, optical and quantum chemical studies

Exploring the cutting-edge properties of 3-nitrophthalic acid single crystal: growth, structure, optical and quantum chemical studies

Synthesis, crystal structures and DNA-binding properties of Zn(II), Cd(II), Mn(II), Cu(II) complexes based on a thiazole derivative and carboxylic acids

By single-crystal X-ray diffraction (XRD) analysis, five complexes, catena-[(µ-2,2-bis(4-carboxyphenyl)hexafluoropropane)-(2-(pyidin-2-yl)-1,3-benzothiazole)-aqua-zinc(II)] (1), catena-[(µ-2,2-bis(4-carboxyphenyl)hexafluoropropane)-(2-(pyidin-2-yl)1,3-benzothiazole)-aqua-cadmium(II)] (2), catena-[hepta(µ-2,2-bis(4carboxyphenyl)hexafluoropropane)-diaqua-bis(2-(pyidin-2-yl)-1,3-benzothiazole)-tri-manganes(II)] (3), catena-[(µ-benzene-1,2,4,5-tetracarboxylato)-(2-(pyidin-2-yl)-1,3benzothiazole)copper(II)] (4) and catena-[(µ-3-nitrobenzene-1,2-dicarboxylato)-(2-(pyidin-2-yl)1,3-benzothiazole)-aqua-zinc(II)] (5), were characterized in this research. In these five complexes, H2hfipbb = 2,2-bis(4-carboxyphenyl)hexafluoropropane, H4btec = 1,2,4,5-benzenetetracarboxylic acid, H2NPTA = 3-nitrophthalic acid and bpt = 2-(pyridin-2-yl)benzo[d]thiazole). Complexes 1 and 2 occur in the monoclinic system with space group C2/c, 4 and 5 occur in the monoclinic system with space group P21/c, and 3 occurs in the triclinic system with space group P-1. The interaction between CT-DNA (calf thymus DNA) and those complexes was examined using UV spectroscopic analysis, fluorescent spectroscopic analysis, circular dichroism spectroscopy (CD) and viscosity analysis. This research reveals that those complexes have strong ability to interact with DNA, and they all bind to DNA in an intercalation mode, thus affecting the structure of DNA. This binding mode can arise from the interaction between the benzothiazole metal complexes and DNA. Hence, we hope to provide some scientific research bases for studying benzothiazole complexes and designing new thiazole anticancer drugs.

Two Zn(II)-based coordination polymers as dual-responsive luminescent sensors for the detection of Cr2O72− ions, levofloxacin/sulfamethoxazole

Two Zn(II) coordination polymers (CPs), [Zn(NBTA)(HL)] n ( 1 ) and {[Zn(4-NPA)(L)]·H 2 O} n ( 2 ) were hydrothermally synthesized. 1 and 2 can selectively detect Cr 2 O 7 2− /levofloxacin, and Cr 2 O 7 2− /sulfamethoxazole with high selectivity, low detection limits and excellent reusability, respectively, via the luminescence quenching process. • Two new coordination polymers were synthesized and characterized. • 1 and 2 exhibited highly sensitive and selective detecting abilities for Cr 2 O 7 2− ions. • 1 could treat as an efficient probe for the sensing of levofloxacin. • 2 could detect sulfamethoxazole with high sensitivity. Two new ternary coordination polymers (CPs), namely, [Zn(NBTA)(HL)] n ( 1 ) and {[Zn(4-NPA)(L)]·H 2 O} n ( 2 ) (H 3 NBTA = 5-nitro-1,2,3-benzenetricarboxylic acid, 4-H 2 NPA = 4-nitrophthalic acid, L = 1,4-bis(benzimidazol-2-yl)butane were hydrothermally synthesized and characterized. 1 possesses a 1D straight chain, which is further extended into a 2D supramolecular network through π–π stacking interactions. 2 exhibits the 2D hcb layer. The two CPs present highly thermal and chemical stabilities in the pH range from 3 to 12. 1 and 2 can selectively detect Cr 2 O 7 2− ions/levofloxacin, and Cr 2 O 7 2− ions/sulfamethoxazole, respectively, with recyclability and low detection limits.

SYNTHESIS, SPECTRAL AND MAGNETIC SUSCEPTIBILITY STUDIES OF 1,8,15,22- TETRAIODOPHTHALOCYANINE COMPLEXES OF COBALT, NICKEL, COPPER AND ZINC

Some 1,8,15,22-tetraiodophthalocyanine complexes of cobalt (3-ICoPc), nickel (3-INiPc), copper (3-ICuPc) and zinc (3- IZnPc) were synthesized from the corresponding tetraamino substituted metal phthalocyanine complexes using modified Sandmayer’s method. The corresponding 1,8,15,22-tetranitrophthalocyanine complexes of the metals were used as precursors for the synthesis of 1,8,15,22-tetraamino substituted metal phthalocyanines. 1,8,15,22- tetranitrophthalocyanine complexes were in turn synthesized from reaction between 3-nitrophthalic acid with corresponding metal salts. The characterization of bluish green colored complexes was done by elemental analyses, Uvvisible and IR spectroscopy, and magnetic susceptibility measurements in order to check their purity and structural integrity. Measurement of magnetic susceptibility with varying magnetic field strengths revealed that, the magnetic moments are higher than the spin only values and shows the presence of intermolecular cooperative effects.

BIODEGRADATION OF HIGH MOLECULAR WEIGHT POLYCYCLICAROMATIC HYDROCARBON CHRYSENE BY SOIL BACTERIALISOLATES

PAHs (polycyclic aromatic hydrocarbons) are common and dangerous organic pollutants made primarily of carbon and hydrogen. Chrysene is also a potential human carcinogen and a high molecular weight PAH. The current research focuses on chrysene biodegradation, and effective chrysene degrading microbial strains were identified from soil samples taken from the hydrocarbon-contaminated surrounding soil of the Mathura petroleum refinery in Uttar Pradesh, India. The isolated isolates were morphologically examined, and basic biochemical tests were performed. 16sRNA analysis was performed for molecular analysis, and it was discovered that 3AS belongs to Enterobacter sp. and 5AS belongs to Ochrobactrum sp. The biodegradation efficiency of strain 3AS was 60%, while strain 5AS could only digest 55% of chrysene in MSM (Minimal Salt Media). The principal metabolite of chrysene biodegradation discovered in the cultures of strain3AS using the GC-MS (Gas chromatography-mass spectrophotometry) technique, as well assignificant metabolites such as phenol, 2, 5-bis (1,1- dimethyl ethyl), 1-naphthoic acid, 8-methoxy,and 3-nitrophthalic acid. In 5AS cultures, phthalic acid and di-isobutyl ester was detected. Thecatechol-1, 2-dioxygenase gene was not found, but the presence of catechol-2, 3-dioxygenasesuggests that chrysene can be degraded via the meta cleavage pathway.

Two dual-responsive luminescent coordination polymers for highly effective sensing of enrofloxacin and Al3+ ions

Highly sensitive and selective fluorescence sensing of antibiotics and heavy metal ions are extremely vital to safeguard human health. Two new water-stable ternary coordination polymers (CPs), {[Cd(NPTA)(L)]·1.75H2O}n (1) and [Co1.5(BTC)(L)]n (2) (H2NPTA = 3-nitrophthalic acid, H3BTC = 1,3,5-benzenetricarboxylic acid, and L = 1,5-bis(benzimidazole-2-yl)pentane) were prepared through the hydrothermal process. 1 features a 1D zigzag infinite chain which is linked into a 2D network via π–π stacking interactions, while 2 shows a 2D 3,4L35 layer and can be further extended into a 3D supramolecular framework by hydrogen-bonding interactions. The two CPs display superior thermal and chemical stability in a wide pH range from 3 to 12. Furthermore, both 1 and 2 can be as the dual-responsive probes for selective sensing of enrofloxacin (ENR) and Al3+ ions with reusability.

Hydrogen bonding interactions on molecular properties of pesticidal compound 4-nitrophthalic acid: experimental density functional theory computations, electron localized function, localized orbital locator analysis and molecular docking scrutiny

Nitroaromatic compounds are expansively used in the manufacturing of pharmaceuticals, pesticides, plasticizers, azo dyes and explosives. Nitrophenolic compounds can accumulate in the soil as a result of hydrolysis of several insecticides such asparathion, methyl parathion, and fenitrothion which can cause propitious effects to the biological systems. In optimized geometry hyperconjugation of nitro and dicarboxylic acid groups with the ring system increases the electron density of the aromatic system. Electron localized Function and Localized orbital Locator Analysis has value in a region wherein indicates high localization of electrons due to the presence of covalent bond, a lone pair of electrons or a nuclear shell in that region. In Nuclear Magnetic Resonance analysis signals in highly deshielded region clearly indicates the presence of carboxylic carbon in the compound. From vibrational assignments, broadening and red shifting depicts the level of intermolecular hydrogen bonding. In-vitro antimicrobial activity results clearly reveal that in all the four strains, activity increases with increase in compound concentration and the inhibition of the strains also increases. From both molecular docking and In-vitro Antimicrobial Activity the title compound can be certified that it inhibits antimicrobial activity and it is a pesticide.

Syntheses, structures and fluorescence properties of a Zn and a Cd(II) coordination polymer based on the mixed ligands

Two new compounds, [Zn(4-npa)(btmb)]n (1) and [Cd(4-npa)(btmb)0.5(H2O)2]n (2) (H24-npa = 4-nitrophthalic acid, btmb = 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene) have been achieved under hydrothermal conditions and structurally characterized by elemental analysis, IR spectroscopy and single-crystal x-ray diffraction. The compound 1 crystallizes in monoclinic crystal system, space group P21/c and is characterized by a two-dimensional layer structure containing 1 D Zn-carboxylate chains. Wherein the central Zn(II) ion is coordinated by two carboxylate O atoms and two N atoms to give a distorted tetrahedral [ZnO2N2] geometry. In compound 2, The hexa-coordinated Cd(II) ion forms a slightly distorted octahedral [CdNO5] geometry. The two Cd(II) centers are bridged by pair 4-npa dianions adopting bidentate-bridging mode to form a dinuclear unit. The dinuclear units are linked together by 4-npa dianions to form a Cd-carboxylate layer, and further extend by btmb molecules to form a 3 D pillared-layer metal–organic framework. The thermogravimetric analyses and luminescent properties of two compounds are also investigated.

Structural characterization of sodium and potassium 3-nitrohydrogenphthalate coordination polymers

Abstract The synthesis, crystal structures and properties of two alkali metal 3-nitrohydrogenphthalates obtained by a 1:2 reaction of M2CO3 (M = K or Na) with 3-nitrophthalic acid (LH2) are reported. In the anhydrous potassium coordination polymer [K(LH)] (LH = 2-carboxy-3-nitrobenzoate) 1, the K+ cation is bonded to nine oxygen atoms from six symmetry related (LH)– ligands resulting in a distorted {KO9} coordination polyhedron. Five of the six oxygen atoms including a nitro oxygen atom of the crystallographically unique 2-carboxy-3-nitrobenzoate are involved in metal binding. The μ6-bridging mode of (LH)– places the K+ cations into the layers of the two-dimensional (2D) coordination polymer. Each {KO9} polyhedron in 1 shares edges with two other polyhedra along the b and c axes. A low temperature structure redetermination of [Na(L#H)(H2O)3]·H2O (L#H = 2-carboxy-6-nitrobenzoate) 2 has revealed that the (L#H)− anion is bonded to the Na+ cation in a monodentate fashion via the carbonyl oxygen atom of the –COOH group and two of the three unique aqua ligands exhibit a bridging bidentate mode stabilizing a chain polymer. The structure of compound 2 thus consists of chains of edge-sharing {NaO6} octahedra. Thermal decomposition of 1 or 2 results in the formation of metal carbonate residues.

Formation of secondary organic aerosol tracers from anthropogenic and biogenic volatile organic compounds under varied NO and oxidant conditions

For source apportionment by tracer method of secondary organic aerosol (SOA), the ratios of aerosol tracer to total SOA mass ( f SOA ) were determined during the oxidation of toluene, naphthalene, α-pinene, and isoprene by a series of laboratory experiments. Seven anthropogenic SOA tracers maintaining an aromatic ring structure, including 4-nitrophthalic acid and 3,5-dinitrosalicylic, were newly investigated as a chamber study together with 21 traditional aerosol tracers of anthropogenic and biogenic SOA. Experiments of the OH-initiated oxidation of anthropogenic VOCs were conducted as a function of the initial VOC/NO x ratio. No significant dependence on the VOC/NO x ratio was observed for the f SOA of 2,3-dihydroxy-4-oxopentanoic acid from toluene and phthalic acid from naphthalene, whereas the f SOA of nitroaromatic compounds such as 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 4-nitrophthalic acid increased with decreasing VOC/NO x ratio. Among seven newly evaluated anthropogenic SOA tracers, we concluded that 3,5-dinitronsalicylic can be used as a toluene SOA tracer, whereas 4-nitrophthalic acid can be used as a naphthalene SOA tracer. Results of kinetic calculations suggest that naphthalene is a major source of 5-nitrosalicylic acid under urban and rural conditions of previous observation studies. The ozonolysis and NO 3 -initiated oxidation of biogenic VOCs were investigated in addition to OH-initiated oxidation of biogenic VOCs. As for biogenic SOA tracers such as pinic acid and 2-methyltetrols, the f SOA value measured for the NO 3 -intiated reaction was lower than that of the OH-initiated oxidation and the f SOA value measured for the ozonolysis was not necessarily close to that of the OH-initiated oxidation. These results suggest that daytime and nighttime biogenic SOA formation events are interpreted by using different sets of the f SOA values. • Ratios of SOA tracer to aerosol mass were measured for aerosol source analysis. • Twenty-eight SOA tracers including new ones formed from four VOCs were measured. • Anthropogenic SOA tracers were studied as a function of initial VOC/NO x ratio. • Biogenic SOA tracers were studied by changing the oxidant of SOA formation.

Syntheses, Structures, and Magnetic Properties of Two Cu(II) Coordination Polymers Based on 4-Nitrophthalic Acid

Syntheses, Structures, and Magnetic Properties of Two Cu(II) Coordination Polymers Based on 4-Nitrophthalic Acid

Evaluating Class B Fire Extinguishing Efficacies of Organic Nitro Compounds Based Aerosol Forming Compositions

Every year, increasing fire accidents worldwide have directed our attention towards an effective fire suppression system. For many decades, Halons have been used as effective fire extinguishing agents. Vienna convention (1985) and Montreal protocol (1987) determined Halons as ozone-depleting agents, and subsequently, their manufacturing is banned by the U.S. Environmental Protection Agency. Thus, against the urgent background of this elimination of Halons, aerosol-based extinguisher resulted as one of the significant Halons substitute technology. The Ozone Depletion Potential and Global Warming Potential values of aerosol extinguishing agents are nearly zero. This has provided thrust for various Universities and research institutions for undertaking numerous projects to develop aerosol-forming pyrotechnic composites for fire fighting applications. In the present work, novel fire extinguishing pyrotechnic compositions were fabricated, in which four different organic nitro compounds, 3,5-dinitrosalicylic acid, 3,5-dinitrobenzoic acid, m-nitrobenzenesulphonate and 3-nitrophthalic acid, were used as the reductant. These nitro compounds undergo rapid redox reaction with strong oxidants to produce aerosol fire extinguishing agents, extinguishing 4.57 KW of small scale n-heptane pool fires in 3 seconds. The fire extinguishing efficacy and thermal characteristics of novel compositions were evaluated against potassium nitrate and phenol formaldehyde resin-based conventional pyrotechnic composition.

Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities

Synthesis of 2-(4-Acetyl-phenyl)-4-nitro-isoindole-1, 3-dione chalcones were performed by fusion of 3-nitro phthalic anhydride with p-aminoacetophenone. Then the later was grinded with different aromatic aldehydes in the presence of sodium hydroxide to produce new chalcones derivatives A3-10 without using any solvent formation of new N-arylphthailimide chalcones were confirmed by FTIR,1HNMR, 13CNMR spectroscopy and all final compounds were tested for their antifungal and antibacterial activity some of them showed more biological activity than the standard drugs..