3-nitrophthalic Acid Research Articles

Synthesis and evaluation of the anxiolytic activity of some phthalimide derivatives in mice model of anxiety.

The aim of the present study was to synthesis a series of phthalimides based on our previous works and examine their anxiolytic properties. Using a three steps process, phthalimides were prepared from the corresponding di-methyl phthalate derivatives. Phthalic anhydride was nitrated to produce 3-nitrophthalic acid. Ring closer of either 3-nitrophthalic acid or di-methyl phthalate with urea were carried out in reflux condition. Final compounds were prepared by base catalyzed condensation of 4-methylbenzoyl chloride, benzoyl chloride and benzyl chloride with the resulting imides. From the tested compounds, only N-benzoyl 3-nitro-phthalimide was shown to produce anxiolytic activity by increasing the number of entries and time spent in open arms at 10 mg/kg.

A 2D homochiral inorganic–organic framework exhibiting a spin–flop transition

A 2D homochiral inorganic-organic framework {[Mn(NPTA)(4,4'-bpy)(H(2)O)]·(H(2)O)(2)}(n) was prepared by assembling achiral polar 4-nitrophthalic acid, manganese ions, and ancillary 4,4'-bipyridine ligands (NPTA = 4-nitrophthalate) (4,4'-bpy = 4,4'-bipyridine). The isomorphous Zn(ii) compound was also prepared as a diamagnetic analogue. Adjacent manganese spin centres are linked by the syn-anti carboxylate to form a helical chain, and chains of the same chirality are connected by 4,4'-bpy ligands to generate a homochiral layered framework. Edge-to-face aromatic interactions between neighboring layers lead to a 3D homochiral supramolecular structure. Magnetization and heat capacity measurements indicate that the framework is a weak antiferromagnet at low applied field. The magnetic interactions between adjacent manganese ions in the helical chain can be fitted using the 1D Fisher model, with 2J/k = -0.68 K and g = 2.00. Moreover, the compound displays a unique field-dependent spin-flop transition in high magnetic fields, with a critical field of 23.6 kOe at 1.9 K.

Synthesis and characterization of new optically active polyamides containing 2-(4-nitro-1,3-dioxoisoindolin-2-yl)succinic acid and aromatic diamines via direct polycondensation

A new class of optically active polyamides (PAs) (6a-e) having 4-nitro-1,3-dioxoisoindolin-2-yl pendent groups were prepared by direct polycondensation reaction of 2-(4-nitro-1,3-dioxoisoindolin-2-yl) succinic acid (4) with various aromatic diamines in a medium consisting of triphenyl phosphite, calcium chloride, pyridine, and N-methyl-2-pyrrolidone. The resulting new polymers were obtained in high yields with inherent viscosities ranging between 0.32 and 0.48 dL/g, and were characterized by elemental analysis, FT-IR spectroscopy, specific rotation, solubility tests, and thermogravimetric analysis techniques (TGA and DTG). Bulky pendent groups of the polymer chains disturb interchain and intrachain interactions and make these PAs readily soluble in polar organic solvents such as N,N-dimethyl acetamide (DMAc), N,N-dimethyl formamide (DMF), dimethyl sulfoxide (DMSO), NMP (N-methyl-2-pyrrolidone), and sulfuric acid. 2-(4-nitro-1,3-dioxoisoindolin-2-yl) succinic acid (4) was prepared by reaction of 3-nitrophthalic anhydride (1) and L-aspartic acid (2) in acetic acid solution.

Synthesis of 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones from Anilines and N-Vinyl Pyrrolidin-2-one Through Imino Diels–Alder Reaction Using 4-Nitro Phthalic Acid as Catalyst

Aryl amines react smoothly and efficiently with N-vinyl pyrrolidin-2-one in the presence of 4-nitro phthalic acid in acetonitrile to afford the corresponding 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-ones in good yields.

Different spatial arrangements in the 4-nitrophthalic acid salts

The crystal structure of three salts of 4-nitrophthalic acid with pyridine ( 1), 2-amino pyridine ( 2) and with 8-aminoquinoline ( 3) are determined. The role of weak and strong hydrogen bonding in crystal packing is ascertained. It is observed that the orientation of the 4-nitrophthalic acid in the lattice is governed by the hydrogen bonding; either sheet-like structure or helical chain can be constructed based on the amine under consideration.

The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids

The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyldiazenyl)aniline], namely isomeric 4-(phenyldiazenyl)anilinium 2-carboxy-6-nitrobenzoate, C(12)H(12)N(3)(+) x C(8)H(4)NO(6)(-), (I), and 4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate, C(12)H(12)N(3)(+) x C(8)H(4)NO(6)(-), (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C(12)H(12)N(3)(+) x C(8)H(4)NO(6)(-) x H(2)O, (III), have been determined at 130 K. In (I) the cation has longitudinal rotational disorder. All three compounds have substructures comprising backbones formed through strong head-to-tail carboxyl-carboxylate hydrogen-bond interactions [graph set C(7) in (I) and (II), and C(8) in (III)]. Two-dimensional sheet structures are formed in all three compounds by the incorporation of the 4-(phenyldiazenyl)anilinium cations into the substructures, including, in the cases of (I) and (II), infinite H-N-H to carboxylate O-C-O group interactions [graph set C(6)], and in the case of (III), bridging through the water molecule of solvation. The peripheral alternating aromatic ring residues of both cations and anions give only weakly pi-interactive step features which lie between the sheets.

Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid

4-Nitrophthalic acid was found to be an effective catalyst for the imino Diels-Alder reaction of N-benzylideneanilines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano- and furanoquinolines in good yields. It was also found that aryl amines react smoothly with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under the same condition to afford the corresponding pyrano- and furanoquinolines in high yields. This catalyst is inexpensive, easily available, water soluble, and stable to aqueous reaction conditions.

Preparation, Thermal Behavior and Non-isothermal Decomposition Reaction Kinetics of Zr(3-NO<sub>2</sub>-PHT)<sub>2</sub>·2H<sub>2</sub>O

用3-硝基邻苯二甲酸、氢氧化钠和硝酸氧锆为原料, 制备了3-硝基邻苯二甲酸锆, 采用元素分析、X射线荧光衍射和FT-IR对其结构进行了表征. 用TG-DTG以及变温固相原位反应池/傅里叶变换红外光谱(RSFT-IR)联用技术研究了3-硝基邻苯二甲酸锆的热分解机理, 对主分解反应的DTG峰进行了数学处理, 计算得到了动力学参数和动力学方程. 结果表明, 3-硝基邻苯二甲酸锆的分解反应总共有4个阶段, 其中主分解反应发生在第2阶段, 主分解反应的表观活化能Ea与指前因子A分别为158.84 kJ·mol-1和10 9.85 s-1, 主分解阶段的反应机理服从一级Mample法则, 主分解反应的动力学方程为dα/dt=10 9.85 (1-α)e -1.91 ×10 4 /T.

Solid–liquid phase equilibrium and phase diagram for ternary 3-nitrophthalic acid–4-nitrophthalic acid–water system at 283.15 K and 333.15 K

In this investigation, the solid–liquid phase equilibrium and the mutual solubility for ternary 3-nitrophthalic acid–4-nitrophthalic acid–water system were determined at 283.15 K and 333.15 K. The phase diagrams of the system were constructed based on the measured solubility. The solid phases formed in the studied system were confirmed by Schreinemakers’ method of wet residues. In addition, the density of equilibrium liquid phase was obtained. At 283.15 K and 333.15 K, both 3-nitrophthalic acid and 4-nitrophthalic acid were formed in the ternary 3-nitrophthalic acid–4-nitrophthalic acid–water system. Adductive compounds existed: 3:1:1 adduct 3-C 6H 3NO 2(COOH) 2·4-C 6H 3NO 2(COOH) 2·H 2O at 283.15 K and 1:1 adduct 3-C 6H 3NO 2(COOH) 2·4-C 6H 3NO 2(COOH) 2 at 333.15 K. The adduct had a bigger crystallization field than 3-nitrophthalic acid or 4-nitrophthalic acid at each studied temperature. The solubility data and the ternary phase diagram for the system 3-nitrophthalic acid–4-nitrophthalic acid–water at 283.15 K and 333.15 K can provide the fundamental basis for preparation of 3-nitrophthalic acid from 3-nitrophthalic acid and 4-nitrophthalic acid mixtures.

Solubility of 3-Nitrophthalic Acid in Different Solvents between 278 K and 353 K

The solubility of 3-nitrophthalic acid in water, methyl acetate, ethyl acetate, butyl acetate, ethyl formate, tetrahydrofuran, acetone, and 1,4-dioxane between 278 K and 353 K were measured using a laser monitoring observation technique. Results of these measurements were correlated with a semi-empirical equation. For the eight solvents studied, the data are well fitted with a semi-empirical equation.

A new family of dimeric lanthanide (III) complexes: Synthesis, structures and photophysical property

A new family of lanthanide complexes with the general formula {[Ln(nphth)(Hnphth)(H 2O) 3·H 2O] 2} n (Ln = Pr, Eu, Gd, Tb, Dy, 1–5 and H 2nphth = 3-nitrophthalic acid) have been synthesized under hydrothermal condition and four of them have been characterized by single-crystal X-ray diffraction and spectroscopy. These compounds are isostructural and the lanthanide ions are all nine coordinated and europium complex emits characteristic red fluorescence of Eu 3+ ions at room temperature while other three lanthanide complexes exhibit the particular emission ascribed H 2nphth ligand, which suggest that the different energy transfer process takes place.

Synthesis, spectral and magnetic susceptibility studies on tetrachloro metal(II)phthalocyanines

The present paper describes a simple method for the synthesis of symmetrically substituted 1,8,15,22-tetrachloro phthalocyanines of copper, cobalt, nickel and zinc. The title complexes are synthesized from the corresponding tetraamino metal phthalocyanines by modified Sandmeyers method and in turn the tetraamino metal phthalocyanines are prepared from 3-nitrophthalic acid. The bluish-green coloured tetrachloro metal phthalocyanine complexes are characterized by elemental, electronic, IR, magnetic susceptibility and X-ray powder diffraction studies to check the purity and the structural integrity. The magnetic susceptibility studies revealed that, the experimental values are higher than that of the spin only value magnetic moment, and the presence of intermolecular co-operative effects.

Retention behavior ofo-phthalic, 3-nitrophthalic, and 4-nitrophthalic acids in ion-suppression reversed-phase high performance liquid chromatography using acids instead of buffers as ion-suppressors

In reversed-phase high performance liquid chromatography, the logarithm of the retention factor, log k, is usually correlated with the logarithm of the octanol-water partition coefficient, log Kow. The k and Kow of an ionizable analyte are greatly influenced by the mobile phase pH. In this paper, log kw of diprotic o-phthalic, 3-nitrophthalic, and 4-nitrophthalic acids, are obtained by extrapolation to pure aqueous fraction of mobile phase in ion-suppression reversed-phase high performance liquid chromatography with acetic acid and perchloric acid as the ion-suppressors. The Kow values of the three analytes are calibrated according to the apparent octanol-water partition coefficient, Kow, under different pH conditions, and the log K"ow values show a much better correlation with log kw than do log Kow. The influences of two ion-suppressors, acetic and perchloric acids, on the retention behavior of these diprotic acids at different pH are contrasted. An abnormal trend is found in the k vs. pHw plot of the acetic acid system when the methanol content is low. A possible reason is that acetic acid is an even stronger organic modifier than methanol, besides being an ion-suppressor. The results make the selection of mobile phase for the separation of acidic compounds by ion-suppression reversed-phase high performance liquid chromatography direct, accurate, and practical.

Brucinium 2-carboxy-6-nitrophthalate dihydrate: the 1:1 proton-transfer compound of brucine with 3-nitrophthalic acid

In the title compound (systematic name: 2,3-dimeth­oxy-10-oxostrychnidinium 2-carb­oxy-6-nitro­phthalate dihydrate), C23H27N2O4+·C8H4NO6−·2H2O, the carboxylic acid and carboxyl­ate groups of the hydrogenphthalate anions form head-to-tail catemeric chains of strong inter­molecular O—H⋯O hydrogen bonds [O⋯O distance = 2.563 (5) Å] along the 21 screw axes parallel to the a axis. The chains further associate with the water mol­ecules, forming sheet structures parallel to (010). The protonated N atom at the 19-position of the brucine mol­ecule forms a peripheral inter­molecular hydrogen bond with the carboxyl­ate group of the anion.

Organically Modified Transition-Metal Oxide Mesoporous Thin Films and Xerogels

Organic molecules have been incorporated into the pore system of mesoporous TiO2 and ZrO2 xerogels and thin films. Surface-modifying functions include alkyl, aryl, amino, sulfonate, thiol, and polyol. Phosphate, phosphonate, carboxylate, and polyphenol were used as grafting groups. The incorporation of these functions into the mesoporous network (typically 2−8 μmol/m2) was monitored by crossing FTIR and EDS. In particular, the cases of dihexadecyl phosphate, monododecyl phosphate, 3-nitrophthalic acid, TIRON (disodium 1,2-dihydroxybenzene, 3,5-disulfonate), and thiol-bearing carboxylates are discussed. Uptake experiments suggest that the pore structure plays a key role in the accessibility of the pore system. Leaching experiments in different solvents and conditions were performed to assess the anchoring of the grafted functions. This permits tailoring of the molecule grafting, from firmly anchored functions to groups with controlled lability.

3-nitrophthalic acid: C(4) and R(2)(2)(8) motifs of O-H...O hydrogen bonds generate sheets which are linked by C-H...O hydrogen bonds.

In molecules of 3-nitrophthalic acid, C(8)H(5)NO(6), the 2-carboxyl group, which is the central of the three substituents, is almost orthogonal to the arene ring, while the other two substituents are effectively coplanar with the ring. The molecules are linked by two O-H...O hydrogen bonds [H...O = 1.86 and 1.89 A, O...O = 2.6983 (13) and 2.6809 (12) A, and O-H...O = 172 and 155 degrees ] into sheets containing alternating R(2)(2)(8) and R(6)(6)(36) rings; these sheets are linked into a three-dimensional framework by a single C-H.O hydrogen bond [H...O = 2.41 A, C.O = 3.2663 (15) A and C-H...O = 150 degrees ].

Fate of isoxaben in a containerized plant rhizosphere system

Commercial production of ornamental plants is an important industry in the United States and involves a complex technology that includes the use of herbicides. Isoxaben { N-[3-(1-ethyl-1-methylpropyl)-5-isoxazolyl]-2,6-dimethoxybenzamide } is a pre-emergence herbicide used for controlling weeds in many areas including containerized ornamental plants. Degradation was studied in potting mix (80% bark, 20% sand) with three different regimes (sterile, bulk and rhizosphere). The rhizosphere regime contained Switch Grass ( Panicum virgatum), and plants were allowed to grow for 14 days before adding isoxaben (10 μg/g potting mix). Isoxaben was degraded to 0.5 μg/g in 60 days giving a half-life of 7 days. Two degradation products were detected: 3-nitrophthalic acid in the rhizosphere and bulk regimes and 4-methoxyphenol in the sterile regime. Microbial population shifts were determined by fatty acid methyl ester profile analysis and were influenced by the introduction of a plant (rhizosphere regime) and by isoxaben addition.

Synthesis of 3-nitrophthalic acid by oxidation of 1-nitronaphthalene using γ-alumina supported ceria(iv) as a catalyst

The synthesis of 3-nitrophthalic acid has been achieved by catalytic oxidation of 1-nitronaphthalene using γ-alumina supported ceria(IV) as a catalyst at 363 K in 80 mol% yield with 98% selectivity.

A convenient synthesis of 5‐ and 8‐nitroquinazoline‐2,4‐dione derivatives

Abstract3‐Nitrophthalic acid 1 was converted selectively to the two regioisomeric monoesters 2 and 3, which were subsequently transformed via Curtius rearrangement to the corresponding 5‐ and 8‐nitroquinazoline‐2,4‐diones 4 and 5, respectively. The reduction of the nitro group produced 5‐ and 8‐aminoquinazoline‐2,4‐diones 6 and 7, respectively, in good yields. The condensation of compounds 7b and 7c with carbon disulfide in pyridine afforded tricyclic derivatives 9, which are analogues of the HIV‐1 reverse transcriptase inhibitor 4,5,6,7‐tetrahydro‐5‐methylimidazo[4,5,1‐jk][1,4]benzodiazepin‐2(1H)‐one(TIBO).

Synthesis of Quinizarin and Its Derivatives under Conditions of Microwave Activation

In a microwave field, phthalic anhydride reacts with p-chlorophenol to give 1,4-dihydroxyanthraquinone (quinizarin) within 10 min. The reaction with 4-chlorophthalic anhydride occurs similarly. Phthalic and chlorophthalic acids can be used instead of anhydrides. 3-Nitrophthalic acid and 3,4,5,6-tetrabromophthalic anhydride do not react with p-chlorophenol under these conditions.