Hydroxynaphthoic Acids Research Articles

Bi-aryl Analogues of Salicylic Acids: Design, Synthesis and SAR Study to Ameliorate Endoplasmic Reticulum Stress.

IntroductionEndoplasmic reticulum (ER) stress condition is characterized as the accumulation of misfolded or unfolded proteins in lumen of ER. This condition has been implicated in various diseases and pathologies including β-cell apoptosis, Alzheimer’s disease and atherosclerosis. We have reported that hydroxynaphthoic acids (HNA), naphthalene analogues of salicylic acid (SA), reduced ER stress. In this study, we explored structural modification to bi-aryl analogues of SA.MethodsPalladium-catalyzed cross-coupling was applied to synthesize bi-aryl analogues of SA. Anti-ER stress activity was monitored by using our cell-based assay system where ER stress is induced by tunicamycin. To monitor ER stress markers, ER stress was induced physiologically relevant palmitate system.ResultsMany analogues decreased ER stress signal induced by tunicamycin. Compounds creating dihedral angle between Ar group and SA moiety generally increased the activity but gave some cytotoxicity to indicate the crucial role of flat conformation of aromatic region. The best compound (16e) showed up to almost 6-fold and 90-fold better activity than 3-HNA and tauro-ursodeoxycholic acid, positive controls, respectively. ER stress markers such as p-PERK and p-JNK were accordingly decreased in Western blotting upon treatment of 16e under palmitate-induced condition.ConclusionAnti-ER stress activity and toxicity profile of bi-aryl analogues of SA could provide a novel platform for potential therapy for protein misfolding diseases.

Blue light-powered hydroxynaphthoic acid-titanium dioxide photocatalysis for the selective aerobic oxidation of amines

Solar photocatalysis is the key to resolve many environmental challenges but is usually hard to achieve over a metal oxide semiconductor. Therefore, assembling π-conjugated molecules onto semiconductors becomes an efficient approach to solar conversion via ligand-to-metal charge transfer. Here, a rational design of ligands for titanium dioxide (TiO2) is presented to produce robust visible light photocatalysts. Three hydroxynaphthoic acids (HNAs) were selected as ligands by extending an extra benzene ring of salicylic acid (SA) at 3,4 or 4,5 or 5,6 positions. These ligands could regulate the performance of TiO2 in which 2-hydroxy-1-naphthoic acid (2H1NA) endows the best outcome. In detail, blue light-powered cooperative photocatalysis of 2H1NA-TiO2 with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO, 5 mol%) inaugurates the expeditious formation of imines by oxidation of amines with atmospheric oxygen (O2). Interestingly, the increase of the O2 pressure from 1 atm to 0.4 MPa promoted the selective oxidation of benzylamine but thereafter declined with a further boost to 0.6 MPa. Notably, an electron transfer between the oxidatively quenched 2H1NA-TiO2 and TEMPO is established, offering a new pathway for environmental applications. This work presents a strategy in designing cutting-edge visible light photocatalysts via altering semiconductors with surface ligands.

Prototropic forms of hydroxy derivatives of naphthoic acid within deep eutectic solvents.

Deep eutectic solvents (DESs) are not only recognized as benign and inexpensive alternatives to ionic liquids, they offer a unique solvation milieu due to the varying H-bonding capabilities of their constituents. Proton-transfer involving a probe and its prototropic forms strongly depend on the H-bonding nature of the solubilizing media. The presence of prototropic forms of three probes, 1-hydroxy-2-naphthoic acid (1,2-HNA), 3-hydroxy-2-naphthoic acid (3,2-HNA), and 6-hydroxy-2-naphthoic acid (6,2-HNA) is investigated in two DESs, named ChCl:urea and ChCl:glycerol, constituted of H-bond acceptor choline chloride and different H-bond donors, urea and glycerol, respectively, in a 1 : 2 mole ratio under ambient conditions. While 1,2-HNA and 3,2-HNA exhibit an intramolecular H-bonding ability, 6,2-HNA does not. In contrast to common polar solvents, where the monoanionic emitting form of 1,2-HNA is also supported along with the neutral one, in both the DESs only the neutral emitting form exists. Addition of acid to the two DESs, respectively, fail to generate the monocationic form of the probe. Addition of a base to ChCl:urea results in the generation of the monoanionic form; even a very high strength of the base fails to generate the monoanionic emitting form in ChCl:glycerol. Relatively higher H-bond donating acidity of ChCl:glycerol results in added hydroxyl getting involved in H-bonding with alcohol functionalities of ChCl:glycerol leading to the absence of proton extraction to create the monoanionic form of the probe. Only the monoanionic emitting form of 3,2-HNA is present in ChCl:urea; in ChCl:glycerol, due to its higher H-bond donor acidity, the neutral emitting form is also detected. Addition of high strength of acid to ChCl:urea does result in formation of the neutral emitting form. Addition of an aqueous base results in the formation of the dianionic form of 3,2-HNA in ChCl:urea; however, in ChCl:glycerol, the added base fails to convert the neutral form of this probe to the monoanionic form as efficiently as that in ChCl:urea. The monoanionic (carboxylate) form of 6,2-HNA exits in ChCl:urea, whereas the neutral form is present in ChCl:glycerol due to its higher H-bond donating acidity. Addition of an acid can induce a shift in prototropic equilibrium towards the neutral form of 6,2-HNA in ChCl:urea; no change is observed in the behavior of this probe in ChCl:glycerol as the acid is added. Both the DESs support the dianionic form of 6,2-HNA in the presence of the base; the added base helps extract both -OH and -COOH protons of this probe. The H-bond donor component of the DES is clearly established to play a critical role in the prototropic behavior of the probe.

Modulation of Solid-State Optical Properties of o-Hydroxynaphthoic Acids through Formation of Charge Transfer Cocrystals with TCNB

Charge transfer cocrystals offer an opportunity to alter the photophysical characteristics of organic chromophores in the solid state. A set of new charge transfer cocrystals of three positional is...

Functional Characterization of a Novel Member of the Amidohydrolase 2 Protein Family, 2-Hydroxy-1-Naphthoic Acid Nonoxidative Decarboxylase from Burkholderia sp. Strain BC1.

The gene encoding a nonoxidative decarboxylase capable of catalyzing the transformation of 2-hydroxy-1-naphthoic acid (2H1NA) to 2-naphthol was identified, recombinantly expressed, and purified to homogeneity. The putative gene sequence of the decarboxylase (hndA) encodes a 316-amino-acid protein (HndA) with a predicted molecular mass of 34 kDa. HndA exhibited high identity with uncharacterized amidohydrolase 2 proteins of various Burkholderia species, whereas it showed a modest 27% identity with γ-resorcylate decarboxylase, a well-characterized nonoxidative decarboxylase belonging to the amidohydrolase superfamily. Biochemically characterized HndA demonstrated strict substrate specificity toward 2H1NA, whereas inhibition studies with HndA indicated the presence of zinc as the transition metal center, as confirmed by atomic absorption spectroscopy. A three-dimensional structural model of HndA, followed by docking analysis, identified the conserved metal-coordinating and substrate-binding residues, while their importance in catalysis was validated by site-directed mutagenesis. Microbial nonoxidative decarboxylases play a crucial role in the metabolism of a large array of carboxy aromatic chemicals released into the environment from a variety of natural and anthropogenic sources. Among these, hydroxynaphthoic acids are usually encountered as pathway intermediates in the bacterial degradation of polycyclic aromatic hydrocarbons. The present study reveals biochemical and molecular characterization of a 2-hydroxy-1-naphthoic acid nonoxidative decarboxylase involved in an alternative metabolic pathway which can be classified as a member of the small repertoire of nonoxidative decarboxylases belonging to the amidohydrolase 2 family of proteins. The strict substrate specificity and sequence uniqueness make it a novel member of the metallo-dependent hydrolase superfamily.

Anti-diabetic effect of 3-hydroxy-2-naphthoic acid, an endoplasmic reticulum stress-reducing chemical chaperone

Lots of experimental and clinical evidences indicate that chronic exposure to saturated fatty acids and high level of glucose is implicated in insulin resistance, beta cell failure and ultimately type 2 diabetes. In this study, we set up cell-based experimental conditions to induce endoplasmic reticulum (ER) stress and insulin resistance using high concentration of palmitate (PA). Hydroxynaphthoic acids (HNAs) were formerly identified as novel chemical chaperones to resolve ER stress induced by tunicamycin. In this study, we found the compounds have the same suppressive effect on PA-induced ER stress in HepG2 cells. The representing compound, 3-HNA reduced PA-induced phosphorylation of JNK, IKKβ and IRS1 (S307) and restored insulin signaling cascade which involves insulin receptor β, IRS1 and Akt. The insulin sensitizing effect of 3-HNA was confirmed in 3T3-L1 adipocytes, where the compound augmented insulin signaling and glucose transporter 4 (GLUT4) membrane translocation. 3-HNA also protected the pancreatic beta cells from PA-induced apoptosis by reducing ER stress. Upon 3-HNA treatment to ob/ob mice at 150mg/kg/day dosage, the diabetic parameters including glucose tolerance and systemic insulin sensitivity were significantly improved. Postmortem examination showed that 3-HNA markedly reduced ER stress and insulin resistance in the liver tissues and it sensitized insulin signaling in the liver and the skeletal muscle. Our results demonstrated that 3-HNA can sensitize insulin signaling by coping with lipotoxicity-induced ER stress as a chemical chaperone and suggested it holds therapeutic potential for insulin resistance and type 2 diabetes.

Carboxylation of hydroxyarens with metal alkyl carbonates

AbstractThe objective of this work was to investigate the possibility of using alkali metal salts of ethylcarbonic acid as a carboxylating reagent in phenol (naphthols) carboxylation and developing a new and simple method for the synthesis of hydroxybenzoic and hydroxynaphthoic acids having broad practical application. It was found that sodium ethyl carbonate and potassium ethyl carbonate can be successfully used as carboxylating agents in carboxylation of phenol and naphthols. For the first time, the effects of the gaseous medium (air, carbon dioxide, argon), pressure, temperature and reaction time on the proceedings of the carboxylation reactions were examined. Simple and convenient procedures for the syntheses of o- and p-hydroxybenzoic, p-aminosalicylic, 1-hydroxy-2-naphthoic, 1-hydroxy-4-naphthoic and 2-hydroxy-3-naphthoic acids were developed. New efficient technologies for preparation of drugs salicylic acid (antiseptic activity), p-aminosalicylic acid (antituberculous activity) and p-hydroxybenzoic acid (bactericide activity) based on carboxylation reactions of phenol and m-aminophenol with sodium and potassium salts of ethyl carbonic acid were worked out.

Benz[ a ]anthracene Biotransformation and Production of Ring Fission Products by Sphingobium sp. Strain KK22

A soil bacterium, designated strain KK22, was isolated from a phenanthrene enrichment culture of a bacterial consortium that grew on diesel fuel, and it was found to biotransform the persistent environmental pollutant and high-molecular-weight polycyclic aromatic hydrocarbon (PAH) benz[a]anthracene. Nearly complete sequencing of the 16S rRNA gene of strain KK22 and phylogenetic analysis revealed that this organism is a new member of the genus Sphingobium. An 8-day time course study that consisted of whole-culture extractions followed by high-performance liquid chromatography (HPLC) analyses with fluorescence detection showed that 80 to 90% biodegradation of 2.5 mg liter(-1) benz[a]anthracene had occurred. Biodegradation assays where benz[a]anthracene was supplied in crystalline form (100 mg liter(-1)) confirmed biodegradation and showed that strain KK22 cells precultured on glucose were equally capable of benz[a]anthracene biotransformation when precultured on glucose plus phenanthrene. Analyses of organic extracts from benz[a]anthracene biodegradation by liquid chromatography negative electrospray ionization tandem mass spectrometry [LC/ESI(-)-MS/MS] revealed 10 products, including two o-hydroxypolyaromatic acids and two hydroxy-naphthoic acids. 1-Hydroxy-2- and 2-hydroxy-3-naphthoic acids were unambiguously identified, and this indicated that oxidation of the benz[a]anthracene molecule occurred via both the linear kata and angular kata ends of the molecule. Other two- and single-aromatic-ring metabolites were also documented, including 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid and salicylic acid, and the proposed pathways for benz[a]anthracene biotransformation by a bacterium were extended.

Hydroxynaphthoic Acids Identified in a High Throughput Screening Potently Ameliorate Endoplasmic Reticulum Stress as Novel Chemical Chaperones

Folding of newly synthesized protein occurs in endoplasmic reticulum (ER) and is assisted by chaperone molecules. In ER stress conditions, misfolded proteins are enriched in a lumen of ER perturbing its normal function, which triggers cellular self-defense mechanism, the unfolded protein response (UPR). It was reported that tunicamycin-induced ER stress can be modulated with high concentration of chemicals such as 4-phenylbutyric acid and salicylate. In search of assay systems to identify such compounds, we have developed a cell-based reporter assay where renilla luciferase activity is driven by glucose-regulated protein 78 (GRP78) promoter. Using our reporter assay, we have screened chemical libraries and found that hydroxynaphthoic acids, especially 1-, 3-, and 6-hydroxy-2-naphthoic acids, potently decrease the ER stress signal, showing an order of magnitude better activity than salicylate. UPR markers such as GRP78, C/EBP homology protein (CHOP) and phosphorylated protein kinase RNA-activated (PKR)-like ER kinase (PERK) were significantly down-regulated with hydroxynaphthoic acids in western blot. Among the analogues, 1-hydroxy-2-naphthoic acid was the most potent in down-regulating those UPR markers. Further, both phosphorylated inositol-requiring enzyme 1α (IRE1α) and spliced form of X-box binding protein 1 (XBP1) were decreased in the protein and the mRNA level, implying both PERK and IRE1α branches in UPR mechanism are controlled with hydroxynaphthoic acids. Taken together, it was suggested that hydroxynaphthoic acids exert their ER stress-reducing activity prior to the UPR activation as chemical chaperones do. In summary, we report a cell-based assay system for the screening of ER stress-reducing compounds and hydroxynaphthoic acids as novel series of chemical chaperones.

Mycobacterium aromativorans JS19b1T degrades phenanthrene through C-1,2, C-3,4 and C-9,10 dioxygenation pathways

Mycobacterium aromativorans strain JS19b1T can utilize phenanthrene as a sole source of carbon and energy. Strain JS19b1T degrades phenanthrene through highly branched metabolic pathways, including dioxygenation on C-1,2, C-3,4 and C-9,10 positions and ring opening by both ortho- and meta-cleavage. The presence of novel metabolic pathways was confirmed by replacement cultivation using synthetic metabolite standards. The metabolites were isolated and identified by gas chromatography-mass spectrometry. Both ortho and meta-cleavage products of 1,2- and 3,4-dihydroxyphenanthrene were detected. Two ortho-cleavage products, 1-[(E)-2-carboxyvinyl]-2-naphthoic acid and 2-[(E)-2-carboxyvinyl]-1-napthoic acid were further metabolized to naphthalene-1,2-dicarboxylic acid and then to 1,2-dihydroxynaphthalene, which can also be produced from the meta-cleavage products hydroxynaphthoic acids. These results suggest that part of the branched pathways is merged into 1,2-dihydroxynaphthalene. The concentrations of the products from C-9,10 dioxygenation were higher than those from other pathways. C-9,10 dioxygenation of phenanthrene produced phthalic acid through decarboxylation and mono-/di-oxygenation. The diverse phenanthrene metabolic pathways in JS19b1T give a new insight of the bacterial degradation of polycyclic aromatic hydrocarbons.

Meta-Cleavage of hydroxynaphthoic acids in the degradation of phenanthrene by Sphingobium sp. strain PNB

Polycyclic aromatic hydrocarbons (PAHs) comprise a group of priority organic pollutants that are toxic and/or carcinogenic. Phenanthrene, the simplest PAH among recognized priority pollutants, is commonly used as a model compound for the study of PAH biodegradation. Sphingobium sp. strain PNB, capable of degrading phenanthrene as a sole carbon and energy source, was isolated from a municipal waste-contaminated soil sample. A combination of chromatographic and spectrometric analyses, together with oxygen uptake and enzyme activity studies, suggested the presence of phenanthrene degradation pathways in this strain. Identification of metabolites suggested that initial dioxygenation of phenanthrene took place at both 3,4- and 1,2-carbon positions; meta-cleavage of resultant diols led to the formation of 1-hydroxy-2-naphthoic acid and 2-hydroxy-1-naphthoic acid, respectively. The hydroxynaphthoic acids, in turn, were metabolized by a meta-cleavage pathway(s), leading to the formation of 2,2-dicarboxychromene and 2-hydroxychromene-2-glyoxylic acid, respectively. These metabolites were subsequently transformed to catechol via salicylic acid, which further proceeds towards the tricarboxylic acid cycle leading to complete mineralization of the compound phenanthrene. The present study establishes the metabolism of hydroxynaphthoic acids by a meta-cleavage pathway in the degradation of phenanthrene, expanding our current understanding of microbial degradation of PAHs.

Inclusion compounds of hydroxynaphthoic acids: co-crystal vs. salt formation

6-Hydroxy-2-naphthoic acid, H1, forms solvates with 1,4-dioxane (DIOX) and dimethyl sulfoxide (DMSO), and their structures are stabilized by host–host and host–guest hydrogen bonds. H1 forms a hydrated salt with 1,4-diazabicyclo[2.2.2]octane, DABCO, with stoichiometry 2H1·2DABCO·3H2O. Two other naphthoic acid isomers, 1-hydroxy-2-naphthoic acid, H2, and 3-hydroxy-2-naphthoic acid, H3, form salts with DABCO with host : guest ratios of 2 : 1. The kinetics of thermal decomposition of the H1·½DIOX compound yields an activation energy of ∼60 kJ mol−1 for the desolvation reaction.

Biocatalytic Synthesis of Dihydroxynaphthoic Acids by Cytochrome P450 CYP199A2

CYP199A2, a bacterial P450 monooxygenase from Rhodopseudomonas palustris, was found to exhibit oxidation activity towards three hydroxynaphthoic acids. Whole cells of the recombinant Escherichia coli strain expressing CYP199A2 efficiently catalyzed the regioselective oxidation of 1-, 3-, and 6-hydroxy-2-naphthoic acids to produce 1,7-, 3,7-, and 6,7-dihydroxynaphthoic acid respectively. These results suggest that CYP199A2 might be a useful oxidation biocatalyst for the synthesis of dihydroxynaphthoic acids.

Discovery of 2‐Naphthoic Acid Monooxygenases by Genome Mining and their Use as Biocatalysts

The large pool of cytochrome P450 (P450) open-reading frames identified in genome sequences has attracted much attention as a resource for new oxidation biocatalysts. P450 genes were cloned from genome-sequenced bacteria and coexpressed with putidaredoxin and its reductase genes to provide the redox partners of P450 in Escherichia coli. Whole-cell assays were performed with 2-naphthoic acid as a substrate. Hydroxylated naphthoic acid products were rapidly detected with two reagents showing different colors in the presence of the products. Two P450s, CYP199A1 and CYP199A2, were found to hydroxylate the substrate to 7- and 8-hydroxy-2-naphthoic acids. The CYP199A1 whole-cell biocatalyst converted 1 mM 2-naphthoic acid to 0.27 mM 7-hydroxy-2-naphthoic acid and 0.53 mM 8-hydroxy-2-naphthoic acid. CYP199A2 exhibited similar regioselectivity to CYP199A1. Furthermore, we found that 8-hydroxy-2-naphthoic acid emits near-white fluorescence when exposed to UV light. These P450s will provide a facile and environmentally friendly synthetic approach to the hydroxynaphthoic acids.

Biodegradation of phenanthrene by Pseudomonas sp. strain PPD: purification and characterization of 1-hydroxy-2-naphthoic acid dioxygenase

Pseudomonas sp. strain PPD can metabolize phenanthrene as the sole source of carbon and energy via the 'phthalic acid' route. The key enzyme, 1-hydroxy-2-naphthoic acid dioxygenase (1-HNDO, EC 1.13.11.38), was purified to homogeneity using a 3-hydroxy-2-naphthoic acid (3-H2NA)-affinity matrix. The enzyme was a homotetramer with a native molecular mass of 160 kDa and subunit molecular mass of approximately 39 kDa. It required Fe(II) as the cofactor and was specific for 1-hydroxy-2-naphthoic acid (1-H2NA), with K(m) 13.5 microM and V(max) 114 micromol min(-1) mg(-1). 1-HNDO failed to show activity with gentisic acid, salicylic acid and other hydroxynaphthoic acids tested. Interestingly, the enzyme showed substrate inhibition with a K(i) of 116 microM. 1-HNDO was found to be competitively inhibited by 3-H2NA with a K(i) of 24 microM. Based on the pH-dependent spectral changes, the enzyme reaction product was identified as 2-carboxybenzalpyruvic acid. Under anaerobic conditions, the enzyme failed to convert 1-H2NA to 2-carboxybenzalpyruvic acid. Stoichiometric studies showed the incorporation of 1 mol O(2) into the substrate to yield 1 mol product. These results suggest that 1-HNDO from Pseudomonas sp. strain PPD is an extradiol-type ring-cleaving dioxygenase.

Conversion of polycyclic aromatic hydrocarbons by Sphingomonas sp. VKM B-2434

A versatile bacterial strain able to convert polycyclic aromatic hydrocarbons (PAHs) was isolated, and a conversion by the isolate of both individual substances and PAH mixtures was investigated. The strain belonged to the Sphingomonas genus as determined on the basis of 16S rRNA analysis and was designated as VKM B-2434. The strain used naphthalene, acenaphthene, phenanthrene, anthracene and fluoranthene as a sole source of carbon and energy, and cometabolically oxidized fluorene, pyrene, benz[a]anthracene, chrysene and benzo[a]pyrene. Acenaphthene and fluoranthene were degraded by the strain via naphthalene-1,8-dicarboxylic acid and 3-hydroxyphthalic acid. Conversion of most other PAHs was confined to the cleavage of only one aromatic ring. The major oxidation products of naphthalene, phenanthrene, anthracene, chrysene, and benzo[a]pyrene were identified as salicylic acid, 1-hydroxy-2-naphthoic acid, 3-hydroxy-2-naphthoic acid, o-hydroxyphenanthroic acid and o-hydroxypyrenoic acid, respectively. Fluorene and pyrene were oxidized mainly to hydroxyfluorenone and dihydroxydihydropyrene, respectively. Oxidation of phenanthrene and anthracene to the corresponding hydroxynaphthoic acids occurred quantitatively. The strain converted phenanthrene, anthracene, fluoranthene and carbazole of coal-tar-pitch extract.

Photo-Induced Relaxation and Proton Transfer in Some Hydroxy Naphthoic Acids in Polymers

Photophysical and photochemical properties of 3-hydroxy-2-naphthoic acid [3,2-HNA] and 1-hydroxy-2naphthoic acid [1,2-HNA] in different aprotic, protic, and ion exchange (Nafion) polymers have been described in this article. In both molecules, intramolecular hydrogen bond (IMHB) exists between OH and COOH functional groups. Both 3,2-HNA and 1,2-HNA form different emitting species in different polymeric media. Fluorescence characteristic of 3,2-HNA is found to depend on its concentration, nature of the microenvironment, and wavelength of excitation, while 1,2-HNA is less susceptible to these changes. 3,2-HNA exhibits dual fluorescence band (normal and large Stokes shifted) in aprotic and only a single large Stokes shifted fluorescence in protic polymers, while 1,2-HNA shows a single fluorescence band along with weak phosphorescence emission in these polymers. Both excited-state inter and intramolecular proton transfer (ESPT) take place in 3,2-HNA in aprotic and protic polymers, resulting in large Stokes shifted emission band. A competition between ESIPT and excimer formation is observed by the appearance of rise time on increasing the concentration of 3,2-HNA in protic polymer. In Nafion film, 3,2-HNA is present as a cationic as well as neutral species. The presence of extra protons in Nafion film facilitates excited-state intramolecular proton transfer (ESIPT) in the neutral species of 3,2-HNA and gives large Stokes shifted emission (10 500 cm(-1)). No such effect is observed in 1,2-HNA doped in Nafion film. It is observed that, depending on the position of the IMHB ring, the electronic spectra get modified and the strength of IMHB is affected by the micro-environment of the polymer which alters the photophysics of these molecules.

Magnetic properties of two double-layer structures built from hydroxynaphthoic acids and manganese

Double-layer structures consisting of alternating polar and non-polar layers have been prepared using Mn2+ ions and o-hydroxynaphthoic acids. The polar layers contain the Mn2+ ions, carboxylate groups, hydroxy groups and water molecules. The non-polar layers are built up from the naphthalene moieties. In catena-poly[[diaquamanganese(II)]bis(mu-3-hydroxy-2-naphthoato-kappa2O:O')] (also called manganese 3-hydroxy-2-naphthoate dihydrate), [Mn(C11H7O3)2(H2O)2]n, (I), the Mn2+ ions are connected by carboxylate groups to form two-dimensional networks. This compound shows distinct antiferromagnetic interactions and long-range ordering at low temperature. In contrast, tetraaquabis(1-hydroxy-2-naphthoato-kappaO)manganese(II), [Mn(C11H7O3)2(H2O)4], (II), which lacks a close linkage between the Mn2+ ions, reveals purely paramagnetic behaviour. In (II), the Mn2+ ion lies on an inversion centre.

The Influence of Hydrophobic Counterion on the Phase Behavior of Ionic Surfactants

Abstract This paper investigates the effects of counterion microenvironments on the phase properties of ionic surfactants. The results of different isomers of hydroxy naphthoic acids (x, y HNC) and the cationic surfactant hexadecyltrimethylammonium hydroxide (HTAOH) are included. Mixing 3,2 HNC, 2,1 HNC or 6,2 HNC with micellar solutions of HTAOH transforms the micellar microstructure into different morphologies depending on the counterion microenvironments. The vesicles at equal concentration ratio of 3,2 HNC/HTAOH and 2,1 HNC/HTAOH have been characterized by freeze fracture electron microscopy (FF-TEM) and small angle neutron scattering (SANS). 6,2 HNC/HTAOH system does not form a liquid crystalline phase (Lα-phase) at and above the equal concentration ratio. With these systems the effects that the hydrophobic counterion microenvironments have on the aggregate microstructure, rheological behavior, Krafft temperature and other physiochemical properties are discussed.

Formation Constants of Chromium(III), Scandium(III) and Yttrium(III) Complexes of Some Hydroxy Naphthoic Acids

The complexes of chromium(III), scandium(III) and yttrium(III) formed by 1-hydroxy-2-naphthoic acid (1,2-HNA: H2L) and 3-hydroxy-2-naphthoic acid (3,2-HNA: H2L) were investigated by potentiometry and spectroscopy at 25+/-0.1 degrees C and at an ionic strength of 0.1 M KNO3 in 50% ethanol-water (v/v) medium. The stoichiometries of these three M(III) complexes formed with these hydroxy-naphthoic acids and with hydroxo ion were defined and their formation constants were determined and compared. Thus, the removing capacities of these ligands could be examined by calculating the equilibrium concentration of Cr(III) that exists in the discharge water of various industries since Cr(III) ions are the main pollutants present during waste water treatment in our city, Bursa.