Sulfonic Salt Research Articles

Legacy and emerging per- and polyfluoroalkyl substances suppress the neutrophil respiratory burst

Per- and polyfluoroalkyl substances (PFASs) are used in a multitude of processes and products, including nonstick coatings, food wrappers, and fire-fighting foams. These chemicals are environmentally-persistent, ubiquitous, and can be detected in the serum of 98% of Americans. Despite evidence that PFASs alter adaptive immunity, few studies have investigated their effects on innate immunity. The report here presents results of studies that investigated the impact of nine environmentally-relevant PFASs [e.g. perfluorooctanoic acid (PFOA), perfluorooctane sulfonic acid potassium salt (PFOS-K), perfluorononanoic acid (PFNA), perfluorohexanoic acid (PFHxA), perfluorohexane sulfonic acid (PFHxS), perfluorobutane sulfonic acid (PFBS), ammonium perfluoro(2-methyl-3-oxahexanoate) (GenX), 7H-perfluoro-4-methyl-3,6-dioxa-octane sulfonic acid (Nafion byproduct 2), and perfluoromethoxyacetic acid sodium salt (PFMOAA-Na)] on one component of the innate immune response, the neutrophil respiratory burst. The respiratory burst is a key innate immune process by which microbicidal reactive oxygen species (ROS) are rapidly induced by neutrophils in response to pathogens; defects in the respiratory burst can increase susceptibility to infection. The study here utilized larval zebrafish, a human neutrophil-like cell line, and primary human neutrophils to ascertain whether PFAS exposure inhibits ROS production in the respiratory burst. It was observed that exposure to PFHxA and GenX suppresses the respiratory burst in zebrafish larvae and a human neutrophil-like cell line. GenX also suppressed the respiratory burst in primary human neutrophils. This report is the first to demonstrate that these PFASs suppress neutrophil function and support the utility of employing zebrafish larvae and a human cell line as screening tools to identify chemicals that may suppress human immune function.

Facile synthesis of sulfonyl fluorides from sulfonic acids.

Herein, we demonstrate two complementary strategies for the syntheses of sulfonyl fluorides using sulfonic acids and their salts. One strategy involves the conversion of sulfonic acid sodium salts to sulfonyl fluorides using thionyl fluoride in 90-99% yields in one hour. Lessons learned from the mechanism of this reaction also have enabled a complementary deoxyfluorination of sulfonic acids using Xtalfluor-E® - a bench stable solid - allowing for the conversion of both aryl and alkyl sulfonic acids and salts to sulfonyl fluorides in 41-94% yields. Notably, using Xtalfluor-E® enabled milder conditions and the use of both sulfonic acids and their sodium salts.

Ion migration inhibition and defect passivation via sulfonate salt coordination for high-performance perovskite solar cells with enhanced phase stability

In this work, sulfonate salt additive 6-bromo-2-naphthyl triflate (BNT) is introduced into perovskites to inhibit ion migration and improve phase stability, achieving a champion efficiency of 21.95% and improving long-term stability.

(Digital Presentation) Physicochemical Characterization of Sulfonate-Based Phosphonium Ionic Liquids

Ionic liquids (ILs) have unique physicochemical properties such as favorable solubility of organic and inorganic compounds, relatively high ionic conductivity, no measurable vapor pressure, high thermal stability, low flammability, etc. ILs are also promising liquid materials available for various applications because their function can be easily controlled by changing the combination of cations and anions and by introducing substituents. Although many kinds of ILs have already been investigated, phosphonium cation based ILs have rarely been proposed. We have previously designed and synthesized the phosphonium ILs together with typical sulfonylamide-based anions such as bis(trifluoromethylsulfonyl)amide and bis(fluorosulfonyl)amide anions.1,2) On the other hand, interests in phosphonium ILs consisting of the other anions is increasing for diverse applications. In this work, we design and prepare the ILs based on tetrabutylphosphonium cation (P4444 +) together with various sulfonate-based anions (Fig. 1), characterizing their physicochemical properties as a new family of ILs. The phosphonium IL was prepared by an aqueous neutralization reaction of tetrabutylphosphonium hydroxide with the stoichiometric amounts of various sulfonic acids. The obtained phosphonium ILs were isolated by water evaporation, and were dried in vacuo for at least 1 day. The physicochemical properties of ILs, e.g. density, viscosity, conductivity (ac impedance method) and thermal decomposition temperature (thermogravimetric analysis), were measured under argon atmosphere.The phosphonium salts based on unsubstituted sulfonate anions such as SO3CH3, SO3CH2CH3 and SO3(CH2)2CH3 were white crystalline solids at room temperature, whereas both amino- and hydroxy- substituted sulfonate salts were viscous liquids at room temperature. All phosphonium salts obtained were hydrophilic. Table 1 summarizes the physicochemical properties of phosphonium ILs based on amino- and hydroxy-substituted sulfonate anions. These phosphonium ILs exhibited considerably high viscosities when compared to the previously published viscosity value of P4444-lactate IL (415 mPa s at 25 °C)3), which suggests that the electrostatic interaction between P4444 cation and the sulfonate anions is much stronger than those in the case of carboxylate-based phosphonium ILs. It should be noted that P4444-SO3(CH2)3NH2 obviously indicated not only the highest density but also the highest viscosity and the lowest conductivity, which might be due to the fact that the IL has the largest anion to give a significant van der Waals interaction. Figure 1

Ionic Push-Pull Polythiophenes: A Further Step towards Eco-Friendly BHJ Organic Solar Cells.

Four new conjugated polymers alternating benzothiadiazole units and thiophene moieties functionalized with ionic phosphonium or sulfonic acid salts in the side chains were synthesized by a postfunctionalization approach of polymeric precursors. The introduction of ionic groups makes the conjugated polymers soluble in water and/or polar solvents, allowing for the fabrication of bulk heterojunction (BHJ) solar cells using environmentally friendly conditions. All polymers were fully characterized by spectroscopic, thermal, electrochemical, X-ray diffraction, scanning electron, and atomic force techniques. BHJ solar cells were obtained from halogen-free solvents (i.e., ethanol and/or anisole) by blending the synthesized ionic push–pull polymers with a serinol-fullerene derivative or an ionic homopolymer acting as electron-acceptor (EA) or electron-donor (ED) counterparts, respectively. The device with the highest optical density and the smoothest surface of the active layer was the best-performing, showing a 4.76% photoconversion efficiency.

Effect of synthesized sulfonate derivatives as nucleating agents on crystallization behavior of poly(lactic acid)

ABSTRACT The improvement of the crystallization of poly(lactic acid) (PLA) is one of the key areas to allow PLA to perform better at higher temperature and load bearing. Due to its slow crystallization rate, either organic or inorganic nucleating agents (NAs) can be used to improve the crystallization rate of PLA. In the case of organic NAs, aromatic sulfonate salt and bisamide compounds are promising ones because they can control better clarity. The aim of this work was to study the crystallization behavior of PLA using as-synthesized dimethyl 5-sulfoisophthalate sodium salt (SSIPA) as a nucleating agent in comparison with the commercial sulfonate salt (LAK-301). Two grades of PLA (PLA L105 and PLA 3251D) were used in this study. PLA samples were prepared by internal mixer and compression molding. All samples were investigated by DSC and POM. The results from DSC showed that after introducing the nucleating agents into PLA, the crystallinity in all samples was improved. The highest crystallinity at 57.48% was obtained from PLA L105/SSIPA1.0. Isothermal crystallization kinetics showed the improvement in overall crystallization rate of PLA with nucleating agents. The lowest half time crystallization obtained was 1.19 min for PLA L105/SSIPA1.0 at 135 °C. The results from POM indicated the substantial increase of the nucleus density and smaller spherulite size upon adding nucleating agents.

Combining enabling formulation strategies to generate supersaturated solutions of delamanid: In situ salt formation during amorphous solid dispersion fabrication for more robust release profiles

Poor solubility is a major challenge that can limit the oral bioavailability of many drugs, including delamanid, a weakly basic nitro-dihydro-imidazooxazole derivative used to treat tuberculosis. Amorphous solid dispersion (ASD) can improve the bioavailability of poorly water-soluble compounds, yet drug crystallization is a potential failure mechanism, particularly as the drug loading increases. The goal of the current study was two-fold: to enhance the stability of amorphous delamanid against crystallization and to improve drug release by developing ASDs containing the salt form of the drug. Various sulfonate salts of delamanid were prepared in amorphous form and evaluated for their tendency to crystallize and undergo chemical degradation following storage at 40 °C/75% relative humidity. Drug release was evaluated by a two-stage dissolution test consisting of an initial low pH stage, followed by transfer to a higher pH medium. For ASDs of the free base, small amounts of crystallinity during preparation were found to limit the drug release. Delamanid salts with sulfonic acids showed considerably improved amorphous stability. Tosylate, besylate, edisylate, and mesylate salts had high glass transition temperatures as well as good chemical and physical stability. In addition, a remarkable improvement in the drug release was observed when ASDs were prepared with these salts in comparison to the free base form. Specifically, ASDs with hydroxypropyl methylcellulose phthalate (HPMCP) at 25% drug loading exhibited near-complete drug release for all four sulfonate salts. These findings suggest that the dual strategy combining salt formation with ASD formation is a promising approach to alter the crystallization tendency and to improve drug release of problematic poorly water-soluble compounds.

Arenediazonium sulfonates: synthesis, comparison of structural and physicochemical properties

Aromatic diazonium salts are important building blocks in organic synthesis. The present review is concerned with such aromatic diazonium sulfonates as tosylates, dodecylbenzenesulfonates, triflates, camphorsulfonates, silica sulfates. The first part of the review provides information on the synthesis and application of these diazonium salts. It is shown that these diazonium compounds are easily synthesized by diazotization of anilines with sodium nitrite or alkyl nitrites in the presence of corresponding sulfonic acids with high yields. These diazonium salts have found wide application in the synthesis of aromatic azides, halides, triazenes, azo dyes, stilbenes, biaryls, etc. The second part of the article presents information on the comparison of the results of X-ray analysis, infrared spectroscopy and thermal analysis. The structure of diazonium sulfonate salts corresponds to the structure of classical diazonium salts (chlorides, sulfates, tetrafluoroborates). A significant difference between arenediazonium sulfonates and other diazonium salts is their explosion safety and stability in an individual form. Arenediazonium tosylates, triflates and camphorasulfonates are easily soluble both in water and in polar organic solvents. Arenediazonium dodecylbenzenesulfonates are soluble in nonpolar organic media. These features of sulfonate salts are paramount for distinguishing characteristics of the effect of the acid anion on the stability, solubility and reactivity of diazonium salts.

Visible Light-Driven Synthesis of Amine–Sulfonate Salt Derivatives: A Step towards Green Approach

In this work, a novel strategy for the straightforward visible-light-driven synthesis of biologically active, industrially important, and stable amine–sulfonate salts have been reported from p-Toluenesulfonic acid and amines, which provide extremely high yield without side product formation. The reaction was performed without catalyst under visible light irradiation and had an excellent functional group tolerance. The structure of the prepared compounds were confirmed through 1H NMR, 13C NMR, and Mass spectroscopic studies, and similarly, the molecular structure of compound 3b was established through single-crystal XRD-analysis. The advantages of this method meet the requirements of sustainable and green synthetic chemistry, and it provides a direct way to create valuable amine-sulfonate salt.

Study on Adsorption Characteristics of Sulfonate Gemini Surfactant on Lignite Surface

In order to explore the adsorption characteristics of sulfonate gemini surfactants on the surface of lignite, the molecular dynamics simulation method was used, and A kind of sulfonic acid bis sodium salt (S2) and the sodium dodecyl sulfate (SDS) were selected. A binary model of surfactant/lignite adsorption system and a ternary model of water/surfactant/lignite system were constructed, and a series of properties such as adsorption configuration, interaction energy, order parameters, relative concentration distribution, number of hydrogen bonds, etc., were analyzed. The results showed that the adsorption strength of S2 on the surface of lignite was higher than that of SDS. The results indicated that the large-angle molecular chain in S2 tended to become smaller, the small-angle molecular chain tended to become larger, and the angle between the molecular chains and the Z axis tended to be concentrated, making the formed network structure denser during the adsorption process. The number of hydrogen bonds in the water-coal system was 42, and the number of hydrogen bonds in the system after S2 adsorption was 15, which was much lower than the 23 hydrogen bonds in the system after SDS adsorption, and S2 could better adsorb and wrap the oxygen-containing groups on the surface of the lignite. The comparative study of the adsorption characteristics of the two surfactants on the surface of lignite can help us better understand the influence of the surfactant structure on the adsorption strength. The research results have important theoretical and practical significance for developing new surfactants, and enriching and developing the basic theory of coal wettability.

Tuning the Cloud-Point and Flocculation Temperature of Poly(2-(diethylamino)ethyl methacrylate)-Based Nanoparticles via a Postpolymerization Betainization Approach.

The ability to tune the behavior of temperature-responsive polymers and self-assembled nanostructures has attracted significant interest in recent years, particularly in regard to their use in biotechnological applications. Herein, well-defined poly(2-(diethylamino)ethyl methacrylate) (PDEAEMA)-based core–shell particles were prepared by RAFT-mediated emulsion polymerization, which displayed a lower-critical solution temperature (LCST) phase transition in aqueous media. The tertiary amine groups of PDEAEMA units were then utilized as functional handles to modify the core-forming block chemistry via a postpolymerization betainization approach for tuning both the cloud-point temperature (TCP) and flocculation temperature (TCFT) of these particles. In particular, four different sulfonate salts were explored aiming to investigate the effect of the carbon chain length and the presence of hydroxyl functionalities alongside the carbon spacer on the particle’s thermoresponsiveness. In all cases, it was possible to regulate both TCP and TCFT of these nanoparticles upon varying the degree of betainization. Although TCP was found to be dependent on the type of betainization reagent utilized, it only significantly increased for particles betainized using sodium 3-chloro-2-hydroxy-1-propanesulfonate, while varying the aliphatic chain length of the sulfobetaine only provided limited temperature variation. In comparison, the onset of flocculation for betainized particles varied over a much broader temperature range when varying the degree of betainization with no real correlation identified between TCFT and the sulfobetaine structure. Moreover, experimental results were shown to partially correlate to computational oligomer hydrophobicity calculations. Overall, the innovative postpolymerization betainization approach utilizing various sulfonate salts reported herein provides a straightforward methodology for modifying the thermoresponsive behavior of soft polymeric particles with potential applications in drug delivery, sensing, and oil/lubricant viscosity modification.

Highly Soluble Imidazolium Ferrocene Bis(sulfonate) Salts for Redox Flow Battery Applications.

Redox flow batteries (RFBs) are scalable devices that employ solution-based redox active components for scalable energy storage. To maximize energy density, new highly soluble catholytes and anolytes need to be synthesized and evaluated for their electrochemical performance. To that end, we synthesized a series of imidazolium ferrocene bis(sulfonate) salts as highly soluble catholytes for RFB applications. Six salts with differing alkyl chain lengths on the imidazolium cation were synthesized, characterized, and electrochemically analyzed. While aqueous solubility was significantly improved, the reactivity of the imidazolium cation and the increased viscosities of the salt solutions in water (which increase with increasing imidazolium chain length) limit the applicability of these materials to RFB design.

Spray drift deposition comparison of fluorimetry and analytical confirmation techniques.

Tracer dyes are often used as surrogates to characterize pesticide spray drift and it is assumed that they accurately reflect analytical measurement of active ingredients; however, the validity of this assumption remains inconclusive. Consequently, the influence of measurement technique on the magnitude of deposition of spray drift was investigated using spray drift samples evaluated by traditional analytical techniques (HPLC-MS/MS) and fluorimetry (1,3,6,8-pyrene-tetra sulfonic acid tetrasodium salt dye tracer). The experiment was conducted in a low-speed wind tunnel under controlled meteorological conditions. The herbicide mesotrione was sprayed through three spray air induction nozzles (anvil deflector flat fan TTI11004; flat fan AI11004; flat fan AIXR11003). Spray drift deposition samples were collected using stainless steel discs pairs placed side by side in the center of the wind tunnel at distances of 5, 10, 20, 30, and 40 ft (1.5, 3.1, 6.1, 9.1, and 12.2m) from the spray nozzle. The analytical technique determined pesticide concentration on one disc per pair, and the other was evaluated by fluorimetry. The experimental results, analyzed using the linear split-split plot model, revealed that median deposition concentrations were 15% higher using the tracer dye fluorescence method relative to the analytical method, potentially due in part to procedural recovery inefficiencies of the analytical method (the mean overall procedural recovery result and RSD was 87% ± 6.4% (n=12). This relationship was consistent and held true for the three nozzle types at all distances within the wind tunnel. © 2021 Society of Chemical Industry.

Study of the Electrochemical Behavior of Merocyanine and Merocarbocyanine Salts and Their Transformation into Π-Electron Donor Molecules, Namely Tetrathiatetraazafulvalenes

An electrochemical study using the cyclic voltammetry method was carried out on some previously prepared merocyanines salts, namely thiazolideniumsulfonate salts 5a-b, and thiazolidenium chloride salts 6a-b, and merocarbocyanines salts, namely alkylidenthiazolidenium sulfonate salt 5c, and alkylidenthiazolidenium chloride salt 6c. These salts are transformed by dimerization in situ in a voltammetric cell into tetrathiatetraazafulvalenes (TTTAFs) 7a-b, 7’a-b, 8c, and 8'c supposed to be π-electron donor molecules due to the existing conjugation in their structure. The structure of all new chemically synthesized molecules was confirmed by IR, 1H-NMR, 13C-NMR, and MS. The transformation of salts into TTTAF was confirmed by a reversible voltammogram curve and the variation of observed potentials.

Supramolecular Synthon Approach in Designing Organic Sulfonates as Supramolecular Gelators: An Easily Accessible Topical Gel with Antibacterial Properties

The supramolecular synthon approach in the context of the crystal engineering rationale has been exploited to synthesize a new series of primary ammonium sulfonate salts derived from primary alkyl amines with varying alkyl chain lengths (An = CH3–(CH2)n–NH2; n = 2–11, 13–15, 17) and naphthalene-2-sulfonic acid (N2S) as potential supramolecular gelators. The sulfonate salts AnN2S with n ≥ 9 showed the ability to immobilize a number of polar and nonpolar solvents including dimethyl sulfoxide/water, resulting in supramolecular gels which were characterized by dynamic rheology and transmission electron microscopy. Single-crystal X-ray diffraction studies carried out on eight such salts confirmed the presence of gel-inducing hydrogen bonded supramolecular synthons. Anti-bacterial studies (zone inhibition, turbidity, and tetrazolium assays) revealed that the salt A14N2S had the ability to kill the Gram-positive bacterium Staphylococcus aureus. Laser scanning confocal microscopy and flow cytometry data taken under various staining conditions suggested reactive oxygen species-mediated RNA depletion as the plausible cause of bacterial cell death in the presence of the gelator salt. Shear thinning of the aqueous gel of A14N2S along with its anti-bacterial activity indicated that it could be a potential candidate for topical application.

A combination of modeling and experimental approaches to investigate the novel nicotinohydrazone Schiff base and its complexes with Zn(II) and ZrO(II) as inhibitors for mild-steel corrosion in molar HCl

Two novel metal-complexes of 5-sodium sulfonate-2-hydroxybenzylidene)nicotinohydrazone (H2LCs) with Zn2+ and ZrO2+ ions were synthesized and characterized (ZnLCs and ZrOLCs), respectively. Condensation of nicotinohydrazide with salicylaldehyde-5-sodium sulfonate salt afforded H2LCs. Inhibition effectiveness of H2LCs and its complexes with Zn(II) and Zr(II) for M-steel in a 1.0 M HCl solution was examined by electrochemical (EOCP vs. time, impedance spectroscopy (EIS) and potentiodynamic polarization (PDP)) methods. In comparison with H2LCs, ZnLCs and ZrOLCs display enhanced protection capacities. Particularly, the ZrOLCs compound displays higher protection power, and the efficacy is up to 97.4% at 5 × 10−4 mol L − 1 at 303 K. PDP studies exhibited that the as-prepared additives act as inhibitors of the mixed-kind, and adsorbed on M-steel surface via chemisorption following the Langmuir isotherm model. The surface morphology inspections (FE-SEM/EDX, and FT-IR) display that the M-steel interface was inhibited by titled compounds. To get a preferable comprehension of the adsorption of compound species on the steel interface, a detailed modeling investigation was accomplished using Monte Carlo (MC) simulation and DFT calculations. QSAR model also investigated via multiple linear regression method. The current report delivers very significant outcomes in designing and fabricating sustainable inhibitors with high protection capacity.

I+/TBHP Catalysis For Tandem Oxidative Cyclization To Indolo[2,3‐b]quinolines

AbstractWe report a chemoselective tandem oxidative cyclization/aromatization of indole derivatives tethered to aniline sulfonamides using catalytic amount of tetrabutylammonium iodide in the presence of tert‐butyl hydroperoxide (TBHP) as an oxidant under nearly neutral conditions at room temperature. The corresponding indolo[2,3‐b]quinolines were obtained as sulfonate salts, which could be easily isolated in analytically pure form via only a simple filtration of the crude reaction mixture. The natural product quinindoline could be easily obtained after basic work‐up of the sulfonate salt. Control experiments revealed that both ionic and radical active species could be generated in situ under mild conditions for the corresponding oxidative transformations to proceed in a chemoselective manner.

Impedance spectroscopy of polyaniline coated hydrogel

A sulfonic acid functional hydrogel was prepared starting from the copolymerization of 2-acrylamido-2-methyl-1-propanesulfonic acid as monomer and tetraallyl ammonium bromide as a cross-linking agent in the presence of K2S2O8 as a radical initiator. Aniline was interacted with the hydrogel, and oxidative polymerization reaction of anilinium sulfonate salt containing hydrogel was performed by using ammonium persulfate to obtain conducting gel material. The electrical/dielectric properties of the PANI-coated hydrogel were analyzed using impedance spectroscopy. The frequency dependence of the real (e′) and imaginary (e″) parts of the dielectric constant (e), dissipation factor, the real (σ′) and imaginary (σ″) parts of the ionic conductivity (σ), Cole–Cole plots and impedance parameters values for the PANI-coated hydrogel were analyzed in the frequency range of 100 Hz–15 MHz at room temperature. PANI-coated hydrogel shows the non-Debye relaxation type in the materials. The conductivity mechanisms of PANI-coated hydrogel are super linear power law and extended pair approximation.

Water-soluble Cu(II)-complexes of Schiff base amino acid derivatives as biological reagents and sufficient catalysts for oxidation reactions

Two novel water-soluble Cu(II) complexes (Cu-PSA and Cu-PSL) are synthesized from easily accessible Schiff base amino acid ligands (HPSA and HPS), as sodium sulfonate salts, obtained from D,L-phenylalanine and D,L-leucine, respectively. Their chemical composition is confirmed using various spectroscopic analyses (NMR, UV–vis, IR and mass spectroscopies, CHN micro-analyses, conductivities, TGA, and magnetism). The effect of sodium sulfonate group (Na+ SO3− group) on the chemical behavior of both Cu-PSA and Cu-PSL complexes is studied catalytically and biologically. Catalytically, Cu-PSA and Cu-PSL exhibit high reactivity in the (ep)oxidation of 1,2-cyclooctene and benzyl alcohol in polar reaction media, (acetonitrile or water) at 80 °C, under homogeneous reaction condition. Biologically, the Cu-complexes and their ligands (HPSA and HPS) are tested for antimicrobial activity against some pathogens strains. Both Cu-complexes reveal higher performance than their corresponding ligands. Cu-PSA and Cu-PSL complexes are also examined for ctDNA-interaction, which studied using various techniques including spectroscopy, viscosity and gel-electrophoresis. Despite, their low lipophilicity due to the sodium sulfonate group (salting group), they show potentially high electrostatic interaction with ctDNA. The binding potential of these compounds is also investigated by molecular docking showing the role of the central metal ion (Cu2+) and the salting group in the ctDNA interaction. For anticancer reactivity, both ligands (HPSA, HPSL), and their complexes (Cu-PSA or Cu-PSL) are examined against hepatocellular carcinoma (HepG2) cell line, breast carcinoma (MCF7) cell line and colon carcinoma (HCT-116) cell line. The obtained results are encouraging and after optimization the Cu-complexes could be potentially anticancer drug candidates.

Toxicity of dinonylnaphthalene sulfonates to Pimephales promelas and epibenthic invertebrates

Dinonylnaphthalene sulfonic acids (NSAs) are high production volume chemicals that are used primarily as additives in a wide range of industrial products (i.e., coatings, sealants, fuels, metal-extractants, paints, rubber materials). This study examined the effect of three NSA congeners on freshwater organisms: barium dinonylnaphthalene sulfonate (BaDNS), calcium dinonylnaphthalene sulfonate (CaDNS), and dinonylnaphthalene disulfonic acid (DNDS). Chronic effects were characterized by exposing fertilized fathead minnow eggs to sediment-associated NSAs and measuring various developmental and growth endpoints for 21 d. No effects in hatch success and larval growth were observed when fathead minnow eggs were exposed to CaDNS and DNDS concentrations up to 246 and 798 μg/g dry weight, respectively, in spiked sediment (~2% organic carbon). However, when NSAs were associated with substrate containing no organic carbon (sand), EC50s for fathead minnow hatch success, larval growth, biomass production, and overall survival were 58.3, 18.8, 15.5, and 13.8 μg/L, respectively, for CaDNS. Acute effect characterization was also conducted in water-only exposures for the three NSA congeners using the freshwater amphipod Hyalella azteca, the pulmonate snail Planorbella pilsbryi, and larval freshwater mussels Lampsilis cardium and Lampsilis siliquoidea. The sulfonate salts (BaDNS and CaDNS) were significantly more acutely toxic to all tested invertebrates in the water-only exposures, with LC50s ranging from 0.47 to 12.1 μg/L, compared to DNDS (LC50s ≥ 98.2 μg/L). This is the first study to provide empirical data on the aquatic toxicity of three NSA congeners.