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Oxyacid

An oxyacid, also known as an oxoacid, is a that contains oxygen, at least one other , and atoms bound to oxygen, from which it can lose hydrons to form a conjugate ; this distinguishes it from hydracids like HCl, which lack oxygen in the acidic group. These acids typically follow the general formula \ce{H_mXO_n}, where \ce{X} is a central atom—usually a or early —and m and n indicate the number of hydrogen and oxygen atoms, respectively, with the acidic hydrogens attached to oxygen atoms. Common examples of oxyacids include (\ce{H2SO4}), (\ce{HNO3}), (\ce{H3PO4}), and (\ce{HClO4}), many of which are derived from the of nonmetallic oxides with and play crucial roles in , biological systems, and laboratory chemistry. Oxyacids are often polyprotic, meaning they can donate multiple protons, with successive dissociation constants decreasing due to the increasing stability of the conjugate bases. Naming of oxyacids follows systematic conventions based on the central atom and the number of oxygen atoms relative to the highest ; for instance, acids with fewer oxygen atoms end in -ous (e.g., \ce{H2SO3} as ), while those with more end in -ic (e.g., \ce{H2SO4} as ), with prefixes like hypo- for the lowest and per- for the highest oxygen content. Their acidity trends are influenced by the of the central atom—higher electronegativity increases acidity (e.g., \ce{HOCl} > \ce{HOBr} > \ce{HOI})—and the number of oxygen atoms to it, as additional oxygens stabilize the conjugate through inductive effects (e.g., \ce{HClO4} > \ce{HClO3} > \ce{HClO2} > \ce{HClO}).

Definition and Nomenclature

Definition

Oxyacids, also known as oxoacids or oxygen acids, are acids containing oxygen in the acidic group, specifically compounds with at least one bound to oxygen, which is further connected to a central atom—typically a , , or early . These acids produce their conjugate base, an oxoanion, upon dissociation by losing one or more hydron ions (H⁺). The general structural formula for oxyacids is often expressed as H_m XO_n, where X represents the central atom, and m and n are positive integers denoting the number of and oxygen atoms, respectively. In these structures, the acidic hydrogens are directly attached to oxygen atoms, enabling ionization in aqueous solutions. The term "oxyacid" is primarily used for inorganic acids and differs from binary acids (hydracids), such as (HCl), which consist solely of and a single element without oxygen in the acidic group. Although the structural definition could apply to some acids like carboxylic acids (which have oxygen in the acidic ), such compounds are conventionally classified as acids rather than oxyacids. The term "oxyacid" originated in the early (first recorded 1830–1840), during a period of advancing chemical understanding that included the formulation of acid-base theory by in the 1880s. Common examples include (H₂SO₄) and (HNO₃).

Nomenclature

The nomenclature of oxyacids follows the recommendations of the International Union of Pure and Applied Chemistry (IUPAC), which provide both systematic and retained traditional names to reflect the of the central atom and the number of oxygen atoms present. In the traditional system, preferred for common use, the name is derived from the root of the central atom, with suffixes indicating the : the "-ous" suffix denotes a lower (fewer oxygen atoms), while the "-ic" suffix denotes a higher (more oxygen atoms). Prefixes modify these when multiple s exist: "hypo-" indicates the lowest state, and "per-" the highest. Systematic names, less commonly used, employ additive based on coordination entities, such as "tetraoxidosulfate(2−) with 2H" for . Common naming patterns illustrate these rules across element families. For sulfur oxyacids, the lower oxidation state compound H_2SO_3 is named (+4 oxidation state), while the higher state H_2SO_4 is (+6 oxidation state). Similarly, chlorine oxyacids progress with increasing oxygen and oxidation state: HClO as (+1), HClO_2 as (+3), HClO_3 as (+5), and HClO_4 as (+7). These patterns ensure names convey the relative oxygen content and reactivity trends associated with oxidation states. The corresponding oxyanions are named by replacing the acid suffixes with "-ate" or "-ite": for example, the anion from , SO_4^{2-}, is , while from , SO_3^{2-}, it is . Prefixes carry over similarly, yielding (ClO^-) from and (ClO_4^-) from . This anion nomenclature extends to salts and other derivatives, maintaining consistency with the parent acid. Certain oxyacids retain traditional or trivial names despite available systematic alternatives, as approved by IUPAC for historical and practical reasons. For instance, HNO_3 is universally called , a retained name, rather than the additive form "trioxonitrate(1−) with H." Other retained examples include (H_3PO_4) and (H_2CO_3), which prioritize familiarity in scientific and contexts. These exceptions are listed in IUPAC tables to guide consistent usage.

Properties

Physical Properties

Oxyacids exhibit a range of physical states at room temperature, primarily as liquids or solids, depending on their molecular structure and intermolecular forces. Common examples include nitric acid (HNO₃), which appears as a fuming, pale yellow to reddish-brown liquid with a suffocating odor, and sulfuric acid (H₂SO₄), a colorless, viscous, oily liquid. Pure phosphoric acid (H₃PO₄) is a transparent crystalline solid, though it is typically handled as a concentrated aqueous solution that remains liquid at room temperature. Perchloric acid (HClO₄) is also a clear, colorless liquid in its concentrated form. Most oxyacids are highly soluble in water, owing to extensive hydrogen bonding between their hydroxyl groups and water molecules, often resulting in miscibility. For instance, sulfuric acid is completely miscible with water, releasing significant heat upon dilution, while nitric acid is similarly fully miscible. Many oxyacids form azeotropic mixtures with water, which complicates their purification by distillation; sulfuric acid forms a maximum-boiling azeotrope at approximately 98.3 wt% H₂SO₄, and nitric acid at 68 wt% HNO₃. The melting and s of oxyacids show trends influenced by molecular weight, the number of bonds, and overall , with higher values generally observed for those capable of stronger intermolecular interactions. has a relatively low point of 83 °C and of -42 °C, whereas boils at 337 °C with a of 10 °C, reflecting its greater and -bonding capacity. melts at 42 °C, and at -18 °C, with the latter at 203 °C. These properties establish the scale of thermal stability for handling and processing oxyacids. Densities and viscosities among oxyacids vary significantly, often higher than those of simple binary acids due to their polar nature and molecular size. , for example, has a of 1.84 g/cm³ at 20 °C and a of 21 ·s at 25 °C, contributing to its syrupy texture. In contrast, has a lower of 1.51 g/cm³ at 20 °C and of 0.75 ·s at 25 °C, making it more fluid. The following table summarizes key physical properties for representative oxyacids:
OxyacidState at 25 °CMelting Point (°C)Boiling Point (°C)Density (g/cm³ at 20–25 °C)Viscosity (mPa·s at 25 °C)
HNO₃831.510.75
H₂SO₄103371.8421
H₃PO₄ (85% aq.)~21~1581.68~40
HClO₄ (70%)-182031.67~3.5

Chemical Properties

Oxyacids are characterized by their ability to donate protons from hydroxyl groups attached to a central atom, leading to ionization in according to the general equilibrium: \ce{H_m XO_n ⇌ H+ + H_{m-1} XO_n^-} The acidity strength is measured by the pKa value, defined as \mathrm{p}K_a = -\log K_a, where K_a is the acid dissociation constant. Strong oxyacids, such as perchloric acid (\ce{HClO4}), have very low pKa values (approximately -10), indicating nearly complete dissociation, while weak oxyacids like carbonic acid (\ce{H2CO3}) have higher pKa values, with the first dissociation constant at 6.35. Several factors govern the acidity of oxyacids. The electronegativity of the central atom plays a key role: higher electronegativity enhances the polarity of the O-H bond, weakening it and promoting proton release; for instance, acids with the same structure but more electronegative central atoms are stronger. Bond strength also influences acidity, as shorter, stronger bonds to oxygen stabilize the conjugate base less effectively. Furthermore, the oxidation state of the central atom affects strength—higher oxidation states increase acidity by drawing electron density away from the O-H bond through inductive effects, as seen in series like \ce{H2SO3} (weaker) versus \ce{H2SO4} (stronger). In addition to acidity, many oxyacids exhibit oxidation-reduction properties due to the variable oxidation states of their central atoms. These compounds often function as oxidizing agents, particularly when the central atom is in a high oxidation state, allowing reduction to lower states. For example, nitric acid (\ce{HNO3}), with nitrogen at +5 oxidation state, oxidizes metals such as copper to form nitrates and nitrogen oxides. Sulfuric acid (\ce{H2SO4}), featuring sulfur at +6, acts as an oxidant in its concentrated form, dehydrating or oxidizing organic materials and metals. Certain oxyacids also display hydrolysis tendencies and can form polymeric structures via reactions, where is eliminated to link units. (\ce{H3PO4}), for instance, undergoes polymerization to yield linear chains of phosphate units, resulting in polyphosphoric acids used in various applications. Some oxyacids or their derived anions further exhibit amphoteric behavior, capable of acting as either acids or bases; hydrogen carbonate ion (\ce{HCO3^-}), from , exemplifies this by donating or accepting protons depending on solution .

Classification and Examples

Inorganic Oxyacids

Inorganic oxyacids encompass a diverse group of compounds where a central atom from non-carbon elements, such as , chalcogens, or pnictogens, is bonded to hydroxyl groups and oxygen, exhibiting acidic behavior upon . These acids play crucial roles in , , and , with their properties varying based on the central atom's and .

Halogen Oxyacids

The oxyacids, primarily derived from , illustrate a trend in and acidity that increases with the oxidation state of the . (HClO), with chlorine in the +1 oxidation state, is a weak acid (pKa ≈ 7.5) and highly unstable, readily decomposing to release ions used as disinfectants. (HClO₂, +3 state) is stronger (pKa ≈ 2.0) but still prone to , while (HClO₃, +5 state) exhibits greater and oxidizing power, often employed in explosives and bleaching agents. (HClO₄, +7 state) is the strongest and most stable, with a pKa < -10, serving as a powerful oxidant and in due to its non-coordinating anion. This progression in arises from enhanced delocalization of electrons in higher-oxidation-state species, reducing reactivity toward decomposition.

Sulfur Oxyacids

Sulfur oxyacids form a key family, with (H₂SO₄) being the most prominent due to its industrial significance. (H₂SO₃), existing mainly in aqueous solutions from SO₂ dissolution, is unstable and decomposes readily into and , acting as a weak diprotic acid (pKa₁ ≈ 1.9, pKa₂ ≈ 7.2) with reducing properties. In contrast, H₂SO₄ is a strong diprotic acid (pKa₁ < 0, pKa₂ ≈ 1.9), highly stable, and exhibits dehydrating action on carbohydrates and concentrated oxidizing behavior, essential for producing fertilizers, batteries, and dyes. (H₂S₂O₃), analogous to sulfuric acid but with one atom replaced by , is unstable and decomposes to and H₂SO₃, yet its salts (thiosulfates) are stable reducing agents used in and as antidotes for .

Nitrogen Oxyacids

Nitrogen oxyacids are vital in and explosives, with (HNO₂) and (HNO₃) as primary examples. HNO₂, a weak acid (pKa ≈ 3.3), is unstable in acidic conditions and decomposes to and , serving as a mild oxidant in organic reactions. HNO₃, conversely, is a strong monoprotic acid (pKa ≈ -1.4) and potent oxidant capable of dissolving metals and nitrates, widely used in fertilizer production (e.g., ) and as a nitrating agent in explosives like ; its stability stems from the high of (+5).

Phosphorus Oxyacids

Phosphorus oxyacids are polyprotic and feature P-H bonds in lower-oxidation forms, influencing their reducing capabilities. (H₃PO₂), with phosphorus in the +1 state, is a monoprotic (pKa ≈ 1.2) and strong reductant due to its P-H bond, used in electroless plating and as an . (H₃PO₃, +3 state) is diprotic (pKa₁ ≈ 2.1, pKa₂ ≈ 7.2), with one ionizable P-OH group, exhibiting reducing properties and applications in inhibition. (H₃PO₄, +5 state) is a triprotic (pKa₁ ≈ 2.1, pKa₂ ≈ 7.2, pKa₃ ≈ 12.7), stable and non-reducing, forming solutions and essential in fertilizers, detergents, and food additives like soft drinks.

Other Families

Carbonic acid (H₂CO₃), formed by CO₂ hydration, is a weak diprotic acid (pKa₁ ≈ 6.4, pKa₂ ≈ 10.3) central to biological regulation and in beverages, though it decomposes readily in solution. (H₄SiO₄) is a very weak acid (pKa ≈ 9.8) that polymerizes to form silica gels and contributes to diatom shells in aquatic environments. (H₃BO₃), a monoprotic weak acid (pKa ≈ 9.2), acts as a Lewis acid through boron-oxygen interactions, used in antiseptics, , and nuclear reactors as a absorber.

Organic Oxyacids

Organic oxyacids are a class of acids featuring a central or carbon-based framework bonded to oxygen-containing functional groups that confer acidity, distinguishing them from inorganic oxyacids by their incorporation of substituents. These compounds play key roles in , , and biological processes due to their tunable properties and reactivity. The primary examples of organic oxyacids are carboxylic acids, which possess the general R-COOH, where R represents a or an group such as an alkyl or aryl chain. In this structure, the carboxyl group (-COOH) consists of a carbonyl (C=O) bonded to a hydroxyl (-OH) group, enabling proton donation from the acidic . A representative example is acetic acid (CH_3COOH), with a pK_a value of 4.76, indicating moderate acidity suitable for applications in buffers and esterifications. Sulfonic acids represent another important family, characterized by the formula R-SO_3H, where the sulfonyl group (-SO_3H) imparts significantly greater acidity than carboxylic acids due to the electron-withdrawing effect of the sulfur-oxygen bonds. Methanesulfonic acid (CH_3SO_3H) exemplifies this class, with a pK_a of approximately -1.9, making it a strong acid comparable to mineral acids and useful in catalysis and as a non-oxidizing alternative to sulfuric acid. Other notable organic oxyacids include phosphonic acids, with the general structure R-PO(OH)_2, where a phosphorus atom is bonded to one R group, a double-bonded oxygen, and two hydroxyl groups, facilitating applications in and flame retardants. An example is aminomethylphosphonic acid, which demonstrates the versatility of this motif in coordination chemistry. Sulfinic acids, denoted as R-SO_2H, feature a sulfur atom in the +4 bonded to R, an oxygen, and a hydroxyl group; they are isoelectronic with carboxylic acids but less stable, often serving as intermediates in sulfur oxidation pathways. In contrast to many inorganic oxyacids, which can exhibit very strong acidity (e.g., pK_a < 0), organic oxyacids are generally weaker, with acidity modulated by substituents on the R group—electron-withdrawing groups enhance while electron-donating ones reduce it. This tunability is biologically significant, as groups in contribute to the zwitterionic nature of proteins, influencing folding, , and pH-dependent interactions in .

Preparation and Stability

Synthetic Methods

Oxyacids are commonly synthesized through oxidation reactions that increase the of the central atom in lower oxyanions. For instance, (H₂SO₄) is produced industrially via the , where (SO₂), derived from the combustion of or ores, is oxidized to (SO₃) using a vanadium pentoxide (V₂O₅) catalyst at elevated temperatures (400–500°C) and pressures. The SO₃ is then hydrated to form H₂SO₄: \text{SO}_3 + \text{H}_2\text{O} \rightarrow \text{H}_2\text{SO}_4 This method yields high-purity acid on a large scale, with global production of approximately 261 million tonnes as of 2024. Hydrolysis of acid halides or anhydrides provides a laboratory-scale route to several oxyacids by replacing halogen or anhydride linkages with hydroxyl groups. Phosphoric acid (H₃PO₄), an inorganic oxyacid, is prepared by the controlled hydrolysis of phosphorus pentachloride (PCl₅) with excess water: \text{PCl}_5 + 4\text{H}_2\text{O} \rightarrow \text{H}_3\text{PO}_4 + 5\text{HCl} This exothermic reaction requires careful temperature control to avoid side products like phosphorous acid. Similarly, the hydration of SO₃, an anhydride, directly yields H₂SO₄, as noted above, and is integral to the final absorption step in the contact process. Electrochemical oxidation enables the synthesis of highly oxidized oxyacids from precursors. (HClO₄), the strongest of the chlorine oxyacids, is produced by anodic oxidation of (HCl) or solutions in electrolytic cells, stepwise forming , , and ions before acidification: \text{Cl}^- \rightarrow \text{ClO}^- \rightarrow \text{ClO}_3^- \rightarrow \text{ClO}_4^- or anodes are typically used, with current efficiencies up to 90% at 50–70°C, though the process is energy-intensive and suited for high-purity needs. On an industrial scale, nitric acid (HNO₃), a key inorganic oxyacid, is synthesized via the Ostwald process, which couples the Haber-Bosch ammonia synthesis with catalytic oxidation. Ammonia (NH₃) is oxidized over a platinum-rhodium gauze catalyst at 800–900°C to nitric oxide (NO), followed by air oxidation to nitrogen dioxide (NO₂) and absorption in water: $4\text{NH}_3 + 5\text{O}_2 \rightarrow 4\text{NO} + 6\text{H}_2\text{O}, \quad 2\text{NO} + \text{O}_2 \rightarrow 2\text{NO}_2, \quad 3\text{NO}_2 + \text{H}_2\text{O} \rightarrow 2\text{HNO}_3 + \text{NO} This process accounts for the majority of global HNO₃ production, approximately 58 million tonnes as of 2024, primarily for fertilizers.

Stability and Decomposition

The thermal stability of oxyacids tends to increase with the of the central atom, as more electronegative atoms form stronger bonds with oxygen, reducing the tendency for bond cleavage. For of oxyacids sharing the same central atom, stability also rises with the of that atom, owing to higher bond orders that resist decomposition. For instance, among the oxyacids of , (HClO, Cl in +1 ) is highly unstable and decomposes readily via the reaction $2 \text{HClO} \rightarrow 2 \text{HCl} + \text{O}_2, often catalyzed by or metallic impurities. In contrast, (HClO₄, Cl in +7 ) exhibits greater thermal stability than lower oxidation state analogs; aqueous solutions up to 70% concentration are stable at , though heating concentrated solutions requires caution due to potential decomposition. Decomposition reactions of oxyacids typically involve the release of , s, or lower-oxidation-state species, driven by thermodynamic favorability. (H₂SO₃) decomposes upon heating to yield and : \text{H}_2\text{SO}_3 \rightarrow \text{H}_2\text{O} + \text{SO}_2. Similarly, (HNO₂) undergoes : $3 \text{HNO}_2 \rightarrow \text{HNO}_3 + 2 \text{NO} + \text{H}_2\text{O}, producing and . These processes highlight how lower-oxidation-state oxyacids are more prone to of oxygen or ligands. Several factors influence oxyacid , including , temperature, and the presence of catalysts. Elevated temperatures accelerate rates following Arrhenius , while acidic conditions can either stabilize or hasten breakdown depending on the specific acid— for example, HNO₂ is faster at low due to effects. Catalysts such as transition metals or light further promote instability by lowering activation energies for bond breaking. offers a means to enhance stability; in the case of phosphoric acids, formation of polyphosphoric acids through increases thermal resistance, enabling applications at higher temperatures without rapid degradation. Safety considerations are paramount for certain oxyacids, particularly peroxoacids like peroxomonosulfuric acid (H₂SO₅), which exhibit explosive decomposition under , , or , releasing oxygen and generating rapid buildup. These compounds demand strict handling protocols, including below critical temperatures and avoidance of initiators, to mitigate risks of .

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    Piranha Solutions - - Division of Research Safety | Illinois
    Like most peroxides, peroxymonosulfuric acid can be highly unstable and/or explosive depending on conditions [2]. Because piranha solutions are highly corrosive ...Missing: peroxoacids | Show results with:peroxoacids