Fact-checked by Grok 2 weeks ago

Carboxylate

A carboxylate is the anionic conjugate base formed by the deprotonation of a carboxylic acid, characterized by the general formula RCOO⁻, where R represents an alkyl or aryl group, and featuring a resonance-stabilized structure between a carbonyl (C=O) and an alkoxide (C-O⁻) moiety.^[1]^[2] This resonance delocalization of the negative charge over the two oxygen atoms enhances the stability of the carboxylate ion compared to the neutral carboxylic acid, contributing to the relatively strong acidity of carboxylic acids (pKa values typically 4-5).^[1]^[3] Carboxylates play a central role in organic and biochemical processes due to their ability to form salts with metal cations, enabling solubility in water and facilitating coordination in metalloproteins and enzymes.^[4]^[5] In aqueous environments, carboxylate ions exhibit amphiphilic properties, with the charged head group promoting hydration and the hydrophobic R tail influencing self-assembly in surfactants and biological membranes.^[6] Their reactivity includes acting as nucleophiles in alkylation reactions and serving as key intermediates in metabolic pathways such as the citric acid cycle, where acetate and other carboxylates are central to energy production; upon protonation, the resulting carboxylic acids undergo acyl substitution reactions such as esterification and amidation.^[7] Beyond fundamental chemistry, carboxylates are industrially significant in the production of soaps (as alkali metal salts of fatty acids), polymers like polyacrylates, and pharmaceuticals, where their ionizable nature aids in drug delivery and bioavailability.^[8] In environmental science, carboxylate groups in natural organic matter influence metal speciation, nutrient cycling, and pollutant binding in soils and waters.^[9] Spectroscopic properties, such as asymmetric C-O stretching vibrations around 1550-1650 cm⁻¹, are diagnostic for identifying carboxylates in vibrational spectra, underscoring their analytical importance.^[10]

Definition and Nomenclature

Definition

A carboxylate is the anion formed by the deprotonation of a carboxylic acid, acting as the conjugate base in acid-base equilibria.^[11] It plays a central role in organic and biochemical processes, including as a key intermediate in metabolic pathways and coordination chemistry.^[11] The general formula for the carboxylate ion is RCOO⁻, where R denotes an organic substituent such as an alkyl (e.g., methyl in acetate) or aryl group.^[11] This structure arises from the loss of the acidic proton from the corresponding carboxylic acid, RCOOH.^[11] Carboxylates were first identified in the 19th century through investigations of their metal salts, such as sodium acetate, which was synthesized by French chemist Michel Eugène Chevreul in 1814 via the reaction of acetic acid with sodium carbonate.^[12] These early studies laid the groundwork for understanding carboxylate salts as stable ionic compounds.^[12] At its core, the carboxylate ion consists of a central carbon atom double-bonded to one oxygen and single-bonded to another oxygen bearing a negative charge, forming the characteristic -COO⁻ functional group.^[11] This electronic arrangement contributes to the ion's stability through resonance delocalization of the negative charge between the two oxygen atoms.^[11]

Nomenclature

The nomenclature of carboxylate ions follows the International Union of Pure and Applied Chemistry (IUPAC) recommendations, which derive the name of the anion directly from the corresponding carboxylic acid by replacing the suffix "-oic acid" with "-oate".^[13] For example, the anion derived from ethanoic acid (CH₃COOH) is named ethanoate (CH₃COO⁻).^[13] This systematic approach ensures consistency for both aliphatic and aromatic carboxylates, with the parent chain selected as the longest continuous carbon chain including the carboxylate group, numbered starting from the carbon attached to the oxygen atoms.^[13] For carboxylate salts, the name combines the cation followed by the name of the anion, adhering to conventions for ionic compounds.^[14] For instance, the sodium salt of ethanoic acid is sodium ethanoate (CH₃COONa).^[14] In cases involving polyvalent cations or multiple carboxylate groups, the stoichiometry is indicated by numerical prefixes if necessary, but simple monovalent salts use the basic cation-anion format.^[14] IUPAC retains certain trivial names for widespread use alongside systematic nomenclature, particularly for simple carboxylates.^[13] Notable examples include acetate for CH₃COO⁻ (from acetic acid) and benzoate for C₆H₅COO⁻ (from benzoic acid), which are accepted in general and preferred in some contexts.^[13] These retained names simplify communication but are not used for generating names of more complex derivatives. When the R group in the general formula RCOO⁻ is substituted, the IUPAC name incorporates prefixes for substituents with appropriate locants based on the lowest possible numbers for the chain.^[13] For example, the anion from 2-methylpropanoic acid is named 2-methylpropanoate, where the branch is indicated by the locant and prefix before the parent chain name.^[13] Aromatic substituents follow similar rules, with the carboxylate attached to the ring named as benzoate derivatives if substituted on the benzene ring (e.g., 4-methylbenzoate).^[13] This substituent nomenclature maintains clarity and avoids ambiguity in identifying the principal functional group.^[13]

Structure and Properties

Molecular Geometry

The carboxylate ion, RCOO⁻, features a central carbon atom that is sp² hybridized, resulting in a trigonal planar geometry around this atom with bond angles approximately 120°.^[15] This hybridization arises from the overlap of one s and two p orbitals on the carbon, forming three sp² hybrid orbitals that accommodate sigma bonds to the R group and the two oxygen atoms, while the remaining p orbital participates in pi bonding.^[16] According to the VSEPR model, the COO⁻ group can be described as having three electron domains around the central carbon (two C-O sigma bonds and one C-R sigma bond), corresponding to an AX₃ configuration with no lone pairs on the carbon, which reinforces the trigonal planar arrangement.^[15] The two C-O bonds are equivalent in length, typically ranging from 1.25 to 1.30 Å, as observed in structures like the acetate ion where both measure about 1.26 Å; this equivalence stems from resonance stabilization that delocalizes the electrons across the ion (detailed in the Resonance and Bonding section).^[17] The overall molecular shape of the carboxylate ion is influenced by the nature of the R group attached to the central carbon.^[16] For instance, in simple alkyl carboxylates like acetate (R = CH₃), the tetrahedral geometry around the methyl carbon combines with the planar COO⁻ moiety to yield a relatively compact structure, whereas bulkier or unsaturated R groups can introduce steric or conformational variations without altering the core trigonal planar geometry of the carboxylate functional group.^[18]

Resonance and Bonding

The carboxylate ion exhibits resonance delocalization, with two major contributing structures in which the negative charge alternates between the two oxygen atoms. These structures are represented as R–C(=O)–O⁻ ↔ R–C(–O⁻)=O, where the carbon-oxygen bonds switch between single and double bond character.^[19] This resonance arises from the overlap of p-orbitals on the carbon and oxygen atoms, allowing π-electron delocalization across the functional group. The actual structure of the carboxylate ion is a resonance hybrid of these contributors, resulting in equivalent carbon-oxygen bond lengths of approximately 1.27 Å and partial double-bond character for both bonds.^[19] This delocalization distributes the negative charge evenly over the two oxygen atoms, enhancing the ion's stability compared to localized structures. The partial double-bond character strengthens the C-O bonds, influencing reactivity by reducing susceptibility to nucleophilic attack at the carbon while increasing the ion's nucleophilicity at the oxygen atoms. Resonance provides significant stabilization to the carboxylate ion, with an energy of approximately 20 kcal/mol greater than that of the corresponding carboxylic acid due to the equivalence of the contributing forms.^[20] This stabilization energy, estimated at 20-30 kcal/mol relative to non-resonant anions like alkoxides, arises from the lowered energy of the hybrid compared to individual contributors.^[20] In contrast to the carboxylate ion, the carbonyl group in carboxylic acids features a localized C=O double bond (bond length ≈1.20 Å) and a longer C-OH single bond (≈1.34 Å), with less effective resonance delocalization in the neutral molecule.^[19] The greater resonance stabilization in the deprotonated form contributes to the enhanced stability and reduced reactivity of the carboxylate relative to the acid's carbonyl.

Physical Characteristics

Carboxylates, as the conjugate bases of carboxylic acids, exhibit weak basicity, with the pKa of their conjugate acids typically ranging from 4 to 5. This range indicates that carboxylates accept protons relatively reluctantly in aqueous solutions, consistent with their role in buffering systems where they maintain near-neutral pH environments.^[21]^[22] The solubility of carboxylate salts in water is generally high due to their ionic character, which facilitates strong interactions with water molecules through ion-dipole forces. Solubility trends inversely with the size of the organic R group, as longer alkyl chains introduce hydrophobic effects that reduce aqueous miscibility; short-chain salts like sodium acetate are highly soluble (approximately 123 g/100 mL at 20°C), while long-chain examples such as silver stearate are insoluble owing to the combined influence of chain length and counterion properties.^[1]^[23]^[24] Infrared (IR) spectroscopy provides key signatures for carboxylates, with the asymmetric stretching vibration of the COO⁻ group appearing at 1550–1650 cm⁻¹ and the symmetric stretching at 1300–1400 cm⁻¹; these bands arise from the uniform C–O bond lengths influenced by resonance delocalization. Nuclear magnetic resonance (NMR) further reflects this symmetry, as the equivalent oxygen atoms in the carboxylate moiety result in a single ¹H NMR signal for the methyl group in the acetate ion, typically observed as a singlet around 1.9–2.0 ppm in aqueous or deuterated solvents.^[9]^[25]^[26]^[27]

Synthesis Methods

Deprotonation of Carboxylic Acids

The deprotonation of carboxylic acids represents the primary method for generating carboxylate anions through an acid-base reaction. In this process, a carboxylic acid (RCOOH) reacts with a base (B⁻) to yield the carboxylate ion (RCOO⁻) and the conjugate acid (HB), as depicted in the equation:

\ce{RCOOH + B^- -> RCOO^- + HB}

Here, R denotes an organic substituent such as an alkyl or aryl group, and B⁻ is typically a strong base like the hydroxide ion (OH⁻) or an alkoxide ion (RO⁻). This reaction is straightforward and widely employed in laboratory and industrial settings to produce water-soluble carboxylate salts.^[28] Common reagents for deprotonation include sodium hydroxide (NaOH) and sodium bicarbonate (NaHCO₃), which facilitate the formation of alkali metal carboxylate salts. NaOH, a strong base, fully deprotonates carboxylic acids to form sodium carboxylates (RCOONa), while NaHCO₃, a milder base, is selective for acids with pKa values below approximately 6.3, producing carbon dioxide and water as byproducts. A practical application is in soap production, where fatty acids obtained from the hydrolysis of animal or vegetable fats are deprotonated with NaOH to yield sodium carboxylate salts, which serve as the active cleansing agents in soap..pdf)^[29]^[30] The equilibrium of the deprotonation reaction is primarily driven by the difference in pKa values between the carboxylic acid and the conjugate acid of the base. Carboxylic acids generally exhibit pKa values in the range of 4 to 5, allowing bases whose conjugate acids have higher pKa values—such as water (pKa 15.7) for OH⁻ or carbonic acid (pKa 6.3) for HCO₃⁻—to shift the equilibrium toward the deprotonated carboxylate form. As noted in the physical characteristics section, the pKa of acetic acid, for instance, is 4.76, underscoring the acidity that enables efficient deprotonation under mildly basic conditions.^[28]^[31] The discovery and characterization of carboxylate salts played a pivotal role in early organic chemistry during the 1800s, particularly through studies on acetates and other simple carboxylates. French chemist Michel Eugène Chevreul's investigations around 1816 into the saponification of fats with alkalis led to the isolation and identification of fatty acid salts, marking a foundational advancement in understanding carboxylate chemistry and contributing to the development of systematic organic analysis.^[32]

From Esters and Other Derivatives

One common method for synthesizing carboxylate salts involves the saponification of esters, where an ester reacts with a strong base such as sodium hydroxide to produce the corresponding carboxylate salt and an alcohol byproduct. For instance, methyl acetate undergoes saponification with NaOH to yield sodium acetate and methanol, a process that proceeds via nucleophilic acyl substitution under basic conditions.^[33] This reaction is particularly useful for preparing alkali metal carboxylates from readily available esters and is irreversible due to the formation of the water-soluble carboxylate salt.^[34] Carboxylates can also be obtained through the hydrolysis of more reactive carboxylic acid derivatives, such as acid chlorides and anhydrides. Acid chlorides react vigorously with water to form carboxylic acids, which can then be deprotonated under basic conditions to generate the carboxylate anion; for example, acetyl chloride (CH₃COCl) hydrolyzes to acetic acid and is subsequently converted to acetate ion with base.^[35] Similarly, carboxylic anhydrides undergo hydrolysis to yield two equivalents of carboxylic acid, followed by deprotonation to carboxylates, as seen in the reaction of acetic anhydride with water and base to produce acetate salts.^[36] These transformations exploit the high reactivity of acid chlorides and anhydrides toward nucleophilic attack by water or hydroxide, making them efficient precursors in synthetic routes. Another route to carboxylates involves the basic hydrolysis of nitriles, where a nitrile (RCN) is treated with aqueous base to first form an amide intermediate, which further hydrolyzes to the carboxylate salt and ammonium ion.^[37] Under harsh conditions like heating with NaOH, this stepwise process converts the nitrile carbon to a carboxylate, as in the conversion of acetonitrile (CH₃CN) to sodium acetate.^[36] The reaction requires strong basic conditions to drive the hydrolysis beyond the amide stage, providing a valuable method for extending carbon chains in synthesis.^[38] Organometallic approaches, particularly using Grignard reagents, offer a direct method for carboxylate formation by reacting the organomagnesium compound with carbon dioxide. The Grignard reagent (RMgX) adds to CO₂ to produce a magnesium carboxylate salt (RCOOMgX), which upon acidic workup yields the carboxylic acid but can be isolated as the carboxylate under basic conditions; for example, methylmagnesium bromide reacts with CO₂ to form the acetate precursor.^[39] This carboxylation reaction is widely used to introduce a carboxylic acid functionality with one additional carbon atom from the CO₂ source.

Chemical Reactivity

Alkylation Reactions

Alkylation reactions of carboxylates involve the nucleophilic attack by the carboxylate ion (RCOO⁻) on alkyl halides, leading to the formation of esters through an SN2 mechanism. This process exploits the nucleophilic character of the carboxylate oxygen, enhanced by resonance delocalization of the negative charge across the two oxygen atoms, making it a viable nucleophile for substitution reactions.^[40] The mechanism proceeds via a concerted backside displacement where the carboxylate oxygen bonds to the carbon of the alkyl halide, expelling the halide ion as the leaving group. This is particularly effective with methyl or primary alkyl halides, where steric hindrance is minimal, allowing for clean SN2 substitution. A representative example is the reaction of acetate ion with methyl iodide:

\ce{CH3COO^- + CH3I -> CH3COOCH3 + I^-}

This yields methyl acetate in high yield under typical conditions, such as in polar aprotic solvents like DMF or acetone.^[40] The reaction's scope is limited to unhindered electrophiles, as secondary and tertiary alkyl halides lead to competing E2 elimination due to the strong basicity of the carboxylate ion, resulting in low yields of the desired ester. Steric factors further hinder SN2 progression at more substituted centers, with rate studies showing orders of magnitude slower reactions for secondary substrates compared to primary ones. Additionally, the choice of counterion (e.g., sodium or potassium salts) influences solubility and reactivity, often requiring phase-transfer catalysis for optimal efficiency in biphasic systems.^[41] In applications, this method serves as a complementary route to ester synthesis, particularly useful when Fischer esterification is impractical, such as with sensitive alcohols or when direct access to alkyl halides is available. It is employed in laboratory-scale preparations of simple esters and has been adapted for polymer-supported carboxylates to facilitate purification in combinatorial synthesis. Historically, such alkylations have been key in building ester linkages in natural product analogs, though industrial preference leans toward more scalable alternatives due to halide waste.^[40]^[41]

Acyl Substitution Reactions

Carboxylate ions (RCOO⁻) act as nucleophiles in acyl substitution reactions, targeting the carbonyl carbon of activated acyl derivatives such as acid chlorides to form mixed carboxylic anhydrides. This process follows a classic addition-elimination mechanism: the oxygen of the carboxylate adds to the electrophilic carbonyl carbon of the acid chloride, generating a tetrahedral intermediate; subsequent elimination of the chloride ion reforms the carbonyl, yielding the mixed anhydride (RCOO-COR').^[42] The reaction is efficient due to the excellent leaving group ability of chloride and the moderate nucleophilicity of carboxylates, typically proceeding under mild conditions in aprotic solvents.^[43] A representative equation is:

\text{RCOO}^- + \text{R'COCl} \rightarrow \text{RCOO-COR'} + \text{Cl}^-

This substitution highlights the preference for activated electrophiles, as carboxylates generally do not react with unactivated carbonyls like ketones. For instance, acetate ion does not undergo addition to acetone under standard conditions (CH₃COO⁻ + (CH₃)₂CO → no reaction), underscoring the need for electron-withdrawing activation to lower the carbonyl's LUMO energy and facilitate nucleophilic attack.^[44] With sufficiently activated acyl groups, however, such as in acyl imidazolides or other derivatives, substitution proceeds readily.^[45] Variants of acyl substitution include carboxylate-catalyzed transesterification, where the carboxylate facilitates exchange of alkoxy groups in esters, often via coordination with metal ions like zinc to enhance catalytic activity. In these processes, the carboxylate initiates nucleophilic attack on the ester carbonyl, forming a transient acyl carboxylate intermediate that exchanges with an alcohol nucleophile.^[46] Such mechanisms are particularly relevant in biodiesel production, where metal carboxylates promote efficient transesterification of triglycerides.^[47] In peptide synthesis, mixed anhydrides derived from carboxylates and acid chlorides (or chloroformates) play a crucial role in activating the C-terminal carboxylate of an amino acid for nucleophilic attack by the N-terminal amine of another, enabling selective amide bond formation without racemization under controlled conditions.^[45] This activation strategy, pioneered in the mid-20th century, remains a cornerstone for assembling polypeptides. The nucleophilicity of carboxylates in these reactions is modulated by their basicity, with more basic carboxylates exhibiting higher reactivity toward electrophiles.^[48]

Reduction Reactions

Reduction of carboxylate salts to primary alcohols is commonly achieved using lithium aluminum hydride (LiAlH₄) in anhydrous solvents such as diethyl ether or tetrahydrofuran (THF). The reaction involves the addition of the carboxylate salt to a suspension of LiAlH₄ at low temperature, followed by warming and subsequent aqueous workup with acidification to liberate the alcohol product. This method, first demonstrated in seminal work on hydride reductions, transforms the carboxylate group into a primary alcohol with high efficiency, requiring excess LiAlH₄ to account for the stepwise hydride delivery.^[49] The overall transformation can be represented by the balanced equation:

\ce{RCOO^- + 4[H] -> RCH2OH + OH^-}

Here, four hydride equivalents are incorporated, with the mechanism proceeding through sequential nucleophilic additions to the carbonyl carbon, elimination of oxide intermediates, and final protonation during workup. Representative examples include the conversion of sodium acetate to ethanol or sodium benzoate to benzyl alcohol, yielding primary alcohols in good isolated yields after purification.^[50] The resonance stabilization in the carboxylate ion delocalizes the negative charge across two oxygen atoms, rendering the carbonyl carbon less electrophilic and more resistant to reduction by milder agents like sodium borohydride (NaBH₄). Consequently, LiAlH₄'s high reactivity is essential to overcome this barrier.^[50]

Applications and Examples

Industrial Uses

Carboxylates derived from fatty acids, such as sodium stearate, play a central role in the manufacture of soaps and detergents as anionic surfactants. These compounds lower surface tension and promote the emulsification of oils and greases in aqueous solutions, enabling effective cleaning in household and industrial settings. Sodium stearate, the sodium salt of stearic acid, is particularly valued for imparting solidity and lather to bar soaps, with its amphiphilic structure facilitating dirt removal through micelle formation.^[51]^[52] In the food industry, acetate carboxylates like calcium acetate function as preservatives and processing aids, particularly in baked goods. Calcium acetate (E263) extends shelf life by inhibiting mold and bacterial growth while improving dough conditioning and texture in products such as bread and pastries. It also stabilizes pH to prevent spoilage, with regulatory approval under GMP by Codex Alimentarius and up to 0.5% as per FDA GRAS Notice (as of 2024) in baked items.^[53]^[54]^[55] Polyacrylate polymers, synthesized from carboxylate monomers such as sodium acrylate, are key components in superabsorbent materials for industrial applications. These sodium salts of acrylic acid enable high water retention through ionic swelling, absorbing hundreds of times their weight in liquid, which is essential for products like disposable hygiene items and agricultural hydrogels. The carboxylate groups' electrostatic repulsion in neutralized form drives the polymer's expansion in aqueous environments.^[56]^[57] Carboxylates including acetates and citrates serve as pH buffers in industrial manufacturing, particularly in food processing and pharmaceuticals, to maintain optimal conditions and prevent reactions sensitive to acidity changes. Citric acid, with pKa values of 3.13, 4.76, and 6.40, resists pH shifts in formulations like beverages and lyophilized drugs, while acetate buffers (pKa 4.76) stabilize solutions in chemical production. Their use in these sectors leverages the weak acid-base equilibrium of carboxylate groups for consistent process control.^[58]^[59]

Biological Significance

Carboxylate groups serve essential roles in biochemistry, particularly through their presence in amino acid side chains that enable protein structure, enzymatic catalysis, and metal ion coordination. In aspartate and glutamate, the carboxylate moieties (from their respective side chains) are deprotonated at physiological pH, allowing them to form hydrogen bonds and salt bridges that stabilize protein folds and facilitate substrate binding in enzymes. For instance, these carboxylates often participate in the 2-His-1-carboxylate facial triad motif, coordinating non-heme iron in oxygenases and other metalloenzymes to support catalytic activity.^[60] Additionally, the negative charge of these groups influences protein pKa values and can mimic phosphorylation sites, aiding in regulatory mechanisms like signal transduction.^[61] As metabolic intermediates, carboxylates are integral to energy production and biosynthesis pathways. Acetate, a simple carboxylate ion, is activated to acetyl-CoA by acetyl-CoA synthetase and enters the tricarboxylic acid (TCA) cycle, fueling ATP generation and providing carbon skeletons for fatty acid synthesis in various tissues.^[62] Citrate, a tricarboxylate anion, acts as a central hub in the TCA cycle, where it is formed from acetyl-CoA and oxaloacetate by citrate synthase; beyond energy metabolism, it regulates cytosolic processes like fatty acid synthesis by exporting acetyl-CoA equivalents across mitochondrial membranes.^[63] In neuronal signaling, carboxylate groups contribute to ion channel modulation and neurotransmission. Glutamate, the primary excitatory neurotransmitter, features two carboxylate groups that are critical for binding to ionotropic receptors like NMDA and AMPA, enabling synaptic plasticity and fast excitatory transmission through electrostatic interactions with receptor pockets.^[64] These anionic sites also influence receptor gating kinetics by funneling the ligand into binding sites via interactions with positively charged residues.^[65] Carboxylates play a key role in metal chelation within proteins, enhancing stability and function. In heme-containing proteins, the propionate carboxylate side chains of heme b coordinate with protein residues to anchor the cofactor and promote electron transfer in cytochromes and hemoglobin.^[66] Similarly, in calcium-binding proteins such as calmodulin and vitamin K-dependent factors, aspartate and glutamate carboxylates form coordination spheres around Ca²⁺ ions, often supplemented by γ-carboxyglutamic acid residues for high-affinity binding that regulates processes like blood coagulation and muscle contraction.^[67]^[68]

Notable Compounds

The acetate ion (CH_3COO^-) is the simplest carboxylate anion, serving as the conjugate base of acetic acid and playing a key role as a human metabolite involved in biosynthetic pathways such as fatty acid synthesis.^[69] Its common salt, sodium acetate (CH_3COONa), is widely used as a buffering agent in biochemical and industrial processes due to its solubility and pH-stabilizing properties. The benzoate ion (C_6H_5COO^-) is the carboxylate derived from benzoic acid, with its sodium salt (C_6H_5COONa) approved by the FDA as a food preservative (E211) that effectively inhibits the growth of bacteria, yeast, and molds in acidic environments like soft drinks and sauces. This antimicrobial action stems from its ability to disrupt microbial cell processes, making it one of the most commonly used preservatives in the food industry.^[70] The lactate ion (CH_3CH(OH)COO^-), or 2-hydroxypropanoate, is a vital intermediate in cellular metabolism, particularly in skeletal muscle where it accumulates during anaerobic glycolysis to regenerate NAD^+ for continued ATP production under oxygen-limited conditions.^[71] Elevated lactate levels serve as a biomarker for metabolic stress in critically ill patients, reflecting an imbalance in oxygen supply and demand.^[71] Common salts include sodium lactate, utilized in medical solutions for electrolyte balance and acid-base correction.^[72] Ethylenediaminetetraacetic acid (EDTA) is a prominent polyaminocarboxylate featuring four carboxylate groups attached to an ethylenediamine backbone, enabling it to function as a hexadentate ligand that forms stable chelates with metal ions through multiple coordination sites.^[73] In its deprotonated form (ethylenediaminetetraacetate ion), EDTA is employed in chelation therapy to bind and remove toxic heavy metals like lead from the body, as well as in industrial applications for water softening by sequestering calcium and magnesium ions.^[73] Its polydentate nature ensures high thermodynamic stability in metal complexes, with formation constants often exceeding $10^{16} for divalent cations.^[74]

References

[1]
Carboxylic Acid Reactivity - MSU chemistry
Both the carboxyl group and the carboxylate anion are stabilized by resonance, but the stabilization of the anion is much greater than that of the neutral ...
[2]
Functional Groups - FSU Chemistry & Biochemistry
Carboxylate ion or salt 1. Carboxylate ions are the conjugate bases of carboxylic acids, ie. the deprotonated carboxylic acid. Carboxylate ions can be shown ...
[3]
Chapter 19: Carboxylic Acids - Oregon State University
Feb 7, 2020 · Carboxylic acids are, by definition, Brønsted acids that can donate a proton to ther species with lone pairs. Ionization of RCOOH in water.
[4]
Carboxylic Acids, Esters - CHE 120 - Introduction to Organic Chemistry
Aug 18, 2025 · The anion formed when a carboxylic acid dissociates is called the carboxylate anion (RCOO −). Whether soluble in water or not, carboxylic ...
[5]
Molecular Orientation of Carboxylate Anions at the Water–Air ...
The carboxylate anion group plays an important role in many (bio)chemical systems and polymeric materials. In this work, we study the orientation of ...
[6]
Derivatives of Carboxylic Acids - MSU chemistry
Reactions of this kind are important synthetic transformations, because they permit simple starting compounds to be joined to form more complex structures.
[7]
[PDF] Structural environments of carboxyl groups in natural organic ...
Carboxyls play an important role in the chemistry of natural organic molecules (NOM) in the environment, and their behavior is dependent on local structural ...
[8]
[PDF] Carboxylic Acid Structure and Chemistry: Part 2
Carboxylic acids can undergo ionization, salt formation, nucleophilic attack at the carbonyl or adjacent carbon, and decarboxylation. They ionize in basic ...
[9]
Hydration effects on the vibrational properties of carboxylates
Jun 10, 2023 · The presence of carboxyl groups in a molecule delivers an affinity to metal cations and a sensitivity to the chemical environment, ...
[10]
11.2: The Structures of Carboxylic Acids and ... - Chemistry LibreTexts
Aug 29, 2014 · Carboxylic acids are named such because they can donate a hydrogen to produce a carboxylate ion. The factors which affect the acidity of ...
[11]
Sodium acetate 127-09-3 wiki - Guidechem
Sodium acetate was first synthesized in the early 19th century by the French ... Industrially, sodium acetate is prepared from glacial acetic acid and sodium ...
[12]
[PDF] Brief Guide to the Nomenclature of Organic Chemistry - IUPAC
The International Union of Pure and Applied Chemistry (IUPAC) provides recommendations on many aspects of nomenclature.1 The basics of organic nomenclature are ...
[13]
Rule C-461 Salts of Carboxylic Acids and Their Derivatives
461.1 - Neutral salts of carboxylic, amic, imidic, carboximidic, hydroxamic, carbohydroxamic, etc., acids are named by citing the cation(s) and then the anion.
[14]
20.2 Structure and Properties of Carboxylic Acids
Nov 23, 2023 · However, in the structure of a carboxylic acid the C− O bond (1.20 Å) is shorter than the C− OH bond (1.34 Å).
[15]
18.3: Some Chemical Properties of Carboxylic Acids
Jul 31, 2021 · ... kcal mol − 1 . The stabilization energy of the carboxylate anion is substantially greater than that of the acid, because the anion is a ...
[16]
[PDF] values to know 1. Protonated carbonyl pKa
Carboxylic acid pKa = 4-5. 4. Ammonium ion pKa = 9-10. 5. Phenol pKa = 10. 6. Thiol pKa = 10. 7. Alcohol pKa = 16-18. 8. Water pKa = 15.7. 9. Amide pKa = 18. 10 ...
[17]
Chapter 19 notes
Acidity of Carboxylic Acids. stronger acids than alcohols pKa ~ 5 (alcohol pKa values about 15-18 ) · the carboxylate anion is stabilized by resonance.
[18]
Sodium Acetate | CH3COONa | CID 517045 - PubChem - NIH
Sodium Acetate is the trihydrate sodium salt of acetic acid with alkalinizing, diuretic and electrolyte replacement properties. Following absorption, sodium ...Missing: discovery | Show results with:discovery
[19]
US3458544A - Preparation of silver salts of organic carboxylic acids
The water insoluble silver salt forms as a precipitate at the interface of the two immiscible phases and is recovered, usually by settling, filtration, washing ...
[20]
The Carbonyl Group, Part V: Carboxylates—Coming Clean
May 1, 2018 · Carboxylates are made by reacting carboxylic acids with strong bases such as inorganic hydroxides. The resultant salts are commonly used as cleansers.
[21]
Intro to Resonance In Organic Chemistry
Nov 23, 2011 · What this means is that the true structure of the acetate ion (and the allyl carbocation) is a “hybrid” of two resonance forms. We use a special ...
[22]
Sodium acetate(127-09-3) 1H NMR spectrum - ChemicalBook
Sodium acetate(127-09-3) 1H NMR. Product NameSodium acetate. CAS127-09-3. Molecular FormulaC2H3NaO2. Molecular Weight ...
[23]
[PDF] Carboxylic Acids
The carbon is sp2 hybridized, and the O-H bond lies in the plane described by the sp2 carbon, eclipsing the C=O double bond. This unexpected geometric ...
[24]
CH 318N: Professor Nathan L
Because carboxylic acids are stronger acids than phenols, carboxylic acids can be deprotonated with sodium bicarbonate (NaHCO3) to a greater extent than phenol.
[25]
Reactivity in Chemistry - csbsju
In the old days, soap would be made by taking animal fats and mixing them with lye, breaking the ester linkages in the fats to make carboxylate salts. Figure ...<|control11|><|separator|>
[26]
[PDF] Carboxylic Acid Acidity - Bluefield Esports
... carboxylic acid, the equilibrium favors the protonated form (RCOOH). At a pH significantly above the pKa, the equilibrium favors the deprotonated form (RCOO⁻).
[27]
CH105: Chapter 6 - Natural Products & Organic Chemistry
Around 1816 Michel Chevreul started a study of soaps made from various fats and alkalis. This process is called saponification. You will notice that the ester ...
[28]
Chapter 17 - Carboxyl Derivatives
base-catalyzed hydrolysis is often called saponification (soap-making) saponification is irreversible because a carboxylate salt is formed. soaps are the salts ...
[29]
LON-CAPA EsterCondensations
Saponification of Esters. The formation of carboxylic acids by treatment of esters with sodium hydroxide is known as saponification. Equation 1 summarizes ...
[30]
[PDF] Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 20.1
Mechanism occurs in two stages. The first is addition of the nucleophile to the carbonyl carbon to form a tetrahedral intermediate. The second stage in collapse ...
[31]
[PDF] Carboxylic acid Derivatives
Carboxylic acid derivatives are described as compounds that can be converted to carboxylic acids via simple acidic or basic hydrolysis. The most important acid ...
[32]
Carboxylic Acid Derivatives - MSU chemistry
Hydrolysis of nitriles to carboxylic acids was described earlier, and requires reaction conditions (catalysts and heat) similar to those needed to hydrolyze ...
[33]
[PDF] Preparation of Nitriles
O H + + Page 8 Hydrolysis of Nitriles In basic solution the carboxylic acid product is deprotonated to give a carboxylate ion. O, heat 2. H+ Page 11 Hydrolysis ...
[34]
[PDF] Chapter 19: Carboxylic Acids
Conversion of an alkyl or aryl Grignard reagent to a carboxylic acid with an addition carbon (the CO2H group). The CO2H group is derived from CO2. R-Br. Mg(0).
[35]
https://www.vanderbilt.edu/AnS/Chemistry/Rizzo/Chem220b/Ch20.pdf
[36]
21.6 Chemistry of Esters - NC State University Libraries
Thus, carboxylic acids are converted directly into esters by SN2 reaction of a carboxylate ion with a primary alkyl halide or by Fischer esterification of a ...
[37]
Esterification by alkylation of carboxylate salts. Influence of steric ...
Esterification by alkylation of carboxylate salts. Influence of steric factors and other parameters on reaction rates.
[38]
Nucleophilic Acyl Substitution (With Negatively Charged Nucleophiles)
May 6, 2011 · In the first, acid chlorides react with carboxylates (the conjugate base of carboxylic acids, acting as a nucleophile here) to give an anhydride ...
[39]
Reactions of Acid Chlorides (ROCl) with Nucleophiles
Carboxylate ion is a good nucleophile and reacts readily with acid chloride, forming carboxylic acid anhydrides: One advantage of preparing anhydrides by this ...
[40]
Preparation of Peptides Using Mixed Carboxylic Acid Anhydrides
The mechanism of the complex reactions that may take place between protein carboxyl groups and hot mixtures of acetic anhydride and pyridine in the acetic ...
[41]
Reaction mechanism study on transesterification in synthesis of ...
Oct 15, 2022 · The mechanism of transesterification catalyzed by zinc(II) carboxylate was proposed. The energetically favored catalytic pathway was established by DFT ...
[42]
Efficient One-Step Conversion of a Low-Grade Vegetable Oil to ...
Jan 14, 2021 · In this study, the catalytic performance of a three-dimensional (3D) Zn(II)-based carboxylate MOF (hereafter denoted as Zn3(BTC)2) is examined ...
[43]
[7] Coupling reagents and activation - ScienceDirect.com
The controlled formation of a peptide bond (the so called coupling reaction) between two amino acids requires activation of the carboxyl group of one for facile ...
[44]
Reduction of Organic Compounds by Lithium Aluminum Hydride. II ...
Lithium aminoborohydrides: Powerful, selective, air-stable reducing agents. Organic Process Research & Development 2006, 10 (5) , 959-970.
[45]
Heterogeneously Catalyzed Carboxylic Acid Hydrogenation to ...
Sep 14, 2022 · This critical review discusses the synthesis of alcohols via hydrogenation of carboxylic acids promoted by heterogeneous metal catalysis.
[46]
Sodium stearate - American Chemical Society
Nov 9, 2020 · Sodium stearate is the most common fatty acid salt in soaps, derived from stearic acid, and used in cosmetics and other products.
[47]
Applications of Sodium Stearate | PISHRO CHEM
Aug 8, 2023 · Sodium stearate is a primary component in many soap bars, granting them the firm texture and helping them lather when mixed with water.
[48]
Calcium Acetate: Food Additive with Multiple Benefits
Feb 27, 2025 · Calcium Acetate (E263) enhances food texture, extends shelf life, and maintains pH stability in baked goods, dairy, and confectionery.Missing: carboxylates | Show results with:carboxylates
[49]
GSFA Online Food Additive Details for Calcium acetate
Calcium acetate is a food additive that is included in Table 3, and as such may be used in the following foods under the conditions of good manufacturing ...
[50]
Giving superabsorbent polymers a second life as pressure-sensitive ...
Jul 26, 2021 · Sodium polyacrylate-based superabsorbent materials used in disposable diapers and feminine hygiene products have been challenging to recycle ...<|separator|>
[51]
[PDF] Super-Absorbent Polymer: A Review on the Characteristics and ...
The principal monomer used in the manufacturing of superabsorbent polymer is acrylic acid. Acrylic acid is made by the oxidation of propene inn two step. First, ...
[52]
Citric Acid: A Multifunctional Pharmaceutical Excipient - PMC
Citrate buffers are used extensively in lyophilized products because they usually do not crystallize during the process and remain amorphous, with minimal pH ...
[53]
Breaking old habits: Moving away from commonly used buffers in ...
Jul 10, 2012 · Citric acid is one of the most commonly used buffers (Table 1). It is a trivalent buffer containing three carboxylic acids with pKa of 3.1, 4.8 ...
[54]
Variations of the 2-His-1-carboxylate theme in mononuclear non ...
A facial triad of two histidine side chains and one aspartate or glutamate side chain forms the canonical metal-coordinating motif in the catalytic centers ...
[55]
A mechanism for the evolution of phosphorylation sites - PubMed - NIH
Nov 11, 2011 · The evolution of phosphorylation sites from glutamate and aspartate provides a rationale for why phosphorylation sometimes activates proteins, ...
[56]
Regulation and function of the mammalian tricarboxylic acid cycle
Acetate can function as a source of acetyl-CoA through the activity of acetyl-CoA synthetase (ACSS), which catalyzes the ATP-dependent ligation of acetate and ...Tca Cycle Anaplerosis · Nodes Of Tca Cycle Control · Metabolic Control Of Gene...
[57]
NaCT/SLC13A5 facilitates citrate import and metabolism under ...
Sep 14, 2021 · Citrate lies at a critical node of metabolism, linking tricarboxylic acid metabolism and lipogenesis via acetyl-coenzyme A. Recent studies ...
[58]
Neurotransmitter Funneling Optimizes Glutamate Receptor Kinetics
Jan 3, 2018 · In all but one of the binding trajectories, the carboxyl groups of glutamate were exploited by positively charged side chains at the periphery ...
[59]
Glutamic Acid - an overview | ScienceDirect Topics
The γ-carboxylic acid group of glutamic acid has a pK′ of 4.25 and is ionized at physiological pH. The anionic groups of glutamate (like those of aspartate) ...
[60]
The broad diversity of heme-protein cross-links: An overview
This review presents an overview of the broad diversity of heme-protein cross-links, including Cys/SeCys -heme, Met-heme, His-heme, Trp/Tyr-heme, Glu/Asp-
[61]
Carboxylated calcium-binding proteins and vitamin K - PubMed
Carboxylated calcium-binding proteins and vitamin K. N Engl J Med. 1980 Jun 26;302(26):1460-6. doi: 10.1056/NEJM198006263022608.
[62]
Interaction of metal ions with carboxylic and carboxamide groups in ...
An analysis of the geometry of metal binding by carboxylic and carboxamide groups in proteins is presented. Most of the ligands are from aspartic and glutamic ...
[63]
Acetate | C2H3O2- | CID 175 - PubChem - NIH
Acetate is a monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of acetic acid. It has a role as a human metabolite and ...Missing: carboxylate | Show results with:carboxylate
[64]
Sodium Benzoate—Harmfulness and Potential Use in Therapies for ...
Apr 2, 2022 · It inhibits the growth of bacteria, yeast, and mold [6]. Sodium benzoate was approved as the first of all food preservatives by the Food and ...
[65]
Lactate
### Summary of Lactate Ion from PubChem
[66]
[PDF] Page 1 of 7 - accessdata.fda.gov
Lactate is slowly metabolized to carbon dioxide and water, accepting one hydrogen ion and resulting in the formation of bicarbonate for the lactate consumed. ...
[67]
Ethylenediaminetetraacetic Acid | C10H16N2O8 | CID 6049
Ethylenediamine tetraacetic acid is a colorless crystalline solid. It is slightly soluble in water. The primary hazard is the threat to the environment.
[68]
Lanthanide complexes with polyaminopolycarboxylates as ...
Paramagnetic lanthanide complexes with PAPC ligands. Lanthanide complexes with EDTA. We can mention that the EDTA-ligand is used to treat heavy metal ...