Carboxylic acid

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO₂H, sometimes as R−C(O)OH with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Carboxylic acids are commonly identified by their trivial names. They often have the suffix -ic acid. IUPAC-recommended names also exist; in this system, carboxylic acids have an -oic acid suffix. For example, butyric acid (CH₃CH₂CH₂CO₂H) is butanoic acid by IUPAC guidelines. For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid. Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another parent structure, such as 2-carboxyfuran.

The carboxylate anion (R−COO⁻ or R−CO−2) of a carboxylic acid is usually named with the suffix -ate, in keeping with the general pattern of -ic acid and -ate for a conjugate acid and its conjugate base, respectively. For example, the conjugate base of acetic acid is acetate.

Carbonic acid, which occurs in bicarbonate buffer systems in nature, is not generally classed as one of the carboxylic acids, despite it having a moiety that looks like a COOH group.

Carboxylic acids are polar. Because they are both hydrogen-bond acceptors (the carbonyl −C(=O)−) and hydrogen-bond donors (the hydroxyl −OH), they also participate in hydrogen bonding. Together, the hydroxyl and carbonyl group form the functional group carboxyl. Carboxylic acids usually exist as dimers in nonpolar media due to their tendency to "self-associate". Smaller carboxylic acids (1 to 5 carbons) are soluble in water, whereas bigger carboxylic acids have limited solubility due to the increasing hydrophobic nature of the alkyl chain. These longer chain acids tend to be soluble in less-polar solvents such as ethers and alcohols. Aqueous sodium hydroxide and carboxylic acids, even hydrophobic ones, react to yield water-soluble sodium salts. For example, enanthic acid has a low solubility in water (0.2 g/L), but its sodium salt is very soluble in water.

Carboxylic acids tend to have higher boiling points than water, because of their greater surface areas and their tendency to form stabilized dimers through hydrogen bonds. For boiling to occur, either the dimer bonds must be broken or the entire dimer arrangement must be vaporized, increasing the enthalpy of vaporization requirements significantly.^{[citation needed]}

Carboxylic acids are Brønsted–Lowry acids because they are proton (H⁺) donors. They are the most common type of organic acid.

Carboxylic acids are typically weak acids, meaning that they only partially dissociate into [H₃O]⁺ cations and R−CO−2 anions in neutral aqueous solution. For example, at room temperature, in a 1-molar solution of acetic acid, only 0.001% of the acid are dissociated (i.e. 10⁻⁵ moles out of 1 mol). Electron-withdrawing substituents such as trifluoromethyl (−CF₃) give stronger acids (the pK_a of acetic acid is 4.76 whereas trifluoroacetic acid, with a trifluoromethyl substituent, has a pK_a of 0.23). Electron-donating substituents give weaker acids (the pK_a of formic acid is 3.75 whereas acetic acid, with a methyl substituent, has a pK_a of 4.76)