Name: how bonding affects acid strength
Uploaded: 2020-09-24T15:06:51.000Z
Duration: 3 min 5 s
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Acid Strength and Molecular Structure

O ácido clorídrico é um ácido forte, enquanto que o ácido hidrofluorídrico é um ácido fraco. Mas o que determina a sua força, a força dos ácidos binários, com apenas dois elementos, é determinada pelo vínculo de polaridade e energia. Um ácido com uma ligação energética mais elevada tem uma ligação mais forte e, por conseguinte é um ácido mais fraco.Comparando os ácidos de um grupo, a ligação num ácido fraco, como o ácido fluorídrico, é mais difícil de quebrar, por isso o ácido é menos provável de doar prótons. Em contraste, um ácido com menor ligação energética tem uma ligação mais fraca e, por conseguinte é um ácido mais forte. Por exemplo, a ligação num ácido forte, como o ácido clorídrico, quebra mais facilmente e doa mais prótons do que o ácido fluorídrico.Uma ligação, como aquela no ácido clorídrico, é polar quando um átomo é mais eletronegativo do que o outro átomo. Um composto pode agir como um ácido quando o átomo ligado ao hidrogénio tem uma maior eletronegatividade do que o hidrogénio. O átomo irá possuir uma carga parcialmente negativa, permitindo que o hidrogénio tenha uma carga parcialmente positiva para que possa ser libertado como um próton.Um ácido com maior ligação de polaridade tem uma ligação mais fraca e, por conseguinte é um ácido mais forte. Comparando os compostos ao longo de um período, o ácido clorídrico é mais forte do que o sulfureto de hidrogénio uma vez que o cloro é mais eletronegativo do que o enxofre e, portanto, liberta prótons mais facilmente. Se o hidrogénio tiver uma maior eletronegatividade do que o outro átomo, a molécula não pode doar prótons e, portanto, pode não agir como um ácido.Os oxiácidos são ácidos onde um OH é anexado a um terceiro átomo que é mais eletronegativo do que o hidrogénio. A força de um oxiácido depende sobre a eletronegatividade e o número de oxigénios anexado ao terceiro átomo. Quanto mais alto a eletronegatividade do átomo, quanto mais polariza, mais enfraquece a ligação entre o oxigénio e o hidrogénio.Se o átomo central estiver ligado a átomos de oxigénio adicionais, aumenta ainda mais a polaridade da ligação entre o oxigénio e o hidrogénio. Por exemplo, o ácido perclórico com três átomos de oxigénio adicional é mais forte que o ácido clorídrico com dois átomos de oxigénio adicionais. O ácido clorídrico, que é mais forte do que o ácido cloroso, tem apenas um oxigénio adicional e o ácido hipocloroso, não tem nenhum átomo de oxigénio adicional.Os ácidos carboxílicos são ácidos fracos que contêm um grupo carboxil. O segundo átomo de oxigénio faz a ligação oxigénio-hidrogénio mais polar, e por conseguinte permite a molécula para doar um próton. O ácido acético e o ácido fórmico são exemplos de ácidos carboxílicos.

força e estrutura molecular de Ácidos

Ácidos e Bases Binários
Na ausência de qualquer efeito de nivelamento, a força ácida dos compostos binários de hidrogénio com não metais (A) aumenta à medida que a força da ligação H-A diminui indo para baixo em um grupo na tabela periódica. Para o grupo 17, a ordem de aumento da acidez é HF < HCl < HBr < H. Da mesma forma, para o grupo 16, a ordem de aumento da força de acidez é H2O < H2S < H2Se < H2Te. Ao longo de uma linha na tabela periódica, a força ácida dos compostos binários de hidrogénio aumenta com o aumento da eletronegatividade do átomo não metálico, porque a polaridade da ligação H-A aumenta. Assim, a ordem de aumento da acidez (para remoção de um protão) na segunda linha éCH4 < NH3 < H2O < HF; na terceira linha, é SiH4 < PH3 < H2S < HCl.
Ácidos e Bases Ternários
Compostos ternários constituidos por hidrogénio, oxigénio, e algum terceiro elemento (“E”) podem ser estruturados conforme ilustrado na imagem abaixo. Nestes compostos, o átomo central de E está ligado a um ou mais átomos de O, e pelo menos um dos átomos de O também está ligado a um átomo de H, correspondendo à fórmula molecular geral OmE(OH)n. Estes compostos podem ser ácidos, básicos, ou anfotéricos, dependendo das propriedades do átomo central E. Exemplos desses compostos incluem ácido sulfúrico, O2S(OH)2, ácido sulfuroso, OS(OH)2, ácido nítrico, O2NOH, ácido perclórico, O3ClOH, hidróxido de alumínio, Al(OH)3, hidróxido de cálcio, Ca(OH)2, e hidróxido de potássio, KOH.
<img alt="Eq1" src="/files/ftp_upload/11406/11406_Figure_1.svg" style="height: 90px;" />
Se o átomo central, E, tiver uma baixa eletronegatividade, a sua atração para eletrões é baixa. Existe pouca tendência para o átomo central formar uma forte ligação covalente com o átomo de oxigénio, e a ligação a entre o elemento e o oxigénio é mais facilmente quebrada do que a ligação b entre o oxigénio e o hidrogénio. Portanto, a ligação a é iónica, iões hidróxido são libertados para a solução, e o material comporta-se como uma base—este é o caso com Ca(OH)2> e KOH. Uma menor eletronegatividade é característica dos elementos mais metálicos; portanto, os elementos metálicos formam hidróxidos iónicos que são, por definição, compostos básicos.
Se, por outro lado, o átomo E tiver uma eletronegatividade relativamente alta, atrai fortemente os eletrões que compartilha com o átomo de oxigénio, criando uma ligação covalente relativamente forte. A ligação oxigénio-hidrogénio, ligação b, é assim enfraquecida porque os eletrões são deslocados para E. A ligação b é polar e liberta prontamente iões de hidrogénio para a solução, pelo que o material comporta-se como um ácido. Eletronegatividades elevadas são características dos elementos mais não metálicos. Assim, elementos não metálicos formam compostos covalentes contendo grupos ácidos −OH, chamados de oxiácidos.
Aumentando do número de oxidação do átomo central E aumenta também a acidez de um oxiácido, pois isso aumenta a atração de E para os eletrões que compartilha com o oxigénio e, assim, enfraquece a ligação O-H. O ácido sulfúrico H2SO4, ou O2S(OH)2 (com um número de oxidação de enxofre de +6) é mais ácido do que o ácido sulfuroso, H2SO3, ou OS(OH)2 (com um número de oxidação de enxofre de +4). Da mesma forma, o ácido nítrico, HNO3, ou O2NOH (número de oxidação N = +5), é mais ácido do que o ácido nitroso, HNO2, ou ONOH (número de oxidação N = +3). Em cada um destes pares, o número de oxidação do átomo central é maior para o ácido mais forte.
Ácidos Carboxílicos
Os ácidos carboxílicos contêm um grupo carboxilo. Os ácidos carboxílicos são ácidos fracos, o que significa que não são 100% ionizados em água.
O ácido carboxílico age como um ácido fraco porque, como no caso dos oxiácidos, o segundo oxigénio ligado ao átomo de carbono aumenta a polaridade da ligação O-H e torna-a mais fraca. Além disso, após a perda do protão, o grupo carboxilo é convertido para o ião carboxilato, que apresenta ressonância. As diferentes estruturas de ressonância estabilizam o ião carboxilato, pois a sua carga negativa é deslocalizada ao longo de vários átomos.
Este texto é adaptado de<a href="https://openstax.org/books/chemistry-2e/pages/14-3-relative-strengths-of-acids-and-bases"> Openstax, Chemistry 2e, Section 14.3: Relative Strengths of Acids and Bases</a> e <a href="https://openstax.org/books/chemistry-2e/pages/20-3-aldehydes-ketones-carboxylic-acids-and-esters">Openstax, Chemistry 2e, Section 20.3 Aldehydes, Ketones, Carboxylic Acids, and Esters</a>.

Força e Estrutura Molecular de Ácidos

Ácidos e Bases Binárias
Na ausência de qualquer efeito de nivelamento, a resistência ácida de compostos binários de hidrogênio com não-metais (A) aumenta à medida que o H-A ...

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TERMOS-CHAVE E CONCEITOS

how bonding affects acid strength

Acid strength depends on bonding, electronegativity, and oxidation number. These factors help explain why some hydrogen compounds act as strong acids, while others behave as weak acids or bases.

For binary acids, which are hydrogen compounds with one other nonmetal, acidity increases as the H-A bond gets weaker down a group. That is why the order for group 17 is HF &lt; HCl &lt; HBr &lt; HI, and for group 16 it is H2O &lt; H2S &lt; H2Se &lt; H2Te. Across a period, acid strength increases as the nonmetal becomes more electronegative because the H-A bond becomes more polar. The second row follows CH4 &lt; NH3 &lt; H2O &lt; HF, and the third row follows SiH4 &lt; PH3 &lt; H2S &lt; HCl.

Ternary acids and bases contain hydrogen, oxygen, and a third element E. Their general form is OmE(OH)n, and they may be acidic, basic, or amphoteric. Examples include sulfuric acid, sulfurous acid, nitric acid, perchloric acid, aluminum hydroxide, calcium hydroxide, and potassium hydroxide.

If E has low electronegativity, it does not hold electrons strongly. In that case, the bond between E and oxygen is more likely to break than the O-H bond, so hydroxide ions are released and the compound acts as a base. This is typical of more metallic elements, which form ionic hydroxides such as Ca(OH)2 and KOH.

If E has high electronegativity, it pulls electron density toward itself. That weakens the O-H bond and makes it easier to release H+ ions, so the compound behaves as an acid. These nonmetal compounds are called oxyacids. A higher oxidation number on E also increases oxyacid strength because it pulls harder on shared electrons. For example, H2SO4 is more acidic than H2SO3, and HNO3 is more acidic than HNO2.

Carboxylic acids also show weak-acid behavior. They contain a carboxyl group, and they are not fully ionized in water. The second oxygen attached to carbon makes the O-H bond more polar and weaker. After the proton leaves, the carboxylate ion is stabilized by resonance, which spreads the negative charge over several atoms.

How Bonding Affects Acid Strength

bronsted-lowry acids and bases

Proton Transfer in Acids and Bases

Acids and bases can be understood through proton transfer. Early scientists described acids by their sour taste, their effect on dyes, and their reaction with limestone, which releases carbon dioxide. Robert Boyle also noted that acid solutions can lose these properties after contact with alkali, or base, solutions. The modern view developed step by step. Humphry Davy showed that hydrogen is the essential part of acids. Joseph Louis Gay-Lussac then described acids as substances that neutralize...

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Water as an Amphiprotic Substance

Water can act as both a Brønsted-Lowry acid and a Brønsted-Lowry base. When hydrogen fluoride dissolves in water, it donates protons to water. This is acid ionization. The products are hydronium ions and fluoride ions. Water can also accept protons from another substance. When pyridine dissolves in water, it accepts a proton from water molecules. This is base ionization. The products are hydroxide ions and pyridinium ions. These reactions show that water can play either role. A substance that...

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pH and pOH in Water

pH and pOH show how hydronium and hydroxide ions behave in water and other aqueous solutions. These ion concentrations are linked by the ion product of water, K w , so when one goes up, the other goes down. Because ion concentrations can differ by huge amounts, a logarithmic scale is used to describe them. pH is defined from the hydronium ion concentration, [H3O+], and pOH is the matching p-function for hydroxide ion concentration. These two values are also connected through the K w...

relative strengths of conjugate acid-base pairs

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How Ka and Kb Show Acid-Base Strength

Brønsted-Lowry acid-base chemistry is based on proton transfer. That idea helps show how the strength of an acid is linked to the strength of its conjugate base, and vice versa. Acid and base strength is measured with ionization constants, Ka and Kb, which tell how far an ionization reaction goes. For the conjugate pair HA and A−, the acid ionizes in water and the base reaction can be written for the partner species. When the two reactions are added, they give the autoionization of water. The...

strong acid and base solutions

Strong Acids, Strong Bases, and pH

Strong acids and strong bases change the pH of a solution by dissociating completely in water. A strong acid produces hydronium ions, which are H3O+ ions, and a strong base produces hydroxide ions, OH-. Because the dissociation is complete, the ion concentration can be found from the starting concentration and the molar ratio. For example, 0.20 M hydrobromic acid dissociates fully in water. It produces 0.20 M hydronium ions and 0.20 M bromide ions. A 0.015 M KOH solution also dissociates...

weak acid solutions

Weak Acid Equilibrium in Water

Weak acid equilibrium in water explains why many acids only partially react when dissolved. Most weak acid molecules stay in their original form, and only a small amount of hydronium ions forms. Weak acids are common in nature. They help create the tangy taste of citrus fruits, the stinging sensation from insect bites, and the smells linked to body odor. Acetic acid is a familiar weak acid. It is the main ingredient in vinegar. Its equation uses a double arrow to show that the reaction with...

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Weak Base pH and Kb Calculations

Weak base pH and Kb calculations show how partially reacting bases change water chemistry. Weak bases produce hydroxide ions when they dissolve by reacting with water molecules. Because the reaction only happens partly, these compounds are classified as weak bases. Weak bases are common in nature and in technology. Ammonia is one major example. Global production of ammonia is typically well over 100 metric tons each year. It is used as an agricultural fertilizer, a starting material for...

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pH of Acid Mixtures

The pH of acid mixtures depends on the acids present, their dissociation constants, and their starting concentrations. When a solution contains two different acids, the pH can be found by choosing the method that fits their relative strengths. This makes acid mixtures a useful case for applying acid-base rules in chemistry. In a mixture of a strong acid and a weak acid, the strong acid dissociates completely and supplies almost all of the hydronium ions in the solution. The weak acid...

ions as acids and bases

Salt Hydrolysis and pH of Solutions

Salt hydrolysis explains why some salt solutions are acidic, basic, or neutral. Salts are ionic compounds made of cations and anions. In water, either ion may react with water through an acid or base ionization reaction. The pH of the solution depends on the relative acid-base strength of the ions in the salt. Ammonium chloride is a good example of an acidic salt. When it dissolves, it separates into ammonium ions and chloride ions. The ammonium ion is the conjugate acid of ammonia, so it can...

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Salt Hydrolysis and pH in Solutions

Salt hydrolysis and pH in solutions depend on the ions released when a salt dissolves. Some ions react with water, while others do not. The balance between the cation and anion helps show whether the solution becomes acidic, basic, or neutral. Salts with pH-neutral anions and cations that produce hydronium ions give acidic solutions with pH below 7. Ammonium nitrate is one example. In NH4NO3, NO3− does not react with water, but NH4+ forms hydronium ions, so the solution is acidic. Other salts...

acid/base strengths and dissociation constants

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Acid and Base Strength in Water

Acid and base strength in water depends on how much a substance ionizes after it dissolves. If ionization is nearly complete, the substance is called strong. If only a small amount ionizes, it is called weak. Weak acids and weak bases are much more common than strong ones. The most common strong acids are HClO4, HCl, HBr, HI, HNO3, and H2SO4. The most common strong bases are LiOH, NaOH, KOH, Ca(OH)2, Sr(OH)2, and Ba(OH)2. These strong acids and bases ionize essentially completely in water. <br...

polyprotic acids

Stepwise Ionization of Polyprotic Acids

Polyprotic acids lose hydrogen ions in steps. The number of ionizable protons in a molecule determines whether an acid is monoprotic, diprotic, or triprotic. This video also shows that polyprotic bases can accept more than one proton. Monoprotic acids have one ionizable hydrogen atom per molecule. Examples include HCl, HNO3, and HCN. Their reactions with water form hydronium ions and the matching anion. Acetic acid, CH3CO2H, is also monoprotic because only the hydrogen in the carboxyl group...

acid strength and molecular structure

Acid strength depends on bonding, electronegativity, and oxidation number. These factors help explain why some hydrogen compounds act as strong acids, while others behave as weak acids or bases. For binary acids, which are hydrogen compounds with one other nonmetal, acidity increases as the H-A bond gets weaker down a group. That is why the order for group 17 is HF &lt; HCl &lt; HBr &lt; HI, and for group 16 it is H2O &lt; H2S &lt; H2Se &lt; H2Te. Across a period, acid strength increases as...

lewis acids and bases

Electron-Pair Reactions in Acid-Base Chemistry

Electron-pair reactions explain Lewis acid-base chemistry. In 1923, G. N. Lewis described acids and bases by how they accept or donate a pair of electrons. When that electron pair forms a coordinate covalent bond, one atom supplies both bonding electrons. This bond is also called a dative bond. A simple example is the reaction of water with a hydrogen ion to make a hydronium ion. Ammonia can also combine with a hydrogen ion to form an ammonium ion. In both cases, the reaction creates a Lewis...

key terms and concepts

Learn how bond strength, electronegativity, oxidation number, and resonance help explain acid strength in binary acids, oxyacids, and carboxylic acids.

How Bonding Affects Acid Strength | JoVE K12

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How Bonding Affects Acid Strength

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