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

El ácido clorhídrico es un ácido fuerte, mientras que el ácido fluorhídrico es un ácido débil. Pero, qué determina su fuerza? La fuerza de los ácidos binarios, con solo dos elementos, está determinada por la energía y la polaridad del enlace.Un ácido con una energía de enlace más alta tiene un enlace más fuerte y, por lo tanto, será un ácido más débil. Al comparar los ácidos de un grupo, el enlace de un ácido débil, como el ácido fluorhídrico, éste es más difícil de romper por lo que es menos probable que el ácido done protones. Por el contrario, un ácido con menos energía en su enlace tiene un enlace más débil y, por lo tanto, será un ácido más fuerte.Por ejemplo, el enlace en un ácido fuerte, como el ácido clorhídrico, se rompe más fácilmente y dona protones más fácilmente que el ácido fluorhídrico. Un enlace, como el del ácido clorhídrico, es polar cuando un átomo es más electronegativo que el otro. Un compuesto puede actuar como ácido cuando el átomo unido al hidrógeno tiene una mayor electronegatividad que el hidrógeno.El átomo tendrá una carga negativa parcial, lo que permitirá que el hidrógeno tenga una carga positiva parcial para que pueda liberarse como un protón. Un ácido con una polaridad de enlace más alta tiene un enlace más débil y, por lo tanto, será un ácido más fuerte. Al comparar compuestos a lo largo de un período, el ácido clorhídrico es más fuerte que el sulfuro de hidrógeno, ya que el cloro es más electronegativo que el azufre y, por lo tanto, libera protones con mayor facilidad.Si el hidrógeno tiene una electronegatividad igual o mayor que el otro átomo, esa molécula no puede donar protones y, por tanto, no puede actuar como ácido. Los oxiácidos son ácidos donde un OH está unido a un tercer átomo que es más electronegativo que el hidrógeno. La fuerza de un oxiácido depende de la electronegatividad y del número de oxígenos unidos al tercer átomo.Cuanto mayor es la electronegatividad del átomo, más se polariza, debilitando el enlace entre el oxígeno y el hidrógeno. Si el átomo central está unido a átomos de oxígeno adicionales aumenta aún más la polaridad del enlace entre el oxígeno y el hidrógeno. Por ejemplo, el ácido perclórico con tres átomos de oxígeno adicionales es más fuerte que el ácido clórico con dos átomos de oxígeno adicionales.El ácido clórico, a su vez, es más fuerte que el ácido cloroso, que tiene solo un oxígeno adicional y que el ácido hipocloroso, sin átomos de oxígeno adicionales. Los ácidos carboxílicos son ácidos débiles que contienen un grupo carboxilo. El segundo átomo de oxígeno hace que el enlace oxígeno-hidrógeno sea más polar y, por lo tanto, permite que la molécula done un protón.El ácido acético y el ácido fórmico son ejemplos de ácidos carboxílicos.

fuerza y estructura molecular de los Ácidos

Ácidos y bases binarios
 En ausencia de cualquier efecto de nivelación, la fuerza ácida de los compuestos binarios de hidrógeno con no metales (A) aumenta a medida que la fuerza del enlace H-A disminuye en un grupo de la tabla periódica. Para el grupo 17, el orden de aumento de la acidez es HF < HCl < HBr &#60 HI. Asimismo, para el grupo 16, el orden de aumento de la fuerza ácida es H2O < H2S < H2Se < H2Te. A lo largo de una fila en la tabla periódica, la fuerza ácida de los compuestos binarios de hidrógeno aumenta con el aumento de la electronegatividad del átomo no metálico debido a la polaridad del enlace H-A. Así, el orden de aumento de la acidez (para la remoción de un protón) en la segunda fila es de CH4 < NH3 < H2O < HF; en la tercera fila, es SiH4 < PH3 < H2S < HCl.
 Ácidos y bases ternarios
 Los compuestos ternarios formados por hidrógeno, oxígeno y algún tercer elemento (“E&8221;) pueden estructurarse como se muestra en la imagen siguiente. En estos compuestos, el átomo central E está unido a uno o más átomos O, y al menos uno de los átomos O también está unido a un átomo H, correspondiente a la fórmula molecular general OmE(OH)n. Estos compuestos pueden ser ácidos, básicos o anfotéricos dependiendo de las propiedades del átomo E central. Ejemplos de tales compuestos incluyen ácido sulfúrico, O2S(OH)2, ácido sulfuroso, OS(OH)2, ácido nítrico, O2NOH, ácido perclórico, O3ClOH, hidróxido de aluminio, Al(OH)3, Hidróxido de calcio, Ca(OH)2 e hidróxido de potasio, KOH.
 <img alt="Eq1" src="/files/ftp_upload/11406/11406_Figure_1.svg" style="height: 90px;" />
 Si el átomo central, E, tiene una baja electronegatividad, su atracción por los electrones es baja. Existe una baja tendencia a que el átomo central forme un fuerte enlace covalente con el átomo de oxígeno, y el enlace a entre el elemento y el oxígeno se rompe más fácilmente que el enlace b entre el oxígeno y el hidrógeno. Por lo tanto, el enlace a es iónico, los iones hidróxido se liberan a la solución, y el material se comporta como una base—este es el caso con el Ca(OH)2 y KOH. La electronegatividad más baja es característica de los elementos más metálicos; por lo tanto, los elementos metálicos forman hidróxidos iónicos que son, por definición, compuestos básicos.
 Si, por otro lado, el átomo E tiene una electronegatividad relativamente alta, atrae fuertemente a los electrones que comparte con el átomo de oxígeno, haciendo un enlace covalente relativamente fuerte. El enlace oxígeno-hidrógeno, enlace b, se debilita por lo tanto porque los electrones se desplazan hacia E. El enlace b es polar y libera fácilmente iones hidrógeno a la solución, por lo que el material se comporta como un ácido. Las electronegatividades altas son características de los elementos no metálicos. Por lo tanto, los elementos no metálicos forman compuestos covalentes que contienen grupos ácidos −OH que se llaman oxácidos.
 El aumento del número de oxidación del átomo central E también aumenta la acidez de un oxácido porque esto aumenta la atracción de E por los electrones que comparte con el oxígeno y por lo tanto debilita el enlace O-H. El ácido sulfúrico, H2SO4 o O2S(OH)2 (con un número de oxidación del azufre de +6), es más ácido que el ácido sulfuroso, H2SO3, o que el OS(OH)2 (con un número de oxidación del azufre de +4). Del mismo modo, el ácido nítrico, HNO3 o el O2NOH (número de oxidación del N = +5), es más ácido que el ácido nitroso, HNO2 o que el ONOH (número de oxidación del N = +3). En cada uno de estos pares, el número de oxidación del átomo central es mayor para el ácido más fuerte.
 Ácidos carboxílicos
 Los ácidos carboxílicos contienen un grupo carboxilo. Los ácidos carboxílicos son ácidos débiles, lo que significa que no están ionizados al 100% en el agua.
 El ácido carboxílico actúa como un ácido débil porque, como en el caso de los oxácidos, el segundo oxígeno unido al átomo de carbono aumenta la polaridad del enlace O-H y lo hace más débil. Además, después de la pérdida del protón, el grupo carboxilo se convierte en el ión carboxilato, que exhibe resonancia. Las diferentes estructuras de resonancia estabilizan el ión carboxilato a medida que su carga negativa se deslocaliza sobre varios átomos.
 Este texto es adaptado de<a href="https://openstax.org/books/chemistry-2e/pages/14-3-relative-strengths-of-acids-and-bases"> Openstax, Química 2e, Sección 14.3: Fuerzas Relativas de Ácidos y Bases</a> y<a href="https://openstax.org/books/chemistry-2e/pages/20-3-aldehydes-ketones-carboxylic-acids-and-esters"> Openstax, Química 2e, Sección 20.3 Aldehídos, Cetonas, Ácidos carboxílicos, Y ésteres</a>.

Fuerza y Estructura Molecular de los Ácidos

Ácidos y bases binarias
En ausencia de cualquier efecto nivelador, la fuerza ácida de los compuestos binarios de hidrógeno con no metales (A) aumenta a medida que el H-A ...

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Ácidos y bases

KEY TERMS AND CONCEPTS

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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

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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...

determining the ph of salt solutions

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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