Name: how bonding affects acid strength
Uploaded: 2020-09-24T15:06:51.000Z
Duration: 3 min 5 s
Channel: JoVE

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Chemistry

Matter and its Interactions

PS.Chm.6.3

Acid Strength and Molecular Structure

塩酸は強酸ですが、フッ化水素酸は弱酸です。しかし、何が彼らの強さを決定するのでしょうか?
2つの元素のみを含む二元酸の強度は、結合エネルギーと結合極性によって決まります。
結合エネルギーが高い酸は結合が強いため、酸が弱くなります。グループ内の酸を比較すると、フッ化水素酸のような弱酸の結合は壊れにくいため、酸がプロトンを提供する可能性が低くなります。
対照的に、結合エネルギーが低い酸は結合が弱いため、より強い酸になります。たとえば、塩酸のような強酸の結合は、フッ化水素酸よりも簡単に切断され、プロトンを提供しやすくなります。
塩酸のような結合は、一方の原子がもう一方の原子よりも電気陰性度が高い場合、極性になります。
水素に結合した原子が水素よりも高い電気陰性度を持つ場合、化合物は酸として作用することができます。原子は部分的な負電荷を持つため、水素は部分的な正電荷を持つことができるため、陽子として放出できます。
結合極性が高い酸は結合が弱いため、より強い酸になります。
期間をまたいで化合物を比較すると、塩素は硫黄よりも電気陰性度が高く、したがって陽子を放出しやすいため、塩酸は硫化水素よりも強力です。
水素が他の原子と同等またはそれ以上の電気陰性度を持っている場合、その分子はプロトンを供与できないため、酸として作用することはできません。
オキシ酸は、水素よりも電気陰性度の高い第3の原子にOHが結合している酸です。オキシ酸の強度は、電気陰性度と3番目の原子に結合している酸素の数に依存します。
原子の電気陰性度が高いほど、原子は分極し、酸素と水素の間の結合を弱めます。
中心原子が追加の酸素原子に結合している場合、酸素と水素との間の結合の極性がさらに増加します。
たとえば、酸素原子が3つ追加された過塩素酸は、酸素原子が2つ追加された塩素酸よりも強力です。一方、塩素酸は、酸素が1つしかなく、次亜塩素酸が1つしかなく、酸素原子が追加されていない亜塩素酸よりも強力です。
カルボン酸は、カルボキシル基を含む弱酸です。2番目の酸素原子は、酸素-水素結合をより極性にし、それによって分子がプロトンを供与することを可能にします。酢酸とギ酸はカルボン酸の例です。

酸性強度と分子構造

二元系の酸と塩基
 平衡効果がない場合、水素と非金属（A）からなる二元化合物の酸強度は、H-A結合の強さが周期表の1つ下のグループになるほど大きくなります。17族の場合、酸性度の高い順に、HF < HCl < HBr < HI となります。同様に、16族については、酸の強さが大きくなる順に、H2O < H2S < H2Se < H2Teとなります。周期表のある周期で見ると、二元系水素化合物の酸強度は、非金属原子の電気陰性度が高くなると、H-A結合の極性が高くなるために増加します。したがって、第2周期の酸度（プロトンを1個除去した場合）の増加順は、CH4 < NH3 < H2O < HF; 3周期目は、SiH4 < PH3 < H2S < HClとなります。
 三元系の酸と塩基
 水素、酸素、そして三種類目の元素（ “E”）からなる三元化合物は、下図のような構造をとることがあります。これらの化合物では、中心のE原子が1つ以上のO原子と結合し、さらにO原子の少なくとも1つがH原子と結合しており、一般的な分子式OmE(OH)nに対応しています。これらの化合物は、中心のE原子の性質によって、酸性、塩基性、両性のいずれかになります。このような化合物の例としては、硫酸（O2S(OH)2）、亜硫酸（OS(OH)2）、硝酸（O2NOH）、過塩素酸 （O3ClOH）、水酸化アルミニウム（Al(OH)3）、水酸化カルシウム（Ca(OH)2）、水酸化カリウム（KOH）などがあります。
 
 <img alt="Eq1" src="/files/ftp_upload/11406/11406_Figure_1.svg" style="height: 90px;" />
 中心となる原子Eの電気陰性度が低い場合、電子に対する引力が小さくなります。中心原子が酸素原子と強い共有結合を形成する傾向はほとんどなく、元素と酸素の間の結合aは、酸素と水素の間の結合bよりも容易に切断されます。したがって、結合aはイオン性であり、水酸化物イオンが溶液中に放出され、物質は塩基として振舞います。金属元素は電気陰性度が低い特徴があるため、金属元素はイオン性の水酸化物を形成し、定義上は塩基性化合物となります。
 一方、原子Eが比較的高い電気陰性度を持つ場合、酸素原子と共有する電子を強く引き寄せ、比較的強い共有結合を作ます。酸素-水素結合である結合bは、電子がEの方に移動して弱くなります。結合bは極性を持ち、水素イオンを溶液中に放出しやすいため、物質は酸として振舞います。多くの非金属元素は、高い電気陰性度を有しています。そのため、非金属元素は酸性の −OH基を持つ共有結合を形成し、これをオキシ酸と呼びます。
 中心原子Eの酸化数を増やすと、酸素と共有する電子に対するEの引力が大きくなり、O-H結合が弱くなるため、オキシ酸の酸性度も高くなります。硫酸（H2SO4、またはO2S(OH)2（硫黄の酸化数は+6））は、亜硫酸（H2SO3、またはOS(OH)2（硫黄の酸化数は+4））よりも酸性度が高いです。同様に、硝酸（HNO3、またはO2NOH（N酸化数＝＋5））は、亜硝酸（HNO2、またはONOH（N酸化数＝＋3））よりも酸性度が高いです。これらのペアでは、いずれも中心原子の酸化数が大きいほど強い酸となります。
 カルボン酸類
 カルボン酸には、カルボキシル基があります。カルボン酸は弱酸性であり、水中では一部のみが電離します。
 カルボン酸が弱酸として作用するのは、オキシ酸の場合と同様に、炭素原子に結合した第2の酸素がO-H結合の極性を高めて弱くするためです。さらに、プロトンが失われた後のカルボキシル基はカルボン酸イオンに変化し、共鳴構造をとります。この共鳴構造によって、カルボン酸イオンの負電荷が複数の原子に分散されることで、イオンとして安定化します。
 上記の文章は以下から引用しました。<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> and <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>.

二元酸および二元酸および塩基
レベリング効果がない場合、水素と非金属(A)の二元化合物の酸強度は、H-A...

Education

JoVE Core

化学

Acids and Bases

酸と塩基

KEY TERMS AND CONCEPTS

主要用語と概念

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

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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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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...

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Strong Acids, Strong Bases, and pH

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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...

weak base solutions

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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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...

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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

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acid/base strengths and dissociation constants

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Stepwise Ionization of Polyprotic Acids

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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...

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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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JoVE Core 化学は、簡潔で理解しやすいアニメーションビデオレッスンを使用して、一般的な化学の概念を生き生きとしたものにします。さらに、活動する科学者のビデオでは、現在世界中の実験室で行われている古典的そして独創的な研究・実験をお見せします。

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HS-PS1-11.

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How Bonding Affects Acid Strength

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