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

Kwas solny jest mocnym kwasem, podczas gdy kwas fluorowodorowy jest słabym kwasem. Ale co decyduje o ich sile?
Siła kwasów dwuskładnikowych, składających się tylko z dwóch pierwiastków, zależy od energii wiązania i polaryzacji wiązania.
Kwas o wyższej energii wiązania ma silniejsze wiązanie, a zatem będzie słabszym kwasem. Porównując kwasy w grupie, wiązanie w słabym kwasie, takim jak kwas fluorowodorowy, jest trudniejsze do zerwania, więc kwas jest mniej skłonny do oddawania protonów.
Natomiast kwas o niższej energii wiązania ma słabsze wiązanie, a zatem będzie silniejszym kwasem. Na przykład wiązanie w mocnym kwasie, takim jak kwas solny, łatwiej się zrywa i łatwiej oddaje protony niż kwas fluorowodorowy.
Wiązanie, takie jak w kwasie solnym, jest polarne, gdy jeden atom jest bardziej elektroujemny niż drugi atom.
Związek może działać jak kwas, gdy atom przyłączony do wodoru ma wyższą elektroujemność niż wodór. Atom będzie miał częściowy ładunek ujemny, dzięki czemu wodór będzie miał częściowy ładunek dodatni, dzięki czemu może zostać uwolniony jako proton.
Kwas o wyższej polarności wiązania ma słabsze wiązanie, a zatem będzie silniejszym kwasem.
Porównując związki w okresie, kwas solny jest silniejszy niż siarkowodór, ponieważ chlor jest bardziej elektroujemny niż siarka, a zatem łatwiej uwalnia protony.
Jeśli wodór ma równą lub większą elektroujemność niż drugi atom, cząsteczka ta nie może oddawać protonów, a zatem nie może działać jako kwas.
Kwasy tlenowe to kwasy, w których OH jest przyłączony do trzeciego atomu, który jest bardziej elektroujemny niż wodór. Siła kwasu tlenowego zależy od elektroujemności i liczby tlenu przyłączonego do trzeciego atomu.
Im wyższa elektroujemność atomu, tym bardziej polaryzuje się, osłabiając wiązanie między tlenem a wodorem.
Jeśli centralny atom jest przyłączony do dodatkowych atomów tlenu, dodatkowo zwiększa to polaryzację wiązania między tlenem a wodorem.
Na przykład kwas nadchlorowy z trzema dodatkowymi atomami tlenu jest silniejszy niż kwas chlorowy z dwoma dodatkowymi atomami tlenu. Kwas chlorowy z kolei jest silniejszy od kwasu chlorawego, który ma tylko jeden dodatkowy tlen i kwas podchlorawy, bez dodatkowych atomów tlenu.
Kwasy karboksylowe to słabe kwasy, które zawierają grupę karboksylową. Drugi atom tlenu sprawia, że wiązanie tlen-wodór jest bardziej polarne, a tym samym pozwala cząsteczce oddać proton. Kwas octowy i kwas mrówkowy są przykładami kwasów karboksylowych.

siła kwasu i struktura molekularna

Binarne kwasy i zasady

W przypadku braku jakiegokolwiek efektu wyrównywania, siła kwasowa binarnych związków wodoru z niemetalami (A) wzrasta wraz ze spadkiem siły wiązania H-A w dół grupy w układzie okresowym. Dla grupy 17 rząd rosnącej kwasowości to HF < HCl < HBr < HI. Podobnie dla grupy 16, rząd rosnącej mocy kwasu jest następujący: H2O < H2S < H2Se < H2Te. W wierszu układu okresowego siła kwasu binarnych związków wodoru wzrasta wraz ze wzrostem elektroujemności atomu niemetalu, ponieważ zwiększa się polarność wiązania H-A. Zatem rząd rosnącej kwasowości (w celu usunięcia jednego protonu) w drugim rzędzie jest następujący: CH4 < NH3 < H2O < HF; w trzecim rzędzie jest to SiH4 < PH3 < H2S < HCl.

Trójskładnikowe kwasy i zasady

Związki trójskładnikowe składające się z wodoru, tlenu i pewnego trzeciego pierwiastka („E”) mogą mieć strukturę jak pokazano na poniższym obrazku. W tych związkach centralny atom E jest związany z jednym lub większą liczbą atomów O i co najmniej jeden z atomów O jest również związany z atomem H, co odpowiada ogólnemu wzorowi cząsteczkowemu OmE(OH)n. Związki te mogą być kwasowe, zasadowe lub amfoteryczne, w zależności od właściwości centralnego atomu E. Przykłady takich związków obejmują kwas siarkowy, O2S(OH)2, kwas siarkawy, OS(OH)2, kwas azotowy, O2NOH, kwas nadchlorowy, O3ClOH, wodorotlenek glinu, Al(OH)3, wodorotlenek wapnia, Ca(OH)2 i wodorotlenek potasu, KOH.

<img alt="Eq1" src="/files/ftp_upload/11406/11406_Figure_1.svg" style="height: 90px;" />

Jeśli atom centralny E ma niską elektroujemność, jego przyciąganie elektronów jest niskie. Istnieje niewielka tendencja, aby atom centralny tworzył silne wiązanie kowalencyjne z atomem tlenu, a wiązanie a między pierwiastkiem a tlenem jest łatwiej zerwane niż wiązanie b między tlenem i wodorem. Zatem wiązanie a jest jonowe, do roztworu uwalniają się jony wodorotlenkowe, a materiał zachowuje się jak zasada – tak jest w przypadku Ca(OH)2 i KOH. Niższa elektroujemność jest charakterystyczna dla pierwiastków bardziej metalicznych; stąd pierwiastki metaliczne tworzą wodorotlenki jonowe, które z definicji są związkami zasadowymi.

Jeżeli natomiast atom E ma stosunkowo wysoką elektroujemność, to silnie przyciąga elektrony, które dzieli z atomem tlenu, tworząc stosunkowo silne wiązanie kowalencyjne. Wiązanie tlen-wodór, wiązanie b, jest w ten sposób osłabiane, ponieważ elektrony są przemieszczane w kierunku E. Wiązanie b jest polarne i łatwo uwalnia jony wodorowe do roztworu, więc materiał zachowuje się jak kwas. Wysokie elektroujemności są charakterystyczne dla pierwiastków bardziej niemetalicznych. Zatem pierwiastki niemetaliczne tworzą związki kowalencyjne zawierające kwasowe grupy -OH, które nazywane są kwasami tlenowymi.

Zwiększanie stopnia utlenienia centralnego atomu E zwiększa również kwasowość kwasu tlenowego, ponieważ zwiększa to przyciąganie E dla elektronów wspólnych z tlenem, a tym samym osłabia wiązanie OH. Kwas siarkowy, H2SO4 lub O2S(OH)2 (o stopniu utlenienia siarki +6), jest bardziej kwaśny niż kwas siarkawy, H2SO3 lub OS(OH)2 (o stopniu utlenienia siarki +4). Podobnie kwas azotowy, HNO3 lub O2NOH (stopień utlenienia N = +5), jest bardziej kwaśny niż kwas azotawy, HNO2 lub ONOH (stopień utlenienia N = +3). W każdej z tych par stopień utlenienia atomu centralnego jest większy dla silniejszego kwasu.

Kwasy karboksylowe

Kwasy karboksylowe zawierają grupę karboksylową. Kwasy karboksylowe są słabymi kwasami, co oznacza, że nie są w 100% zjonizowane w wodzie.

Kwas karboksylowy działa jak słaby kwas, ponieważ podobnie jak w przypadku kwasów tlenowych, drugi tlen przyłączony do atomu węgla zwiększa polarność wiązania O-H i osłabia je. Ponadto po utracie protonu grupa karboksylowa ulega konwersji do jonu karboksylanowego, który wykazuje rezonans. Różne struktury rezonansowe stabilizują jon karboksylanowy, ponieważ jego ładunek ujemny jest przenoszony na kilka atomów.

Siła kwasu i struktura molekularna

Binarne kwasy i zasady
W przypadku braku efektu wyrównującego kwasowość dwuskładnikowych związków wodoru z niemetalami (A) wzrasta wraz z H-A ...

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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

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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 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 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...

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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...

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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

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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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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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determining the ph of salt solutions

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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...

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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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