Name: resonance forms in lewis structures
Uploaded: 2020-09-03T13:38:28.000Z
Duration: 2 min 52 s
Channel: JoVE

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9-12

Chemistry

Matter and its Interactions

PS.Chm.3.1

Resonance

대부분의 분자와 이온은 고유한 루이스 구조를 사용하여 표현할 수 있습니다. 하지만 어떤 화합물은 동일하게 유효한 여러 루이스 구조로 나타날 수 있습니다. 삼산화황의 루이스 구조를 생각해 봅시다.

각 산소와 중앙에 있는 유황 원자들 사이의 단일 결합은 산소 원자에 대한 옥텟을 만족시킵니다. 하지만 유황에 대한 풀 옥텟에 도달하기 위해서는 유황과 어느 하나의 산소 원자 사이에 추가적인 결합이 형성되어야 합니다. 세 개의 산소 중 어떤 것이든 유황과 이중 결합을 형성할 수 있기 때문에 세 개의 다른 루이스 구조를 얻을 수 있습니다.

이 다중 루이스 구조를 공명 구조라고 하는데 이 구조에서 골격 구조는 그대로이지만 전자는 다르게 분포됩니다. 세 가지 구조는 모두 분자에 대해서 유효하고 동등한 표현이지만 자연계에는 모두 존재하지 않습니다. 실제 구조는 공명 구조물 사이에서 변동하는 것이 아니라 3개의 루이스 구조의 혼합 또는 평균입니다.

이것은 결합 길이로 측정할 수 있습니다. 아황산염에서 유황-산소 단일 결합의 길이는 1.51 옹스트롬인 반면 삼산화황에서는 유황-산소 결합 길이가 1.42 옹스트롬입니다. 그러므로 혼성 분자에서 결합 길이는 단일 결합과 이중 결합 사이의 중간 값입니다.

혼성 분자에서 이중 결합이나 고립 전자쌍에 참여하는 전자는 종종 다중 결합이나 원자에 걸쳐서 골고루 분포되는데 이것은 전자가 특정 원자에 고정되어 있지 않다는 것을 의미합니다. 비편제화는 전자의 위치 에너지를 감소시켜 공명 안정화라고 불리는 안정화를 이룹니다. 공명 현상은 또한 벤젠과 같은 방향족 화합물에서도 관찰됩니다.

벤젠은 육각형의 탄소 고리로 각 탄소 원자에 하나의 수소가 결합되고 탄소 원자들 사이에 단일 결합과 이중 결합이 교대로 바뀝니다. 벤젠은 탄소-탄소 이중 결합의 위치에 기초하여 두 개의 공명 구조를 가질 수 있습니다. 이중 결합이 보통 단일 결합에 비해 짧다는 것을 떠올려 봅시다 그러나 벤젠의 모든 탄소-탄소 결합은 탄소-탄소 단일 결합과 이중 결합 사이의 중간인 값과 동일한 결합 길이를 가지고 있습니다.

따라서 벤젠은 공명 혼성으로서 존재하며 내부가 원 형태인 육각형으로 표현될 수 있습니다. 원은 벤젠이 두 공명 구조의 혼합 구조를 가지며 이중 결합은 어떤 두 개의 특정 탄소 원자로도 국부화될 수 없음을 나타냅니다.

공명

아질산염 음이온(NO_2^-)의 루이스 구조는 실제로 NO와 N=O 결합의 위치에 따라 구별되는 두 가지 다른 방식으로 그려질 수 있습니다.

<img alt="Figure1" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;" />

아질산염 이온이 실제로 단일 결합과 이중 결합을 포함하고 있다면 두 결합 길이는 다를 것으로 예상됩니다. 두 원자 사이의 이중 결합은 동일한 두 원자 사이의 단일 결합보다 짧고 강합니다. 그러나 실험에 따르면 NO_2^−의 두 N-O 결합은 모두 동일한 강도와 길이를 가지며 다른 모든 특성도 동일합니다. 질소가 옥텟을 갖고 두 결합이 동등한 NO_2^−에 대한 단일 루이스 구조를 작성하는 것은 불가능합니다.

대신, 공명 개념이 사용됩니다. 동일한 원자 배열을 가진 두 개 이상의 루이스 구조가 분자나 이온에 대해 작성될 수 있는 경우 전자의 실제 분포는 다양한 루이스 구조에 의해 표시된 분포의 평균입니다. NO_2^-의 각 질소-산소 결합에서 전자의 실제 분포는 이중 결합과 단일 결합의 평균입니다.

개별 루이스 구조를 공명 형태라고 합니다. 분자의 실제 전자 구조(공명 형태의 평균)를 개별 공명 형태의 공명 하이브리드라고 합니다. 루이스 구조 사이의 양방향 화살표는 이것이 공명 형태임을 나타냅니다.

<img alt="Figure2" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;" />

탄산염 음이온인 CO_3^2−는 공명의 두 번째 예를 제공합니다.

<img alt="Figure3" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;" />

하나의 산소 원자는 중심 원자의 옥텟을 완성하기 위해 탄소에 이중 결합을 가져야 합니다.

그러나 모든 산소 원자는 동일하며 이중 결합은 세 원자 중 어느 하나에서 형성될 수 있습니다. 이는 탄산 이온의 세 가지 공명 형태를 발생시킵니다.

세 개의 동일한 공명 구조를 쓸 수 있으므로 탄산 이온의 실제 전자 배열은 세 구조의 평균으로 알려져 있습니다.

다시 한번 실험을 통해 세 개의 C-O 결합이 모두 정확히 동일하다는 것이 밝혀졌습니다.

<ol style="list-style-type: disc;">
</ol>

공명 하이브리드로 설명되는 분자는 공명 형태로 설명되는 전자 구조를 결코 보유하지 않는다는 점을 항상 기억하세요. 공명 형태 간에 변동되지 않습니다. 오히려 실제 전자 구조는 항상 모든 공명 형태로 나타나는 평균입니다.

공명 이론의 선구자 중 한 명인 조지 웰런드는 공명 형태와 공명 혼성체 사이의 관계를 설명하기 위해 역사적 비유를 사용했습니다. 코뿔소를 한 번도 본 적이 없는 한 중세 여행자는 코뿔소를 용과 유니콘의 잡종으로 묘사했는데, 그 이유는 코뿔소가 용과 유니콘과 공통점이 많았기 때문입니다. 코뿔소가 때로는 용도 아니고 때로는 유니콘도 아닌 것처럼, 공명 잡종도 주어진 시간에 공명 형태를 띠지 않습니다.

코뿔소처럼 그것은 실험적 증거가 존재하는 것으로 밝혀진 실제 존재입니다. 공명형태와 공통점이 있지만, 공명형태 자체가 편리하고 상상적인 이미지(유니콘이나 용처럼)입니다.

이 문서는 다음 링크에서 발췌되었습니다.

이 문서는 에서 발췌되었습니다 <a href="https://openstax.org/books/chemistry-2e/pages/7-4-formal-charges-and-resonance">Openstax, Chemistry 2e, Section 7.4: Formal Charges and Resonance.</a>

아질산염 음이온 (NO2-)의 루이스 구조는 실제로 N-O 및 N = O의 위치로 구별되는 두 가지 다른 방식으로 그려질 수 있습니다.

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resonance forms in lewis structures

Resonance forms in Lewis structures help explain molecules and ions that cannot be shown correctly with just one drawing. In nitrite ion, NO2−, the Lewis structure can be drawn in two ways. The N-O and N=O bonds switch positions in the two drawings, but the atoms stay in the same arrangement.

If nitrite really had one single bond and one double bond, the two bond lengths should be different. A double bond is shorter and stronger than a single bond between the same atoms. Experiments show that both N-O bonds in NO2− have the same length, strength, and other properties. That means the real structure is not one Lewis form alone.

Resonance is the idea used when two or more Lewis structures with the same atom arrangement can be written for one species. The actual electron distribution is an average of the electrons shown in the different forms. In NO2−, each N-O bond has an average of a single bond and a double bond. The separate Lewis structures are called resonance forms, and the real structure is called a resonance hybrid.

A double-headed arrow is written between resonance forms to show this relationship. Carbonate ion, CO3 2−, is another clear example. One oxygen must form a double bond to carbon to complete the carbon octet, but any of the three oxygen atoms can make that bond. This gives three resonance forms, and experiments show that all three C-O bonds are exactly the same.

A resonance hybrid never has the electronic structure of just one resonance form. It does not switch back and forth between forms. Instead, it always exists as the average of all the resonance forms. George Wheland used a historical comparison to explain this idea. A medieval traveler who had never seen a rhinoceros described it as a hybrid of a dragon and a unicorn, but a rhino is neither one at different times. In the same way, resonance forms are useful imaginary pictures, while the resonance hybrid is the real entity shown by evidence.

Resonance Forms in Lewis Structures

types of chemical bonds

Chemical Bonding and Bond Properties

Chemical bonding explains how atoms and ions join to form molecules and compounds. American chemist Gilbert N. Lewis pioneered chemical bonding theory with the Lewis model. This model helps explain why bonds form, why some are stronger than others, and why compounds have fixed formulas like H2O instead of H4O. Ionic bonding involves ions, which are atoms or molecules with an electrical charge. A cation is a positive ion formed when a neutral atom loses one or more electrons from its valence...

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Ionic Compounds and Crystal Lattices

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covalent bonding and lewis structures

Shared Electrons in Covalent Molecules

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resonance

Resonance forms in Lewis structures help explain molecules and ions that cannot be shown correctly with just one drawing. In nitrite ion, NO2−, the Lewis structure can be drawn in two ways. The N-O and N=O bonds switch positions in the two drawings, but the atoms stay in the same arrangement. If nitrite really had one single bond and one double bond, the two bond lengths should be different. A double bond is shorter and stronger than a single bond between the same atoms. Experiments show that...

formal charges

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Lewis structures can sometimes show more than one reasonable arrangement for a molecule or polyatomic ion. Formal charge helps chemists choose the best Lewis structure when that happens. It is a useful way to compare possible structures in chemistry. Formal charge is the hypothetical charge an atom would have if bonding electrons were shared evenly between the atoms. It can also be found by starting with the valence electrons of the neutral atom, subtracting the nonbonding electrons, and then...

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Learn how resonance forms explain equal bond lengths in nitrite and carbonate ions, and how a resonance hybrid represents the real electron distribution.

Resonance Forms in Lewis Structures | JoVE K12

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The electron affinity (EA) is the energy change for adding an electron to a gaseous atom to form an anion (negative ion).



This process can be either ...

Construct an explanation to infer the atomic size, reactivity, electronegativity, and ionization energy of an element based on its position in the Periodic Table.

PS.Chm.2.2

Types of Chemical Bonds

Chemical bonding theories were pioneered by American chemist Gilbert&#xA0;N. Lewis. He developed a model called the Lewis model to explain the type and ...

Lewis Symbols and the Octet Rule

Chemical bonds are complex interactions between two or more atoms or ions, which reduce the potential energy of the molecule. Gilbert N. Lewis developed a ...

Ionic Bonding and Electron Transfer

Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence ...

The Born-Haber Cycle

Lattice Energy&#xA0;

An ionic compound is stable because of the electrostatic attraction between its positive and negative ions. The lattice energy of a ...

Trends in Lattice Energy: Ion Size and Charge

An ionic compound is stable because of the electrostatic attraction between its positive and negative ions. The lattice energy of a compound is a measure ...

Covalent Bonding and Lewis Structures

Compared to ionic bonds, which results from the transfer of electrons between metallic and nonmetallic atoms, covalent bonds result from the mutual ...

Electronegativity

Whether a bond is nonpolar or polar covalent is determined by a property of the bonding atoms called electronegativity.&#xA0;

Electronegativity values of ...

Bond Polarity, Dipole Moment, and Percent Ionic Character

Bond Polarity

The absolute value of the difference in electronegativity (&Delta;EN) of two bonded atoms provides a rough measure of the polarity to be ...

Lewis Structures of Molecular Compounds and Polyatomic Ions

To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:


	Determine the ...

The Lewis structure of a nitrite anion (NO2&minus;) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O ...

Formal Charges

In some cases, there are seemingly more than one valid Lewis structures for molecules and polyatomic ions. The concept of formal charges can be used to ...

Exceptions to the Octet Rule

Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:


	...

Bond Energies and Bond Lengths

Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, ...

Analyze and interpret data to explain the mechanisms and properties of the two main types of intramolecular (ionic and covalent) bonds.

molecular-comparison-of-gases-liquids-and-solids

Molecular Comparison of Gases, Liquids, and Solids

Particles in a solid are tightly packed together (fixed shape) and often arranged in a regular pattern; in a liquid, they are close together with no ...

Intermolecular vs Intramolecular Forces

Intermolecular forces (IMF) are electrostatic attractions arising from charge-charge interactions between molecules. The strength of the intermolecular ...

Intermolecular Forces

Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions ...

comparing-intermolecular-forces-melting-point-boiling-point

Comparing Intermolecular Forces: Melting Point, Boiling Point, and Miscibility

Intermolecular forces are attractive forces that exist between molecules. They dictate several bulk properties, such as melting points, boiling points, ...

surface-tension-capillary-action-and-viscosity

Surface Tension, Capillary Action, and Viscosity

Surface Tension
The various IMFs between identical molecules of a substance are examples of cohesive forces. The molecules within a liquid are surrounded ...

Construct an explanation to summarize the influences intermolecular forces have on the properties of chemical compounds.

PS.Chm.3.2

Analyze the structure of atoms and isotopes.

Resonance Forms in Lewis Structures

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