Name: resonance forms in lewis structures
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Chemistry

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PS.Chm.3.1

Resonance

Çoğu molekül ve iyon, benzersiz Lewis yapıları kullanılarak temsil edilebilir. Bununla birlikte, belirli bileşikler birden çok, eşit derecede geçerli Lewis yapıları ile gösterilebilir. Kükürt trioksit için Lewis yapısını düşünün.Her oksijen ve merkezi sülfür atomları arasındaki tek bağlar, oksijen atomları için sekizliyi karşılar. Bununla birlikte, kükürt için tam bir oktete ulaşmak için, kükürt ile oksijen atomlarından biri arasında ek bir bağ oluşması gerekir. Üç oksijenden herhangi biri kükürt ile çift bağ oluşturabileceğinden, üç farklı Lewis yapısı çizilebilir.Bu çoklu Lewis yapıları, iskelet yapılarının aynı kaldığı ancak elektronların farklı şekilde dağıldığı rezonans yapıları olarak adlandırılır. Üç yapı da molekülün geçerli ve eşdeğer temsilleridir, ancak hepsi doğada mevcut değildir. Gerçek yapı, rezonans yapıları arasında salınım yapmaz, ancak bağ uzunluklarıyla ölçülebilen üç Lewis yapısının bir melezi veya ortalamasıdır.Sülfitte, bir kükürt-oksijen tek bağının uzunluğu 1, 51 angstrom iken, kükürt trioksitte kükürt-oksijen bağ uzunluğu 1, 42 angstromdur. Dolayısıyla, hibrit molekülde bağ uzunluğu, tek ve çift bağlar arasında bir ara maddedir. Hibrit moleküllerde, çift bağlara veya yalnız çiftlere katılan elektronlar, genellikle birden fazla bağ veya atom üzerinde yer değiştirir, yani belirli bir atom üzerinde durağan değillerdir.Delokalizasyon, elektronların potansiyel enerjisini düşürerek rezonans stabilizasyonu adı verilen stabilizasyona neden olur. Benzen gibi aromatik bileşiklerde de rezonans durumu gözlemlenir. Benzen, karbon atomlarının her birine bir hidrojen bağlı ve karbon atomları arasında değişen tek ve çift bağlara sahip altıgen bir karbon halkasıdır.Karbon-karbon çift bağlarının konumuna bağlı olarak, benzen iki rezonans yapısına sahip olabilir. İkili bağların genellikle tekli bağlardan daha kısa olduğunu hatırlayın. Bununla birlikte, benzendeki tüm karbon-karbon bağları, karbon-karbon tek ve çift uzunluklarının arasında ve eşit uzunluklara sahiptir.Benzen, bu nedenle, bir rezonans melezi olarak bulunur ve ortasında bir halka bulunun altıgen şeklinde gösterilebilir. Ortadaki halka yapısı benzenin iki adet rezonans yapısının karışımı olduğunu ve herhangi iki spesifik karbon atomuna lokalize edilemeyeceğini gösterir.

rezonans

Bir nitrit anyonunun (NO2−) Lewis yapısı aslında N-O ve N=O bağlarının konumları ile ayırt edilen iki farklı şekilde çizilebilir. 
 
 <img alt="Figure1" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;" />
 
 Nitrit iyonları gerçekten bir tek ve bir çift bağ içeriyorsa, iki bağ uzunluğunun farklı olması beklenir. İki atom arasındaki çift bağ, aynı iki atom arasındaki tek bağdan daha kısadır (ve daha güçlüdür). Ancak deneyler NO2−'daki her iki N–O bağının aynı güç ve uzunluğa sahip olduğunu ve diğer tüm özelliklerde aynı olduğunu göstermektedir. Nitrojenin oktet olduğu ve her iki bağın da eşdeğer olduğu NO2− için tek bir Lewis yapısı yazmak mümkün değildir.
 
 Bunun yerine, rezonans kavramı kullanılır: eğer aynı atom düzenlemesine sahip iki veya daha fazla Lewis yapısı bir molekül veya iyon için yazılabilirse, elektronların gerçek dağılımı, çeşitli Lewis yapıları tarafından gösterilenlerin ortalamasıdır. NO2− 'deki nitrojen-oksijen bağlarının her birindeki elektronların gerçek dağılımı, bir çift bağ ve bir tek bağın ortalamasıdır. 
 
 Bireysel Lewis yapılarına rezonans formları denir. Molekülün gerçek elektronik yapısı (rezonans formlarının ortalaması), bireysel rezonans formlarının bir rezonans melezi olarak adlandırılır. Lewis yapıları arasındaki çift başlı ok, bunların rezonans formları olduğunu gösterir.
 
 <img alt="Figure2" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;" />
 
 Karbonat anyonu, CO3&minus2;, ikinci bir rezonans örneği sağlar. 
 
 <img alt="Figure3" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;" />
 
 <ul>
 <li>Bir oksijen atomunun, merkezi atomdaki oktete tamamlamak için bir karbona çift bağa sahip olması gerekir. </li>
 <li>Bununla birlikte, tüm oksijen atomları eşdeğerdir ve çift bağ, üç atomun herhangi birinden oluşabilir. Bu, karbonat iyonunun üç rezonans formuna yol açar. </li>
 <li>Üç özdeş rezonans yapısı yazılabildiğinden, karbonat iyonundaki elektronların gerçek düzeninin, üç yapının ortalaması olduğu bilinmektedir. </li>
 <li>Yine deneyler, üç C–O bağının da tamamen aynı olduğunu gösteriyor.</li>
 </ul>
 
 Rezonans hibridi olarak tanımlanan bir molekülün, her iki rezonans formu tarafından tanımlanan elektronik bir yapıya asla sahip olmadığını her zaman hatırlayın. Rezonans biçimleri arasında dalgalanma göstermez; daha ziyade, gerçek elektronik yapı her zaman tüm rezonans formları tarafından gösterilenin ortalamasıdır. 
 
 Rezonans teorisinin öncülerinden George Wheland, rezonans formları ve rezonans hibridleri arasındaki ilişkiyi tanımlamak için tarihsel bir analoji kullandı. Daha önce hiç gergedan görmemiş olan bir ortaçağ gezgini, onu bir ejderha ve tek boynuzlu atın hibridi olarak tanımlardı, çünkü her ikisiyle ortak birçok özelliği vardır. Tıpkı bir gergedanın ne bazen bir ejderha, ne de diğer zamanlarda tek boynuzlu at olmadığı gibi, bir rezonans hibridi de herhangi bir zamanda rezonans formlarından biri değildir.
 
 Bir gergedan gibi, deneysel kanıtların var olduğunu gösterdiği gerçek bir varlıktır. Rezonans formlarıyla ortak bazı özellikleri vardır, ancak rezonans formlarının kendileri uygun, hayali imgelerdir (tek boynuzlu at ve ejderha gibi).
 
 Bu metin bu kaynaktan uyarlanmıştır: <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>

Rezonans

Bir nitrit anyonunun (NO2−) Lewis yapısı aslında N-O ve N=O'nun konumları ile ayırt edilen iki farklı şekilde çizilebilir.

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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

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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...

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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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Resonance Forms in Lewis Structures

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