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

Matter and its Interactions

PS.Chm.3.1

Resonance

La maggior parte delle molecole e degli ioni possono essere rappresentati utilizzando strutture di Lewis uniche. Tuttavia, alcuni composti possono essere mostrati da più strutture di Lewis ugualmente valide. Considerate la struttura di Lewis per il triossido di zolfo.

I singoli legami tra ogni ossigeno e gli atomi di zolfo centrali soddisfano l'ottetto per gli atomi di ossigeno. Tuttavia, per raggiungere un ottetto completo per lo zolfo, è necessario formare un legame aggiuntivo tra lo zolfo e uno degli atomi di ossigeno. Poiché uno qualsiasi dei tre ossigeni può formare un doppio legame con lo zolfo, è possibile disegnare tre diverse strutture di Lewis.

Queste strutture di Lewis multiple sono dette strutture di risonanza, dove le strutture scheletriche rimangono le stesse, ma gli elettroni sono distribuiti in modo diverso. Tutte e tre le strutture sono rappresentazioni valide ed equivalenti della molecola, ma tutte sono inesistenti in natura. La struttura effettiva non oscilla fra le strutture di risonanza, ma è un ibrido, o una media, delle tre strutture di Lewis, che può essere misurata in lunghezze di legame.

Nel solfito, la lunghezza di un legame singolo zolfo-ossigeno è 1, 51 angstrom, mentre nel triossido di zolfo, la lunghezza del legame zolfo-ossigeno è 1, 42 angstrom. Pertanto, nella molecola ibrida, la lunghezza del legame è un intermedio fra i legami singoli e doppi. Nelle molecole ibride, gli elettroni che partecipano ai doppi legami o a coppie solitarie sono spesso delocalizzati su più legami o atomi, il che significa che non sono stazionari su un particolare atomo.

La delocalizzazione riduce l'energia potenziale degli elettroni con conseguente stabilizzazione, detta stabilizzazione della risonanza. La risonanza si osserva anche per i composti aromatici come il benzene. Il benzene è un anello di carbonio esagonale con un idrogeno legato a ciascuno degli atomi di carbonio e legami singoli e doppi alternati fra gli atomi di carbonio.

In base alla posizione dei doppi legami carbonio-carbonio, il benzene può avere due strutture di risonanza. Ricordate che i doppi legami sono generalmente più brevi dei singoli legami. Tuttavia, tutti i legami carbonio-carbonio nel benzene hanno lunghezze di legame uguali, che sono intermedie fra i legami carbonio-carbonio singoli e doppi.

Il benzene, quindi, esiste come ibrido di risonanza e può essere rappresentato come un esagono con un cerchio all'interno. Il cerchio indica che il benzene è una miscela di due strutture di risonanza e i doppi legami non possono essere localizzati in due specifici atomi di carbonio.

risonanza

La struttura di Lewis di un anione nitrito (NO_2^−) può in realtà essere disegnata in due modi diversi, distinti dalla posizione dei legami N-O e N=O.

<img alt="Figure1" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;" />

Se gli ioni nitrito contengono effettivamente un legame singolo e uno doppio, ci si aspetta che le lunghezze dei due legami siano diverse. Un doppio legame tra due atomi è più corto (e più forte) di un legame singolo tra gli stessi due atomi. Tuttavia, gli esperimenti mostrano che entrambi i legami N–O in NO_2^− hanno la stessa forza e lunghezza e sono identici in tutte le altre proprietà. Non è possibile scrivere un’unica struttura di Lewis per NO_2^− in cui l’azoto ha un ottetto ed entrambi i legami sono equivalenti.

Viene invece utilizzato il concetto di risonanza: se per una molecola o uno ione si possono scrivere due o più strutture di Lewis con la stessa disposizione degli atomi, la distribuzione effettiva degli elettroni è una media di quella mostrata dalle varie strutture di Lewis. La distribuzione effettiva degli elettroni in ciascuno dei legami azoto-ossigeno in NO_2^− è la media di un doppio legame e di un legame singolo.

Le singole strutture di Lewis sono chiamate forme di risonanza. La struttura elettronica effettiva della molecola (la media delle forme di risonanza) è chiamata ibrido di risonanza delle singole forme di risonanza. Una freccia a doppia punta tra le strutture di Lewis indica che si tratta di forme di risonanza.

<img alt="Figure2" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;" />

L'anione carbonato, CO_3^2^−, fornisce un secondo esempio di risonanza.

<img alt="Figure3" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;" />

<ol style="list-style-type: disc;">
	<li>Un atomo di ossigeno deve avere un doppio legame con un carbonio per completare l'ottetto sull'atomo centrale.</li>
	<li>Tutti gli atomi di ossigeno, tuttavia, sono equivalenti e il doppio legame potrebbe formarsi da uno qualsiasi dei tre atomi. Ciò dà origine a tre forme di risonanza dello ione carbonato.</li>
	<li>Visto che è possibile scrivere tre strutture di risonanza identiche, è noto che la disposizione effettiva degli elettroni nello ione carbonato è la media delle tre strutture.</li>
	<li>Ancora una volta, gli esperimenti mostrano che tutti e tre i legami C–O sono esattamente gli stessi.</li>
</ol>

Ricorda sempre che una molecola descritta come ibrida di risonanza non possiede mai una struttura elettronica descritta da nessuna delle due forme di risonanza. Non fluttua tra le forme di risonanza; piuttosto, la struttura elettronica effettiva è sempre la media di quella mostrata da tutte le forme di risonanza.

George Wheland, uno dei pionieri della teoria della risonanza, usò un'analogia storica per descrivere la relazione tra forme di risonanza e ibridi di risonanza. Un viaggiatore medievale, non avendo mai visto prima un rinoceronte, lo descrisse come un ibrido tra un drago e un unicorno perché aveva molte proprietà in comune con entrambi. Proprio come un rinoceronte non è né un drago né un unicorno, un ibrido di risonanza non è nessuna delle sue forme di risonanza in un dato momento.

Come un rinoceronte, è un'entità reale di cui le prove sperimentali hanno dimostrato l'esistenza. Ha alcune caratteristiche in comune con le sue forme di risonanza, ma le forme di risonanza stesse sono immagini convenienti e immaginarie (come l'unicorno e il drago).

Questo testo è adattato da <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>

Risonanza

La struttura di Lewis di un anione nitrito (NO2−) può in realtà essere disegnata in due modi diversi, distinti dalle posizioni di N-O e N=O ...

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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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