Name: resonance forms in lewis structures
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Resonance

La plupart des molécules et des ions peuvent être représentés en utilisant des structures uniques de Lewis. Cependant, certains composés peuvent être représentés par de multiples structures de Lewis également valides. Considérons la structure de Lewis pour le trioxyde de soufre.Les liaisons simples entre chaque oxygène et les atomes de soufre centraux satisfont l'octet pour les atomes d'oxygène. Cependant, pour atteindre un octet complet pour le soufre, une liaison supplémentaire doit être formée entre le soufre et l'un des atomes d'oxygène. Étant donné que l'un des trois oxygènes peut former la double liaison avec le soufre, trois structures de Lewis différentes peuvent être dessinées.Ces multiples Lewis structures sont appelées structures de résonance, où les structures squelettiques restent les mêmes, mais les électrons sont distribués différemment. Les trois structures sont des représentations valides et équivalentes de la molécule, mais toutes sont inexistantes dans la nature. La structure réelle n'oscille pas entre les structures de résonance, mais est un hybride ou une moyenne des trois structures de Lewis, qui peut être mesurée en longueurs de liaison.Dans le sulfite, la longueur d'une liaison simple soufre-oxygène est de 1, 51 angstrom, tandis que dans le trioxyde de soufre, la longueur de la liaison soufre-oxygène est de 1, 42 angstrom. Ainsi, dans la molécule hybride, la longueur de liaison est un intermédiaire entre les liaisons simples et doubles. Dans les molécules hybrides, les électrons participant à des liaisons doubles ou à des paires solitaires sont souvent délocalisés sur plusieurs liaisons ou atomes, ce qui signifie qu'ils ne sont pas stationnaires sur un atome particulier.La délocalisation réduit l'énergie potentielle des électrons entraînant une stabilisation appelée stabilisation par résonance. La résonance est également observée pour les composés aromatiques tels que le benzène. Le benzène est un cycle de carbone hexagonal avec un hydrogène lié à chacun des atomes de carbone, et alternant des liaisons simples et doubles entre les atomes de carbone.Basé sur l'emplacement des doubles liaisons carbone-carbone, le benzène peut avoir deux structures de résonance. Rappelons que les obligations doubles sont généralement plus courtes que les obligations simples. Cependant, toutes les liaisons carbone-carbone dans le benzène ont des longueurs de liaison égales, qui sont intermédiaires entre les liaisons carbone-carbone simples et doubles.Le benzène, par conséquent, existe comme un hybride de résonance et peut être représenté comme un hexagone avec un cercle à l'intérieur. Le cercle indique que le benzène est un mélange de deux structures de résonance, et les doubles liaisons ne peuvent pas être localisées à deux atomes de carbone spécifiques.

mésomérie

La structure de Lewis d'un anion nitrite (NO2−) peut en fait être dessinée de deux façons différentes, qui se distinguent par les localisations des liaisons N-O et N=O.  
 
 <img alt="Figure1" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;" />
 
 Si les ions nitrites contenaient effectivement une liaison simple et une liaison double, les deux longueurs de liaison devraient être différentes. Une liaison double entre deux atomes est plus courte (et plus forte) qu'une liaison simple entre les deux mêmes atomes. Cependant, les expériences montrent que les deux liaisons N–O de NO2− ont la même force et la même longueur, et elles sont identiques d'après toutes les autres propriétés. Il n'est pas possible d'écrire une seule structure de Lewis pour NO2− dans laquelle l'azote a un octet et les deux liaisons sont équivalentes. 
 
 Au lieu de cela, le concept de mésomérie est utilisé : si deux ou plusieurs structures de Lewis avec la même disposition d'atomes peuvent être écrites pour une molécule ou un ion, la distribution réelle des électrons est une moyenne de celle indiquée par les diverses structures de Lewis. La distribution réelle des électrons dans chacune des liaisons azote-oxygène de NO2− est la moyenne d'une liaison double et d'une liaison simple.  
 
 Les structures de Lewis individuelles sont appelées des formes de résonance. La structure électronique réelle de la molécule (la moyenne des formes de résonance) est appelée un hybride de résonance des formes de résonance individuelles. Une flèche gauche droite entre les structures de Lewis indique qu'il s'agit de formes de résonance. 
 
 <img alt="Figure2" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;" />
 
 L'anion carbonate CO32− fournit un second exemple de résonance.  
 
 <img alt="Figure3" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;" />
 
 <ul>
 <li>Un atome d'oxygène doit avoir une double liaison avec un carbone pour compléter l'octet sur l'atome central.  </li>
 <li>Tous les atomes d'oxygène, cependant, sont équivalents et la liaison double pourrait se former à partir de n'importe lequel des trois atomes. Cela donne lieu à trois formes de résonance de l'ion carbonate.  </li>
 <li>Puisque trois structures de résonance identiques peuvent être écrites, on sait que la disposition réelle des électrons dans l'ion carbonate est la moyenne des trois structures.  </li>
 <li>Encore une fois, les expériences montrent que les trois liaisons C–O sont exactement les mêmes. </li>
 </ul>
 
 Il convient de toujours se rappeler qu'une molécule décrite comme un hybride de résonance ne possède jamais la structure électronique décrite par l'une ou l'autre forme de résonance. Il ne fluctue pas entre les formes de résonance ; la structure électronique réelle est toujours la moyenne de celle indiquée par toutes les formes de résonance.  
 
 George Wheland, l'un des pionniers de la théorie sur la résonance, a utilisé une analogie historique pour décrire la relation entre les formes de résonance et les hybrides de résonance. Un voyageur médiéval, n'ayant jamais vu un rhinocéros auparavant, l'a décrit comme l'hybride d'un dragon et d'une licorne parce qu'il avait beaucoup de propriétés en commun avec les deux. Tout comme un rhinocéros n'est ni un dragon parfois ni une licorne à d'autres moments, un hybride de résonance n'est aucune de ses formes de résonance à un moment donné. 
 
 Comme un rhinocéros, c'est une véritable entité et les preuves expérimentales ont montré qu'elle existe. Elle a certaines caractéristiques en commun avec ses formes de résonance, mais les formes de résonance elles-mêmes sont des images pratiques et imaginaires (comme la licorne et le dragon). 
 
 Ce texte est adapté de <a href="https://openstax.org/books/chemistry-2e/pages/7-4-formal-charges-and-resonance">Openstax, Chimie 2e, Section 7.4 : Charges formelles et résonance.</a>

Mésomérie

La structure de Lewis d’un anion nitrite (NO2−) peut en fait être dessinée de deux manières différentes, distinguées par les emplacements des N-O et 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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