Name: resonance forms in lewis structures
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Resonance

De meeste moleculen en ionen kunnen worden weergegeven met behulp van unieke Lewis-structuren. Bepaalde verbindingen kunnen echter worden aangetoond door meerdere, even geldige Lewis-structuren. Zoals de Lewis-structuur voor zwaveltrioxide.De enkele bindingen tussen elk zuurstof en de centrale zwavelatomen voldoen aan het octet voor zuurstofatomen. Om echter een volledig octet voor de zwavel te bereiken, moet een extra binding worden gevormd tussen zwavel en een van de zuurstofatomen. Omdat elk van de drie zuurstofatomen de dubbele binding met zwavel kan vormen, kunnen drie verschillende Lewis-structuren worden getekend.Deze meervoudige Lewis-structuren worden resonantiestructuren genoemd, waarbij de skeletstructuren hetzelfde blijven, maar elektronen anders worden verdeeld. Alle drie de structuren zijn geldige en gelijkwaardige representaties van het molecuul, maar ze zijn allemaal niet aanwezig in de natuur. De feitelijke structuur oscilleert niet tussen de resonantiestructuren, maar is een hybride of een gemiddelde van de drie Lewis-structuren, die kan worden gemeten in bindingslengtes.Bij sulfiet is de lengte van een enkelvoudige zwavel-zuurstofbinding 1, 51 ångström, terwijl bij zwaveltrioxide de lengte van de zwavel-zuurstofbinding 1, 42 ångström is. In het hybride molecuul is de bindingslengte dus een intermediair tussen enkele en dubbele bindingen. In hybride moleculen worden elektronen die deelnemen aan dubbele bindingen of vrije paren vaak gedelokaliseerd over meerdere bindingen of atomen, wat betekent dat ze niet stationair zijn op één bepaald atoom.De delokalisatie vermindert de potentiële energie van elektronen, wat resulteert in stabilisatie die resonantiestabilisatie wordt genoemd. Resonantie wordt ook waargenomen voor aromatische verbindingen zoals benzeen. Benzeen is een hexagonale koolstofring met één waterstof gebonden aan elk van de koolstofatomen en afwisselend enkele en dubbele bindingen tussen de koolstofatomen.Gebaseerd op de locatie van dubbele koolstof-koolstofbindingen, kan benzeen twee resonantiestructuren hebben. Bedenk dat dubbele bindingen meestal korter zijn dan enkele bindingen. Alle koolstof-koolstofbindingen in benzeen hebben echter dezelfde bindingslengtes, die tussen enkele en dubbele koolstof-koolstofbindingen liggen.Benzeen bestaat daarom als een resonantiehybride en kan worden weergegeven als een zeshoek met een cirkel erin. De cirkel geeft aan dat benzeen een mengsel is van twee resonantiestructuren en dat de dubbele bindingen niet kunnen worden gelokaliseerd op twee specifieke koolstofatomen.

resonantie

De Lewis-structuur van een nitrietanion (NO2−) kan feitelijk op twee verschillende manieren worden getekend, te onderscheiden door de locaties van de N-O- en N=O-bindingen. <img alt="Figure1" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;"> Als nitrietionen inderdaad een enkele en een dubbele binding bevatten, wordt verwacht dat de twee bindingslengtes verschillend zijn. Een dubbele binding tussen twee atomen is korter (en sterker) dan een enkele binding tussen dezelfde twee atomen. Experimenten tonen echter aan dat beide N–O-bindingen in NO2− dezelfde sterkte en lengte hebben, en identiek zijn in alle andere eigenschappen. Het is niet mogelijk om één enkele Lewis-structuur voor NO2− te schrijven waarin stikstof een octet heeft en beide bindingen equivalent zijn. In plaats daarvan wordt het concept van resonantie gebruikt: als twee of meer Lewis-structuren met dezelfde rangschikking van atomen kunnen worden geschreven voor een molecuul of ion, is de feitelijke verdeling van elektronen een gemiddelde van die weergegeven door de verschillende Lewis-structuren. De werkelijke verdeling van elektronen in elk van de stikstof-zuurstofbindingen in NO2− is het gemiddelde van een dubbele binding en een enkele binding. De individuele Lewis-structuren worden resonantievormen genoemd. De feitelijke elektronische structuur van het molecuul (het gemiddelde van de resonantievormen) wordt een resonantiehybride van de individuele resonantievormen genoemd. Een tweepuntige pijl tussen Lewis-structuren geeft aan dat het resonantievormen zijn. <img alt="Figure2" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;"> Het carbonaatanion, CO32−, is een tweede voorbeeld van resonantie. <img alt="Figure3" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;"> <ul> <li>Eén zuurstofatoom moet een dubbele binding met een koolstofatoom hebben om het octet op het centrale atoom te voltooien.</li> <li>Alle zuurstofatomen zijn echter gelijkwaardig en de dubbele binding kan uit elk van de drie atomen ontstaan. Dit geeft aanleiding tot drie resonantievormen van het carbonaation.</li> <li>Omdat er drie identieke resonantiestructuren kunnen worden geschreven, is het bekend dat de feitelijke rangschikking van elektronen in het carbonaation het gemiddelde is van de drie structuren.</li> <li>Opnieuw tonen experimenten aan dat alle drie de C-O-bindingen precies hetzelfde zijn.</li> </ul> Onthoud altijd dat een molecuul dat wordt beschreven als een resonantiehybride nooit een elektronische structuur bezit die door een van beide resonantievormen wordt beschreven. Het fluctueert niet tussen resonantievormen; de feitelijke elektronische structuur is eerder altijd het gemiddelde van dat wat door alle resonantievormen wordt getoond. George Wheland, een van de pioniers van de resonantietheorie, gebruikte een historische analogie om de relatie tussen resonantievormen en resonantiehybriden te beschrijven. Een middeleeuwse reiziger, die nog nooit eerder een neushoorn had gezien, beschreef hem als een hybride van een draak en een eenhoorn, omdat hij veel eigenschappen met beide gemeen had. Net zoals een neushoorn soms geen draak is en soms ook geen eenhoorn, is een resonantiehybride op geen enkel moment een van zijn resonantievormen. Net als een neushoorn is het een echte entiteit waarvan experimenteel bewijs heeft aangetoond dat het bestaat. Het heeft enkele kenmerken gemeen met zijn resonantievormen, maar de resonantievormen zelf zijn handige, denkbeeldige afbeeldingen (zoals de eenhoorn en de draak). Deze tekst is aangepast van <a href="https://openstax.org/books/chemistry-2e/pages/7-4-formal-charges-and-resonance">Openstax, Chemistry 2e, Sectie 7.4: Formele Ladingen en Resonantie.</a>

Resonantie

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 ...

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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.

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Resonance Forms in Lewis Structures

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