Name: resonance forms in lewis structures
Uploaded: 2020-09-03T13:38:28.000Z
Duration: 2 min 52 s
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North Carolina K-12 Science Standard Course of Study

9-12

Chemistry

Matter and its Interactions

PS.Chm.3.1

Resonance

Większość cząsteczek i jonów można przedstawić za pomocą unikalnych struktur Lewisa. Jednak pewne związki mogą być pokazane przez wiele, równie ważnych struktur Lewisa. 

Rozważ strukturę Lewisa dla trójtlenku siarki. Pojedyncze wiązania między każdym tlenem a centralnymi atomami siarki spełniają oktet dla atomów tlenu. Jednak, aby osiągnąć pełny oktet siarki, musi zostać utworzone dodatkowe wiązanie między siarką a jednym z atomów tlenu. Ponieważ każdy z trzech tlenów może tworzyć podwójne wiązanie z siarką, można narysować trzy różne struktury Lewisa. 

Te liczne struktury Lewisa nazywane są strukturami rezonansowymi, w których struktury szkieletowe pozostają takie same, ale elektrony są inaczej rozmieszczone.

Wszystkie trzy struktury są prawomocnymi i równoważnymi reprezentacjami cząsteczki, ale wszystkie nie istnieją w naturze. Rzeczywista struktura nie oscyluje między strukturami rezonansowymi, ale jest hybrydą lub średnią z trzech struktur Lewisa, które można zmierzyć w długościach wiązań. 

W siarczynie długość pojedynczego wiązania siarka-tlen wynosi 1,51 angstrema, podczas gdy w trójtlenku siarki długość wiązania siarka-tlen wynosi 1,42 angstrema. Tak więc w cząsteczce hybrydowej długość wiązania jest pośrednia między wiązaniami pojedynczymi i podwójnymi. 

W cząsteczkach hybrydowych elektrony uczestniczące w wiązaniach podwójnych lub samotnych parach są często zdelokalizowane na wielu wiązaniach lub atomach, co oznacza, że nie są nieruchome na jednym konkretnym atomie. Delokalizacja zmniejsza energię potencjalną elektronów, powodując stabilizację zwaną stabilizacją rezonansową. 

Rezonans obserwuje się również w przypadku związków aromatycznych, takich jak benzen. Benzen jest sześciokątnym pierścieniem węglowym z jednym wodorem związanym z każdym z atomów węgla oraz naprzemiennymi pojedynczymi i podwójnymi wiązaniami między atomami węgla. W oparciu o lokalizację podwójnych wiązań węgiel-węgiel, benzen może mieć dwie struktury rezonansowe. 

Przypomnijmy, że wiązania podwójne są zwykle krótsze niż wiązania pojedyncze. Jednak wszystkie wiązania węgiel-węgiel w benzenie mają równe długości wiązań, które są pośrednie między pojedynczymi i podwójnymi wiązaniami węgiel-węgiel. 

W związku z tym benzen istnieje jako hybryda rezonansowa i może być reprezentowany jako sześciokąt z okręgiem w środku. Okrąg wskazuje, że benzen jest mieszanką dwóch struktur rezonansowych, a wiązania podwójne nie mogą być zlokalizowane w żadnych dwóch konkretnych atomach węgla.

rezonans

Strukturę Lewisa anionu azotynowego (NO2−) można w rzeczywistości narysować na dwa różne sposoby, z rozróżnieniem lokalizacji wiązań NO i N=O.

<img alt="Figure1" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;">

Jeśli jony azotynowe rzeczywiście zawierają wiązanie pojedyncze i podwójne, oczekuje się, że długości tych dwóch wiązań będą różne. Podwójne wiązanie między dwoma atomami jest krótsze (i silniejsze) niż pojedyncze wiązanie między tymi samymi dwoma atomami. Jednakże eksperymenty udowadniają, że oba wiązania N–O w NO2− mają tę samą siłę i długość oraz są identyczne we wszystkich pozostałych właściwościach. Nie jest możliwe przedstawienie pojedynczej struktury Lewisa dla NO2−, w której azot ma oktet i oba wiązania są równoważne.

Zamiast tego stosuje się koncepcję rezonansu: jeśli dla cząsteczki lub jonu można zapisać dwie lub więcej struktur Lewisa o tym samym układzie atomów, rzeczywisty rozkład elektronów jest średnią rozkładu pokazanego przez różne struktury Lewisa. Rzeczywisty rozkład elektronów w każdym wiązaniu azot-tlen w NO2− jest średnią wiązania podwójnego i wiązania pojedynczego.

Struktury Lewisa nazywane są formami rezonansowymi. Rzeczywista struktura elektronowa cząsteczki (średnia form rezonansowych) nazywana jest hybrydą rezonansową poszczególnych form rezonansowych. Dwustronna strzałka pomiędzy strukturami Lewisa wskazuje, że są to formy rezonansowe.

<img alt="Figure2" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;">

Anion węglanowy, CO32-, stanowi drugi przykład rezonansu.

<img alt="Figure3" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;">

Aby ukończyć oktet na atomie centralnym, jeden atom tlenu musi mieć podwójne wiązanie z węglem.

Jednakże wszystkie atomy tlenu są równoważne, a wiązanie podwójne może powstać z dowolnego z trzech atomów. Prowadzi to do powstania trzech form rezonansowych jonu węglanowego.

Ponieważ można zapisać trzy identyczne struktury rezonansowe, wiadomo, że rzeczywiste rozmieszczenie elektronów w jonie węglanowym jest średnią z trzech struktur.

Ponownie eksperymenty pokazują, że wszystkie trzy wiązania C – O są dokładnie takie same.

Zawsze pamiętaj, że cząsteczka opisana jako hybryda rezonansowa nigdy nie posiada struktury elektronowej opisanej przez którąkolwiek formę rezonansu. Nie waha się pomiędzy formami rezonansu, a raczej rzeczywista struktura elektronowa jest zawsze średnią struktury wykazywanej przez wszystkie formy rezonansu.

George Wheland, jeden z pionierów teorii rezonansu, posłużył się analogią historyczną do opisania związku pomiędzy formami rezonansowymi a hybrydami rezonansowymi. Średniowieczny podróżnik, który nigdy wcześniej nie widział nosorożca, opisał go jako hybrydę smoka i jednorożca, ponieważ miał z nimi wiele wspólnego. Tak jak nosorożec nie ani jednorożcem, ani smokiem, tak hybryda rezonansowa nie jest w żadnym momencie żadną ze swoich form rezonansowych.

Podobnie jak nosorożec, jest to realna istota, której istnienie wykazały eksperymenty. Ma pewne cechy wspólne z formami rezonansowymi, ale same formy rezonansowe są wygodnymi, wyimaginowanymi obrazami (jak jednorożec i smok).

Rezonans

Strukturę Lewisa anionu azotynowego (NO2−) można w rzeczywistości narysować na dwa różne sposoby, różniące się położeniem N-O i N=O ...

Education

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Chemical Bonding: Basic Concepts

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Kluczowe terminy i pojęcia

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.

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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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