Name: resonance forms in lewis structures
Uploaded: 2020-09-03T13:38:28.000Z
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PS.Chm.3.1

Resonance

Die meisten Moleküle und Ionen lassen sich durch einzigartige Lewis-Strukturen darstellen. Bestimmte Verbindungen können jedoch durch mehrere, gleichwertige Lewis-Strukturen dargestellt werden. Betrachten Sie die Lewis-Struktur für Schwefeltrioxid.Die Einzelbindungen zwischen jedem Sauerstoff und den zentralen Schwefelatomen erfüllen das Oktett für die Sauerstoffatome. Um jedoch ein volles Oktett für den Schwefel zu erreichen, muss eine zusätzliche Bindung zwischen dem Schwefel und einem der Sauerstoffatome gebildet werden. Da jeder der drei Sauerstoffatome eine Doppelbindung mit Schwefel bilden kann, kann man drei verschiedene Lewis-Strukturen zeichnen.Diese mehrfachen Lewis-Strukturen werden als Resonanzstrukturen bezeichnet, bei denen die Skelettstrukturen gleich bleiben, jedoch die Elektronen unterschiedlich verteilt sind. Alle drei Strukturen sind gültige und äquivalente Darstellungen des Moleküls, dennoch existieren sie nicht der Natur. Die eigentliche Struktur oszilliert nicht zwischen den Resonanzstrukturen, sondern ist ein Hybrid oder ein Mittelwert der drei Lewis-Strukturen, die in Bindungslängen gemessen werden können.In Sulfit beträgt die Länge einer Schwefel-Sauerstoff-Einfachbindung 1, 51 Angström, während in Schwefeltrioxid die Schwefel-Sauerstoff-Bindungslänge 1, 42 Angström beträgt. Im Hybridmolekül ist also die Bindungslänge ein Zwischenprodukt zwischen Einfach und Doppelbindungen. In Hybridmolekülen sind Elektronen, die an Doppelbindungen oder Einzelpaaren beteiligt sind, oft über mehrere Bindungen oder Atome verteilt, d.h.sie sind nicht fest an ein bestimmtes Atom gebunden. Diese Verteilung reduziert die potenzielle Energie der Elektronen, was zu einer Stabilisierung führt, die als Resonanzstabilisierung bezeichnet wird. Resonanz wird auch bei Aromaten wie Benzol beobachtet.Benzol ist ein hexagonaler Kohlenstoffring mit jeweils einem gebundenem Wasserstoff pro Kohlenstoffatom, und abwechselnden Einfach-und Doppelbindungen zwischen den Kohlenstoffatomen. Je nach der Position der Kohlenstoff-Kohlenstoff Doppelbindungen kann Benzol zwei Resonanzstrukturen aufweisen. Bedenken Sie, dass Doppelbindungen in der Regel kürzer als Einfachbindungen sind.Alle Kohlenstoff-Kohlenstoff Bindungen in Benzol haben jedoch gleiche Bindungslängen, die zwischen Kohlenstoff-Kohlenstoff Einfach-und Doppelbindungen liegen. Benzol liegt daher als Resonanzhybrid vor und kann als Sechseck mit einem Kreis im Inneren dargestellt werden. Der Kreis zeigt an, dass Benzol eine Mischung aus zwei Resonanzstrukturen ist und dass die Doppelbindungen nicht an zwei bestimmten Kohlenstoffatomen verteilt sind.

resonanz

Die Lewis-Struktur eines Nitritanions (NO2−) kann auf zwei verschiedene Arten dargestellt werden, die sich durch die Lage der N-O- und N=O-Bindungen unterscheiden. <img alt="Figure1" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;"> Wenn Nitritionen tatsächlich eine Einfach- und eine Doppelbindung enthalten, wäre zu erwarten, dass die beiden Bindungslängen unterschiedlich sind. Eine Doppelbindung zwischen zwei Atomen ist kürzer (und stärker) als eine Einfachbindung zwischen denselben beiden Atomen. Experimente zeigen jedoch, dass beide N-O-Bindungen in NO2− die gleiche Stärke und Länge haben und auch in allen anderen Eigenschaften identisch sind. Es ist allerdings nicht möglich, eine einzige Lewis-Struktur für NO2− zu schreiben, in der Stickstoff ein Oktett hat und beide Bindungen äquivalent sind. Stattdessen wird das Konzept der Resonanz verwendet: Wenn zwei oder mehr Lewis-Strukturen mit der gleichen Atomanordnung für ein Molekül oder Ion geschrieben werden können, ist die tatsächliche Elektronenverteilung ein Durchschnitt der verschiedenen Lewis-Strukturen. Die tatsächliche Elektronenverteilung in jeder der Stickstoff-Sauerstoff-Bindungen in NO2− ist der Durchschnitt einer Doppelbindung und einer Einfachbindung. Die einzelnen Lewis-Strukturen werden dann Resonanzformen genannt. Die tatsächliche elektronische Struktur des Moleküls (der Durchschnitt der Resonanzformen) wird als Resonanzhybrid der einzelnen Resonanzformen bezeichnet. Ein Doppelpfeil zwischen Lewis-Strukturen zeigt an, dass es sich um Resonanzformen handelt. <img alt="Figure2" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;"> Das Carbonatanion CO32− ist ein zweites Beispiel für eine Resonanzform. <img alt="Figure3" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;"> <ul> <li>Ein Sauerstoffatom muss eine Doppelbindung an einen Kohlenstoff haben, um das Oktett am Zentralatom zu vervollständigen.</li> <li>Alle Sauerstoffatome sind jedoch gleichwertig und die Doppelbindung könnte aus jedem der drei Atome entstehen. Dadurch entstehen drei Resonanzformen des Carbonations.</li> <li>Da drei identische Resonanzstrukturen geschrieben werden können, ist die tatsächliche Anordnung der Elektronen im Carbonation gleich dem Durchschnitt der drei Strukturen.</li> <li>Auch hier zeigen Experimente, dass alle drei C–O-Bindungen genau gleich sind.</li> </ul> Denken Sie immer daran, dass ein als Resonanzhybrid beschriebenes Molekül niemals eine elektronische Struktur besitzt, die durch nur eine der beiden Resonanzformen beschrieben wird. Es schwankt nicht zwischen Resonanzformen; Vielmehr ist die tatsächliche elektronische Struktur immer der Durchschnitt aller Resonanzformen. George Wheland, einer der Pioniere der Resonanztheorie, nutzte eine historische Analogie, um die Beziehung zwischen Resonanzformen und Resonanzhybriden zu beschreiben. Ein mittelalterlicher Reisender, der noch nie zuvor ein Nashorn gesehen hatte, beschrieb es als eine Mischung aus einem Drachen und einem Einhorn, weil es mit beiden viele Eigenschaften gemeinsam hatte. So wie ein Nashorn weder manchmal ein Drache noch manchmal ein Einhorn ist, ist ein Resonanzhybrid zu keinem Zeitpunkt eine einzige seiner Resonanzformen. Wie ein Nashorn ist es ein reales Wesen, dessen Existenz experimentell nachgewiesen wurde. Es hat einige Eigenschaften mit seinen Resonanzformen gemeinsam, aber die Resonanzformen selbst sind nur praktische, imaginäre Bilder (wie das Einhorn und der Drache). Dieser Text wurde adaptiert von <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>

Resonanz

Die Lewis-Struktur eines Nitrit-Anions (NO2−) kann tatsächlich auf zwei verschiedene Arten gezeichnet werden, die sich durch die Positionen von N-O und 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

types of chemical bonds

Chemical Bonding and Bond Properties

Chemical bonding explains how atoms and ions join to form molecules and compounds. American chemist Gilbert N. Lewis pioneered chemical bonding theory with the Lewis model. This model helps explain why bonds form, why some are stronger than others, and why compounds have fixed formulas like H2O instead of H4O. Ionic bonding involves ions, which are atoms or molecules with an electrical charge. A cation is a positive ion formed when a neutral atom loses one or more electrons from its valence...

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covalent bonding and lewis structures

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Drawing Lewis Structures with Valence Electron Counts

Drawing Lewis structures starts with counting valence electrons and building the atom arrangement step by step. Valence electrons are the outer-shell electrons that help show how atoms bond. For ions, a positive charge means one electron is removed for each plus sign, and a negative charge means one electron is added for each minus sign. The next step is to sketch the skeleton structure. The least electronegative atom usually goes in the center, while hydrogen is almost never central. Fluorine...

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...

formal charges

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key terms and concepts

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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