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

يمكن تمثيل معظم الجزيئات والأيونات باستخدام بنية لويس الفريدة. ومع ذلك،يمكن أن يكون لبعض المركبات بنية لويس متعددة ومتساوية الصلاحية. ضع في اعتبارك،بنية لويس لثالث أكسيد الكبريت.الروابط الفردية بين كل من الأكسجين وذرة الكبريت المركزية تكمل الثمانية بالنسبة لذرات الأكسجين. ومع ذلك،للوصول إلى ثمانية كاملة للكبريت،يجب تكوين رابطة إضافية،بين الكبريت وواحدة من ذرات الأكسجين. نظرًا لأن أيًا من ذرات الأكسجين الثلاثة يمكن أن يشكل رابطة مزدوجة مع الكبريت،يمكن استخلاص ثلاثة من بنية لويس مختلفين.بنية لويس المتعددة هذه،هي ما تسمى هياكل الرنين،حيث التركيبات الهيكلية تظل كما هي،لكن يتم توزيع الإلكترونات بشكل مختلف. جميع الهياكل الثلاثة هي تمثيلات صحيحة ومتكافئة من الجزيء،ومع ذلك كلها غير موجودة في الطبيعة. البنية الفعلية،لا تتأرجح بين هياكل الرنين،لكنها هجينة أو هي متوسط لبنيات لويس الثلاثة،و يمكن قياسها بأطوال الروابط.في الكبريتيت،طول الرابطة الأحادية الكبريت-الأكسجين هو 1.51 أنجستروم،بينما في ثالث أكسيد الكبريت،يبلغ طول رابطة الكبريت-الأكسجين 1.42 أنجستروم. وهكذا،في الجزيء الهجين،طول الرابطة هو متوسط بين الروابط الفردية والثنائية. في الجزيئات الهجينة،تشارك الإلكترونات في روابط ثنائية أو تكون الأزواج المفردة غالبًا غير متمركزة على روابط أو ذرات متعددة،مما يعني أنها ليست ثابتة على ذرة معينة.يقلل عدم التمركز من الطاقة الكامنة للإلكترونات مما يؤدي إلى الاستقرار،ويسمى استقرار الرنين. كما لوحظ وجود رنين للمركبات العطرية مثل البنزين. البنزين عبارة عن حلقة كربونية سداسية،مع هيدروجين واحد مرتبط بكل ذرة من ذرات الكربون،و روابط فردية و ثنائية متناوبة،بين ذرات الكربون.بناءًعلى موقع الروابط الثنائية بين الكربون والكربون،يمكن أن يكون للبنزين هيكلين رنين. تذكر أن الروابط المزدوجة عادة ما تكون أقصر من الروابط المفردة. ومع ذلك،فإن جميع روابط الكربون-الكربون،في البنزين،لها أطوال روابط متساوية،وهي متوسطة بين روابط الكربون-الكربون المفردة و الروابط الثنائية.ومن ثم،يوجد البنزين باعتباره هجينًا رنينيًا ويمكن تمثيله كحلقة سداسية بداخلها دائرة. تشير الدائرة إلى أن البنزين هو مزيج من اثنين من هياكل الرنين،والروابط المزدوجة لا يمكن أن تكون متمركزة بين أي ذرتين محددتين من الكربون.

الرنين

يمكن رسم بنية لويس لأنيون النتريت (NO2−) بطريقتين مختلفتين، يتم تمييزهما بمواقع الروابط N-O و N=O . <img alt="Figure1" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;" /> إذا كانت أيونات النتريت تحتوي بالفعل على رابطة مفردة ومزدوجة، فمن المتوقع أن يكون طولا الرابطة مختلفين. الرابطة المزدوجة بين ذرتين أقصر (وأقوى) من رابطة واحدة بين نفس الذرتين. ومع ذلك، أظهرت التجارب أن كلا من الروابط N–O في NO2− لهما نفس القوة والطول، وهما متطابقين في جميع الخصائص الأخرى. لا يمكن كتابة بنية لويس واحدة لـ NO2− حيث يحتوي النيتروجين على مجموعة ثمانية وكلا الروابط متكافئة. بدلاً من ذلك، يتم استخدام مفهوم الرنين: إذا كان من الممكن كتابة اثنين أو أكثر من بنى لويس لها نفس ترتيب الذرات لجزيء أو أيون، فإن التوزيع الفعلي للإلكترونات يكون متوسط لذلك التي أظهرتها هياكل لويس المختلفة. التوزيع الفعلي للإلكترونات في كل من روابط نيتروجين-أكسجين في NO2− هو متوسط ​​الرابطة المزدوجة والرابطة الفردية.   تسمى تراكيب لويس الفردية بأشكال الرنين. يُطلق على التركيب الإلكتروني الفعلي للجزيء (متوسط ​​أشكال الرنين) هجين رنين لأشكال الرنين الفردية. يشير سهم برأسين بين هياكل لويس إلى أنها أشكال رنين. <img alt="Figure2" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;" /> أنيون الكربونات، CO32−، يقدم مثالاً ثانياً على الرنين. <img alt="Figure3" src="https://www.jovecore.com/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;" /><ul><li> يجب أن تحتوي ذرة أكسجين واحدة على رابطة مزدوجة مع الكربون لإكمال المجموعة الثمانية على الذرة المركزية. </li><li> ومع ذلك، فإن جميع ذرات الأكسجين متساوية، ويمكن أن تتكون الرابطة المزدوجة من أي ذرة من الذرات الثلاث. هذا يؤدي إلى ظهور ثلاثة أشكال رنين لأيون الكربونات. & nbsp؛ </li><li> نظراً لأنه يمكن كتابة ثلاثة هياكل رنين متطابقة، فمن المعروف أن الترتيب الفعلي للإلكترونات في أيون الكربونات هو متوسط ​​الهياكل الثلاثة. </li><li> مرة أخرى، تظهر التجارب أن جميع روابط C–O الثلاثة متطابقة تماماً. </li></ul> تذكر دائماً أن الجزيء الموصوف على أنه هجين رنين أبداً لا يمتلك بنية إلكترونية موصوفة بأي من شكلي الرنين. لا يتأرجح بين أشكال الرنين؛ بدلاً من ذلك، فإن البنية الإلكترونية الفعلية هي دائمًا متوسط ​​ما تظهره جميع أشكال الرنين. استخدم جورج ويلاند، أحد رواد نظرية الرنين، تشبيهاً تاريخياً لوصف العلاقة بين أشكال الرنين وهجائن الرنين. مسافر من العصور الوسطى، لم ير قط وحيد القرن من قبل، يمكن أن يصفه بأنه هجين من تنين ووحيد القرن لأن له العديد من الخصائص المشتركة مع كليهما. تماماً كما أن وحيد القرن ليس تنيناً في بعض الأحيان ولا وحيد القرن في أوقات أخرى ، فإن الهجين الرنيني ليس من أشكال الرنين الخاصة به في أي وقت. مثل وحيد القرن، إنه كيان حقيقي أثبت الدليل التجريبي وجوده. تشترك في بعض الخصائص مع أشكال الرنين، لكن أشكال الرنين نفسها هي صور ملائمة وخيالية (مثل وحيد القرن والتنين). هذا النص مقتبس من <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>

يمكن رسم هيكل لويس لأنيون النتريت (NO2−) بطريقتين مختلفتين ، تتميز بمواقع N-O و N = O ...

Education

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واحد

Chemical Bonding: Basic Concepts

الترابط الكيميائي: مفاهيم أساسية

KEY TERMS AND CONCEPTS

المصطلحات والمفاهيم الأساسية

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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ionic bonding and electron transfer

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Lattice energy shows how strongly ions hold an ionic solid together. It is the energy required to separate one mole of a solid into its gaseous ions. For sodium chloride, this process requires 769 kJ per mole. The opposite convention may also be used, where lattice energy is the energy released when gaseous ions form the solid. In either case, a larger magnitude means a more stable ionic compound. For ionic crystals, lattice energy follows a pattern based on charge and ion size. The...

covalent bonding and lewis structures

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lewis structures of molecular compounds and polyatomic ions

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Drawing Lewis Structures with Valence Electron Counts

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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...

formal charges

Lewis Structures with Formal Charge

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exceptions to the octet rule

Octet Rule Exceptions in Lewis Structures

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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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	...

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Surface Tension, Capillary Action, and Viscosity

Surface Tension
The various IMFs between identical molecules of a substance are examples of cohesive forces. The molecules within a liquid are surrounded ...

Construct an explanation to summarize the influences intermolecular forces have on the properties of chemical compounds.

PS.Chm.3.2

Analyze the structure of atoms and isotopes.

Resonance Forms in Lewis Structures

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