Name: resonance forms in lewis structures
Uploaded: 2020-09-03T13:38:28.000Z
Duration: 2 min 52 s
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Chemistry

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PS.Chm.3.1

Resonance

רוב המולקולות והיונים יכולים להיות מיוצגים במבני לואיס ייחודיים. אך תרכובות מסוימות ניתנות לייצוג בכמה מבני לואיס, שכולם תקפים באותה מידה. לדוגמה, מבנה לואיס של גופרית תלת-חמצנית.הקשרים היחידים בין כל אטום חמצן ואטומי הגופרית המרכזיים משלימים אוקטט של אטומי החמצן. אך כדי להשלים אוקטט מלא בגופרית, חייב להיווצר קשר נוסף בין הגופרית ואחד מאטומי החמצן. כיוון שכל אחד משלושת אטומי החמצן יכול ליצור קשר כפול עם גופרית, יכולים להיווצר שלושה מבני לואיס שונים.מבני לואיס מרובים אלה נקראים מבני רזוננס"ובהם מבני השלד נשארים זהים, אבל אלקטרונים מפוזרים באופן אחר. כל שלושת המבנים הם ייצוגים תקפים ושווים של המולקולה, אבל כולם לא קיימים בטבע. המבנה בפועל לא מחליף צורה בין מבני הרזוננס, אלא הוא הכלאה או ממוצע של שלושת מבני לואיס, הניתן למדידה באמצעות אורכי קשר.בגופרית, אורכו של קשר יחיד של תחמוצת גופרית הוא 1.51 אנגסטרום בעוד שבגופרית תלת-חמצנית, אורך הקשר גופרית-חמצן הוא 1.42 אנגסטרום. לכן, במולקולה הממוצעת, אורך הקשר הוא בתווך בין קשר יחיד לכפול. במולקולות ממוצעות, אלקטרונים המהווים חלק מקשרים כפולים או יחידים מפוזרים על פני כמה קשרים או אטומים, כלומר, הם אינם קבועים על אטום מסוים.הפיזור מפחית את האנרגיה הפוטנציאלית של האלקטרונים, מה שמוביל ליציבות המכונה יציבות רזוננס"רזוננס נצפה גם בתרכובות ארומטיות כגון בנזן. בנזן הוא טבעת פחמן משושה שבה מימן אחד קשור לכל אחד אטומי הפחמן וקשרים יחידים וכפולים מתחלפים בין אטומי הפחמן. על סמך מיקומם של קשרי פחמן-פחמן כפולים, לבנזן יכולים להיות בשני מבני רזוננס.זכרו שקשרים כפולים הם בדרך כלל קצרים יותר מקשרים יחידים. אך לכל קשרי פחמן-פחמן בבנזין יש אורכי קשר זהים, הנמצאים בתווך בין קשרי פחמן-פחמן יחידים וכפולים. לכן, בנזין קיים כהכלאת רזוננס וניתן לייצוג כמשושה עם עיגול בפנים.העיגול מעיד על כך שהבנזין הוא תרכובת של שני מבני רזוננס, והקשרים הכפולים לא יכולים להיות ממוקמים בשני אטומי פחמן ספציפיים כלשהם.

תהודה

<div style="direction:rtl">ניתן לצייר את מבנה לואיס של אניון ניטריט (NO2−) בשתי דרכים שונות, מובחן על ידי מיקומי הקשרים N-O ו-N=O. <img alt="Fאיור 1" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_1.svg" style="height: 40px;"> אם יוני ניטריט אכן מכילים קשר יחיד וכפול, שני אורכי הקשר צפויים להיות שונים. קשר כפול בין שני אטומים קצר יותר (וחזק יותר) מקשר בודד בין אותם שני אטומים. עם זאת, ניסויים מראים שלשני קשרי ה-N–O ב-NO2− יש חוזק ואורך זהים, והם זהים בכל שאר המאפיינים. לא ניתן לכתוב מבנה לואיס בודד עבור NO2− שבו לחנקן יש אוקטטה ושני הקשרים שווים. במקום זאת, נעשה שימוש במושג תהודה: אם ניתן לכתוב שני מבני לואיס או יותר עם אותו סידור אטומים עבור מולקולה או יון, ההתפלגות בפועל של האלקטרונים היא ממוצע של זה שמוצג על ידי מבני לואיס השונים. ההתפלגות בפועל של אלקטרונים בכל אחד מקשרי החנקן-חמצן ב-NO2− היא הממוצע של קשר כפול וקשר בודד. המבנים הבודדים של לואיס נקראים צורות תהודה. המבנה האלקטרוני האמיתי של המולקולה (הממוצע של צורות התהודה) נקרא תהודה היברידית של צורות התהודה האישיות. חץ דו-ראשי בין מבני לואיס מצביע על כך שהם צורות התהודה. <img alt="איור 2" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_2.svg" style="height: 40px;"> האניון הקרבונט, CO32−, מספק דוגמה שנייה לתהודה. <img alt="איור 3" src="https://www.jove.com/files/core/CDNSource/lessons/1064/1064Image_3.svg" style="height: 80px;"> <ul style="padding-right: 35px; list-style-type: disc;"> <li style="text-align: right;">לאטום חמצן אחד חייב להיות קשר כפול לפחמן כדי להשלים את האוקטטה באטום המרכזי.</li> <li style="text-align: right;">עם זאת, כל אטומי החמצן שווים, והקשר הכפול יכול להיווצר מכל אחד משלושת האטומים. זה גורם לשלוש צורות תהודה של יון הקרבונט.</li> <li style="text-align: right;">מכיוון שניתן לכתוב שלושה מבני תהודה זהים, ידוע כי סידור האלקטרונים בפועל ביון הקרבונט הוא הממוצע של שלושת המבנים.</li> <li style="text-align: right;">שוב, ניסויים מראים שכל שלושת קשרי ה-C–O זהים לחלוטין.</li> </ul> זכרו תמיד שלמולקולה המתוארת כתהודה היברידית לעולם אין מבנה אלקטרוני המתואר בשתי צורות התהודה. זה לא משתנה בין צורות תהודה; במקום זאת, המבנה האלקטרוני בפועל הוא תמיד הממוצע של זה שמוצג על ידי כל צורות התהודה. ג'ורג' ווילנד, אחד מחלוצי תורת התהודה, השתמש באנלוגיה היסטורית כדי לתאר את הקשר בין צורות תהודה ותהודה היברידית. נוסע מימי הביניים, שמעולם לא ראה קרנף, תיאר אותו כהיבריד של דרקון וחד קרן, כי היו לו תכונות משותפות רבות עם שניהם. כמו שלפעמים קרנף אינו דרקון או חד קרן בזמנים אחרים, תהודה היברידית אינה אף אחת מצורות התהודה שלו בכל זמן נתון. כמו קרנף, זוהי ישות אמיתית שראיות ניסיוניות הוכיחו שהיא קיימת. יש לו כמה מאפיינים משותפים עם צורות התהודה שלו, אבל צורות התהודה עצמן הן דימויים נוחים, ודמיוניים (כמו החד קרן והדרקון). טקסט זה מותאם מ <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></div>

מבנה לואיס של אניון ניטריט (NO2−) יכול למעשה להיות משורטט בשתי דרכים שונות, המובחנות על ידי המיקומים של N-O ו- 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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lewis structures of molecular compounds and polyatomic ions

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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

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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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The absolute value of the difference in electronegativity (&Delta;EN) of two bonded atoms provides a rough measure of the polarity to be ...

Lewis Structures of Molecular Compounds and Polyatomic Ions

To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:


	Determine the ...

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 ...

Formal Charges

In some cases, there are seemingly more than one valid Lewis structures for molecules and polyatomic ions. The concept of formal charges can be used to ...

Exceptions to the Octet Rule

Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:


	...

Bond Energies and Bond Lengths

Stable molecules exist because covalent bonds hold the atoms together. The strength of a covalent bond is measured by the energy required to break it, ...

Analyze and interpret data to explain the mechanisms and properties of the two main types of intramolecular (ionic and covalent) bonds.

molecular-comparison-of-gases-liquids-and-solids

Molecular Comparison of Gases, Liquids, and Solids

Particles in a solid are tightly packed together (fixed shape) and often arranged in a regular pattern; in a liquid, they are close together with no ...

Intermolecular vs Intramolecular Forces

Intermolecular forces (IMF) are electrostatic attractions arising from charge-charge interactions between molecules. The strength of the intermolecular ...

Intermolecular Forces

Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions ...

comparing-intermolecular-forces-melting-point-boiling-point

Comparing Intermolecular Forces: Melting Point, Boiling Point, and Miscibility

Intermolecular forces are attractive forces that exist between molecules. They dictate several bulk properties, such as melting points, boiling points, ...

surface-tension-capillary-action-and-viscosity

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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