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elocalization and Resonance

Structures

Rules
In resonance structures, the electrons are able to move to help stabilize the molecule. This movement of the
electrons is calleddelocalization.
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Resonance structures should have the same number of electrons, do not add or subtract any electrons.
(You can check the number of electrons by counting them)
All resonance structures must follow the rules of writing Lewis Structures.
The hybridization of the structure must stay the same.
The skeleton of the structure can not be changed (only the electrons move).
Resonance structures must also have the same amount of lone pairs.

Formal Charge
Even though the structures look the same, the formal charge (FC) may not be. Formal charges are charges that are
assigned to a specific atom in a molecule. If computed correctly, the overall formal charge of the molecule should be
the same as the oxidation charge of the molecule (the charge when you write out the empirical and molecular
formula) We want to choose the resonance structure with the least formal charges that add up to zero or the charge
of the overall molecule.
The equation for finding Formal Charge is:
Formal Charge = (number of valence electrons in free orbital) - (number of lone-pair electrons) - ( \( \frac{1}{2}
\) number bond pair electrons)
The formal charge has to equal the molecule's overall charge.
Ex.) CNS- has an overall charge of -1, so the Lewis structure's formal charge has to equal -1.
See Lewis Structure for more information.

Example 2: Thiocyanate Ion


Consider the thiocyanate (CNS-) ion.
SOLUTION
1. Find the Lewis Structure of the molecule. (Remember the Lewis Structure rules.)

2. Resonance: All elements want an octet, and we can do that in multiple ways by moving the terminal atom's electrons around (bonds too).

3. Assign Formal Charges


Formal Charge = (number of valence electrons in free orbital) - (number of lone-pair electrons) - ( \( \frac{1}{2} \) number bond pair electrons)
Remember to determine the number of valence electron each atom has before assigning Formal Charges
C = 4 valence e-, N = 5 valence e-, S = 6 valence e-, also add an extra electron for the (-1) charge. The total of valence electrons is 16.

4. Find the most ideal resonance structure. (Note: It is the one with the least formal charges that adds up to zero or to the molecule's overall charge.)

5. Now we have to look at electronegativity for the "Correct" Lewis structure.


The most electronegative atom usually has the negative formal charge, while the least electronegative atom usually has the positive formal charges.

Resonance Hybrids
Resonance Structures are a representation of a Resonance Hybrid, which is the combination of all resonance
structures. Though the Formal Charge closest to zero is the most accepted structure, in reality the correct Lewis
structure is actually a combination of all the resonance structures (and hence is not solely describe as one).
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Draw the Lewis Structure & Resonance for the molecule (using solid lines for bonds).
Where there can be a double or triple bond, draw a dotted line (-----) for a bond.
Draw only the lone pairs found in all resonance structures, do not include the lone pairs that are not on all of
the resonance structures.

Example 3: Carbonate Ion


Consider the carbonate ion: CO32SOLUTION

Step 1: Draw the Lewis Structure & Resonance.

Step 2: Combine the resonance structures by adding (dotted) bonds where other resonance bonds can be formed.

Step 3: Add only the lone pairs found on ALL resonance structures.

The bottom is the finished resonance hybrid for CO32-.

Rules for estimating stability of resonance


structures
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The greater the number of covalent bonds, the greater the stability since more atoms will have complete
octets

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The structure with the least number of formal charges is more stable
The structure with the least separation of formal charge is more stable
A structure with a negative charge on the more electronegative atom will be more stable
Positive charges on the least electronegative atom (most electropositive) is more stable
Resonance forms that are equivalent have no difference in stability and contribute equally. (eg.
benzene)

Example 4: Other Examples

The above resonance structures show that the electrons are delocalized within the molecule and through this process the molecule gains extra stabil
Ozone with both of its opposite charges creates a neutral molecule and through resonance it is a stable molecule. The extra electron that created t
negative charge on either terminal oxygen can be delocalized by resonance through the terminal oxygens.

Benzene is an extremely stable molecule and it is accounted for its geometry and molecular orbital interaction, but most importantly it's due to
resonance structures. The delocalized electrons in the benzene ring make the molecule very stable and with its characteristics of a nucleophile, it w
react with a strong electrophile only and after the first reactivity, the substituted benzene will depend on its resonance to direct the next position for t
reaction to add a second substituent.

The next molecule, the Amide, is a very stable molecule that is present in most biological systems, mainly in proteins. By studies of NM
spectroscopy and X-Ray crystallography it is confirmed that the stability of the amide is due to resonance which through molecular orbital interacti
creates almost a double bond between the Nitrogen and the carbon.

Example 5: Multiple Resonance of other Molecules


Molecules with more than one resonance form

Some structural resonance conformations are the major contributor or the dominant forms that the molecule exists. For example, if we look at t
above rules for estimating the stability of a molecule, we see that for the third molecule the first and second forms are the major contributors for t
overall stability of the molecule. The nitrogen is more electronegative than carbon so, it can handle the negative charge more than carbon. A carb
with a negative charge is the least favorable conformation for the molecule to exist, so the last resonance form contributes very little for the stability
the Ion.

The Hybrid Resonance forms show the different Lewis structures with the electron been delocalized. This is very important for the reactivity of chlo
benzene because in the presence of an electrophile it will react and the formation of another bond will be directed and determine by resonance. T
long pair of electrons delocalized in the aromatic substituted ring is where it can potentially form a new bond with an electrophile, as it is shown th
are three possible places that reactivity can take place, the first to react will take place at the para position with respect to the chloro substituent a
then to either ortho position.

References
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2.

Petrucci, Ralph H., et al. General Chemistry: Principles and Modern Applications. New Jersey: Pearson
Prentice Hall, 2007. Print.
Ahmad, Wan-Yaacob and Zakaria, Mat B. "Drawing Lewis Structures from Lewis Symbols: A Direct Electron
Pairing Approach." Journal of Chemical Education: Journal 77.3: n. pag. Web. March 2000. Link to this
journal:http://pkukmweb.ukm.my/~mbz/c_penerbitan/jurnal/jce2k77%283%29/p329.pdf

Outside links
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http://en.wikipedia.org/wiki/Resonance_(chemistry)
http://www.absoluteastronomy.com/topics/Resonance_(chemistry)#encyclopedia
http://www.nku.edu/~russellk/tutorial/reson/resonance.html
http://en.wikipedia.org/wiki/Formal_charge
http://commons.wikimedia.org/wiki/Main_Page (for the electronegatvity chart)
http://misterguch.brinkster.net/PRA037.pdf (for problem 5)
http://commons.wikimedia.org/wiki/File:Phosphite-ion-resonance-structures-2D.png (for the (HPO32-) problem
4 answer)
8.
http://commons.wikimedia.org/wiki/File:Sulfate-resonance-2D.png (for the Sulfate answer)
9.
http://www.mpcfaculty.net/mark_bishop/resonance.htm
10.
http://www.chem.ucla.edu/harding/tutorials/resonance/draw_res_str.html

Problems
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True or False, The picture below is a resonance structure?

Draw the Lewis Dot Structure for SO42- and all possible resonance structures. Which of the following
resonance structure is not favored among the Lewis Structures? Explain why. Assign Formal Charges.
Draw the Lewis Dot Structure for CH3COO- and all possible resonance structures. Assign Formal Charges.
Choose the most favorable Lewis Structure.
Draw the Lewis Dot Structure for HPO3 and all possible resonance structures. Assign Formal Charges.
Draw the Lewis Dot Structure for CHO21- and all possible resonance structures. Assign Formal Charges.
Draw the Resonance Hybrid Structure for PO43-.
Draw the Resonance Hybrid Structure for NO3-.
2-

Problems #2

Answers
1. False, because the electrons were not moved around, only the atoms (this violates the Resonance Structure
Rules).
2. Below are the all Lewis dot structure with formal charges (in red) for Sulfate (SO42-). There isn't a most favorable
resonance of the Sulfate ion because they are all identical in charge and there is no change in Electronegativity
between the Oxygen atoms.

3. Below is the resonance for CH3COO-, formal charges are displayed in red. The Lewis Structure with the most
formal charges is not desirable, because we want the Lewis Structure with the least formal charge.

4. The resonance for HPO32-, and the formal charges (in red).

5. The resonance for CHO21-, and the formal charges (in red).

6. The resonance hybrid for PO43-, hybrid bonds are in red.

7. The resonance hybrid for NO3-, hybrid bonds are in red.

Problems #2

Contributors

compound is a substance formed when two or more chemical elements are chemically bonded together.
Two types of chemical bonds common in compounds are covalent bonds and ionic bonds.
The elements in any compound are always present in fixed ratios.
Example 1: Pure water is a compound made from two elements - hydrogen and oxygen. The ratio of hydrogen to oxygen in water
is always 2:1. Each molecule of water contains two hydrogen atoms bonded to a single oxygen atom.
Example 2: Pure table salt is a compound made from two elements - sodium and chlorine. The ratio of sodium ions to chloride
ions in sodium chloride is always 1:1.
Example 3: Pure methane is a compound made from two elements - carbon and hydrogen. The ration of hydrogen to carbon in
methane is always 4:1.
Compounds can be decomposed chemically into their constituent elements.

What is an Element?
An element is a substance consisting of atoms which all have the same number of protons - i.e. the same atomic
number.
Elements are chemically the simplest substances and hence cannot be broken down using chemical methods.
Elements can only be changed into other elements using nuclear methods.
Although an element's atoms must all have the same number of protons, they can have different numbers of
neutrons and hence different masses. When atoms of the same element have different numbers of neutrons, they are
called isotopes.

The Most Abundant Elements


With only one proton, hydrogen is the simplest, lightest element, followed by helium, which has two protons.
At 75 percent, hydrogen is also the most abundant element in the universe, followed again by helium at 23 percent,
then oxygen at 1 percent. Each oxygen atom has eight protons. All of the other elements make up the remaining 1
percent.
In the earth's crust, oxygen (47 %) is the most abundant element, followed by silicon (28 %) and aluminum(8 %).

Element Names and Numbers

All of the elements have been named. Some of these names are familiar to us, such as nitrogen and sodium, and
some are less familiar, such as dysprosiumand roentgenium.
We can also name elements using their atomic numbers. For example, element 1 is hydrogen, element 2 is helium,
element 3 is lithium, element 8 is oxygen, etc.

How Many Elements Are There?


There are currently 115 accepted elements and three elements whose existence has been claimed, but not yet
accepted (elements 113, 115 and 118).
We use the periodic table to display all of the elements in an organized way.

Elements Ancient and Modern


Some elements have been known for thousands of years, and we do not know who discovered them. These are:
antimony, arsenic, carbon, copper, iron, gold, lead, mercury, silver, sulfur, and tin.
All other elements have been discovered since 1669; it was in this year that Hennig Brand became the first named
person to discover a new element - phosphorus.

Combining Elements
An element can combine with one or more other elements to form compounds, of which there are millions. For
example, one of the best known compounds is water, written chemically as H20, which means that water is made of
two atoms of hydrogen combined with one of oxygen.

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