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FORMAL CHARGE (FC)

Tool/Model for comparing which Lewis structures is more acceptable

Lewis structure SO2

Lewis structure SO3

Which is
acceptable?

Formal charge
concept

Formal Charge
Treats covalent bond with equal electron distribution no EN diff bet atom
Electronegative atom has negative while least electronegative atom
has positive formal charge.
Click here video formal charges

Click here video formal charges

Formula formal charge

L+
V - valence electrons of atom
L Lone pair electron
B - electrons shared in covalent bonds in the molecule

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge carbon dioxide

formal charge for O


L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

formal charge for C

formal charge for O

L+

L+

V- Valence electron C = 4
L - Lone pair electron C = 0
B - Bonding electron C = 8

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 4 (0+4) = 0

FC = 6 (4+2) = 0

Lowest formal charge is preferred

Formal charge carbon dioxide

Formal charge for O

Formal charge for O

Formal charge for C

L+

L+

L+

V- Valence electron C = 4
L - Lone pair electron C = 0
B - Bonding electron C = 8

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 4 (0+4) = 0

FC = 6 (4+2) = 0

Which is
acceptable?

Lowest formal charge is preferred

Different Lewis structures for CO2


Click here video CO2

-1

+1

-1

+2

-1

Lowest formal charge is preferred

Lowest formal charge more stable - contribute more to diff resonance structures.
Sum of formal charges must be zero for neutral or equal to charge on ion.

+2

-2

Formal charge dinitrogen oxide

Formal charge for N

Formal charge for O

Formal charge for N

L+

L+

L+

V- Valence electron N = 5
L- Lone pair electron N = 0
B- Bonding electron N = 8

V- Valence electron N = 5
L- Lone pair electron N = 2
B- Bonding electron N = 6

FC = 5 (2+3) = 0

V- Valence electron O = 6
L- Lone pair electron O = 6
B- Bonding electron O = 2

FC = 5 (0+4) = +1

FC = 6 (6+1) = -1

Which is acceptable?

Lowest formal charge is preferred

+1

-1

Different Lewis structures for N2O


Click here to view video

-1

+1

-2

Lowest formal charge is preferred

+1

+1

+1

-1

-1

+2

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

-1

-2

+2

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures carbonate ion

Carbonate Ion

CO 32
C

resonance structure 1

resonance structure 2

charge 2- delocalized into 2/3lower charge more stable

Resonance hybrid

Click here on video carbonate

resonance structure 3

All bonds CO32- are identical in length and strength


Hybrid of 3 resonance structures
Negative charge equally distributed over all oxygen
No O-O (single) or O=O (double) bonds found
Only O ----- O bond
Intermediate in character bet single and double bond

Bond Order =

11

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge carbonate ion

formal charge for O

formal charge for C

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 6
B- Bonding electron O = 2

L+

V- Valence electron C = 4
L - Lone pair electron C = 0
B - Bonding electron C = 8

FC = 6 (6 +1) = -1

formal charge for O

FC = 4 (0+4) = 0

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

-1
-1

0
0

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures nitrate ion

NO 3

Nitrate Ion

resonance structure 1

charge of -1 delocalized into 1/3lower charge more stable

resonance structure 2

1/3
1/3

1/3

resonance hybrid

Click here to view video

resonance structure 3

All bonds NO3- are identical in length and strength


Hybrid of 3 resonance structures
Negative charge equally distributed over all oxygen
No N-O (single) or N=O (double) bonds found
Only N ----- O bond
Intermediate in character bet single and double bond

1
Bond Order = 1 3

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge nitrate ion

formal charge for O

formal charge for N

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 6
B- Bonding electron O = 2

L+

V- Valence electron N = 5
L - Lone pair electron N = 0
B - Bonding electron N = 8

FC = 6 (6 +1) = -1

formal charge for O

FC = 5 (0+4) = +1

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

0
-1

+1

-1

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures nitrite ion

Nitrite Ion

resonance structure 1

NO 2

resonance structure 2

charge of -1 delocalized into 1/2lower charge more stable

resonance hybrid

Click here video nitrite

All bonds NO2- are identical in length and strength


Hybrid of 2 resonance structures
Negative charge equally distributed over all oxygen
NO N-O (single) or N=O (double) bonds found
Only N ----- O bond
Intermediate in character bet single and double bond

1
Bond Order = 1 2

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge nitrite ion

formal charge for O

formal charge for N

L+

L+

formal charge for O


L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

V- Valence electron N = 5
L - Lone pair electron N = 2
B - Bonding electron N = 6

V- Valence electron O = 6
L- Lone pair electron O = 6
B- Bonding electron O = 2

FC = 6 (4 +2) = 0

FC = 5 (2+3) = 0

FC = 6 (6+1) = -1

-1

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable

Resonance structures sulfur dioxide

Sulfur Dioxide

SO 2

resonance structure 1

resonance structure 2

resonance structure 3

How about structure 3?

resonance hybrid

Click here to view

All SO2 bonds are identical in length and strength


Hybrid of 2 resonance structures
Negative charge equally distributed over all oxygen
NO S-O (single) or S=O (double) bonds found
Only S ----- O bond
Intermediate in character bet single and double bond

1
Bond Order = 1 2

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge sulfur dioxide

formal charge for O

formal charge for S

L+

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

V- Valence electron S = 6
L - Lone pair electron S = 2
B - Bonding electron S = 8

FC = 6 (4 +2) = 0

FC = 6 (2+4) = 0

formal charge for O

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge, contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

Formal charge Sulfur dioxide

Formal charge for O

Formal charge for O

Formal charge for S


L+

L+

L+

V- Valence electron S = 6
L - Lone pair electron S = 2
B - Bonding electron S = 8

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4 +2) = 0

FC = 6 (2+4) = 0

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

Which is acceptable?

0
Lowest formal charge is preferred

Different Lewis structures for SO2


Click here to view

0
0

Lowest formal charge is preferred

+1
-1

+1

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable) contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

-1

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structure cyanate

Cyanate ion

NCO Which structure is


acceptable ?

resonance structure 1

resonance structure 2

-1

Contribute less

resonance structure 3

-1

+1

Lowest formal charge is preferred

Negative formal charge on


less electronegative N atom

-2

Contribute the least

High formal charge/unstable

-1

Negative formal charge located on more electronegative O atom is


more stable than one located on a less electronegative N atom

Contribute the MOST

Click here to view

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable

Xenon trioxide

XeO 3

Click here to view

Different resonance structure for XeO3

Which structure is
acceptable ?

Lowest formal charge is preferred

formal charge for O

formal charge for Xe

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

V- Valence electron Xe = 8
L- Lone pair electron Xe = 2
B- Bonding electron Xe = 12

FC = 6 (4 +2) = 0

0
0

FC = 8 (2 +6) = 0

formal charge for O


L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4 +2) = 0

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures sulfur trioxide

SO 3

Sulfur Trioxide

resonance structure 1

resonance structure 2

resonance structure 3

resonance structure 4

How about structure 4 ?

S
resonance hybrid

Click here to view video

120

All SO3 bonds are identical in length and strength


Hybrid of 3 resonance structures
NO S-O (single) or S=O (double) bonds found
Only S ----- O bond
Intermediate in character bet single and double bond

1
Bond Order = 1 3

Formal charge Sulfur Trioxide

Formal charge for O

Formal charge for O

Formal charge for S

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

V- Valence electron S = 6
L - Lone pair electron S = 0
B - Bonding electron S = 12

FC = 6 (4 +2) = 0

FC = 6 (0+6) = 0

Which is acceptable?

0
Lowest formal charge is preferred

FC = 6 (4+2) = 0

Different Lewis structures for SO3

-1

-1

0
+2

+2

+2

Lowest formal charge is preferred

-1

-1

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

-1

-1

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures methanoate

Methanoate ion

HCOO

Resonance structures ethanoate

Ethanoate ion

CH3COO

resonance structure 1

resonance structure 2

resonance structure 1

resonance structure 2

CH3

resonance hybrid

resonance hybrid

Click here to view

All CO bonds are identical in length and strength


Hybrid of 2 resonance structures
NO C-O (single) or C=O (double) bonds found
Only C ----- O bond
Intermediate character bet single and double bond

1
Bond Order = 1 2
Click here to view

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge methanoate ion

formal charge for O

formal charge for C

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 6
B- Bonding electron O = 2

V- Valence electron C = 4
L - Lone pair electron C = 0
B - Bonding electron C = 8

FC = 6 (6 +1) = -1

FC = 4 (0+4) = 0

formal charge for O


L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

FC = 6 (4+2) = 0

-1

0
0

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

Delocalization of electrons
Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures thiocyanate

Thiocyanate ion

SCN
Which is acceptable
structure?

resonance structure 1

resonance structure 2

-1

Contribute the less

resonance structure 3

-1

+1

Lowest formal charge is preferred

Negative formal charge on


less electronegative S atom

-2

Contribute the least

High formal charge/unstable

-1

Negative formal charge located on more electronegative N atom is


more stable than one located on a less electronegative S atom

Contribute the MOST

Click here to view video

Formal charge thiocyanate ion

Formal charge for S

Formal charge for C

L+

Formal charge for N

L+

V- Valence electron C = 4
L- Lone pair electron C = 0
B- Bonding electron C = 8

V- Valence electron S = 6
L- Lone pair electron S = 4
B- Bonding electron S = 4

FC = 6 (4+2) = 0

FC = 4 (0+4) = 0

L+

V- Valence electron N = 5
L- Lone pair electron N = 4
B- Bonding electron N = 4

FC = 5 (4+2) = -1

Which is acceptable?

Lowest formal charge is preferred

-1

Different Lewis structures for SCNClick here to view video

-1

Lowest formal charge is preferred

-1

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

+1

-2

Delocalization of electrons

UV radiation

Resonance
Describing delocalization of electrons within a molecule/polyatomic ion
where bonding cannot be express by ONE single Lewis structure
Delocalization of bond electrons spread over more than 2 nuclei
electrons are shared
electrons spread more stable
Resonance structures ozone
strongest radiation

Ozone

resonance structure 1

O3

resonance structure 2

Ozone at stratosphere

resonance hybrid

O3

Click here on video ozone

Pale blue gas, polar, dimagnetic


Oxidizing agent
Potent respiratory hazard and pollutant at ground level
Beneficial prevent UV B/C from reaching Earth surface
Highest ozone level in stratosphere,(10 km and 50 km)

All bonds O-O are identical in length and strength


Hybrid of 2 resonance structures
NO O-O (single) or O=O (double) bonds found
Only O ----- O bond
Intermediate in character bet single and double bond

1
Bond Order = 1 2

FORMAL CHARGE (FC)

Formal Charge
Tool/Model for comparing which Lewis structures is more acceptable
Treats covalent bond with equal electron distribution no electronegativity differences bet atom
Electronegative atom has negative while least electronegative atom has positive formal charge

Formula formal charge

L+

V - valence electrons of atom


L lone pair electron
B bonding electron molecule

Formal charge sulfur dioxide

formal charge for O

formal charge for O

L+

L+

V- Valence electron O = 6
L- Lone pair electron O = 4
B- Bonding electron O = 4

V- Valence electron O = 6
L - Lone pair electron O = 2
B - Bonding electron O = 6

FC = 6 (4 +2) = 0

FC = 6 (2+3) = +1

+1
0

-1

formal charge for O


L+

V- Valence electron O = 6
L- Lone pair electron O = 6
B- Bonding electron O = 2

FC = 6 (6+1) = -1

All resonance structure contribute to electronic structure.


Real structure is combination of them.
Lowest formal charge (stable), contribute more than less stable structure.
Sum of formal charges must be zero for neutral or equal to charge on ion.

Good Side

Ozone Good and Bad

Ozone in Strastophere
blocks UV B + C

Bad Side

Ozone in Troposphere act as


Greenhouse gas

Ozone in ground level act as


Pollutant
Photochemical

Ozone depletion

UV Exposure

Why ozone able to absorb UV B and UV C?

Click here on ozone depletion


chemicals (phaseout)

Breakdown of ozone High UV radiation


Skin cancer
- DNA mutation

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