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2d_aromaticity_post

2d_aromaticity_post

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Published by: api-3767370 on Oct 16, 2008
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05/09/2014

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Sec. 5 - Physical Properties
1
Aromaticity
Benzene
C6H6
hypothetical potential
energy if the double
bonds were isolated
Benzene is much more stable than would be expected based on
calculations for \u201ccyclohexatriene\u201d, isolated double bonds.
far more stable
than calculated
longshort
cyclohexatriene

Theoretical; 3 x -120 =-360 kJ/mol
Observed = -208 kJ/mol
Dif = 152 kJ/mol

Theoretical; 2 x -120 =-240 kJ/mol
Observed = -232 kJ/mol
Dif = 8 kJ/mol

Sec. 5 - Physical Properties
2
Molecular Orbitals (MOs) of Benzene
6 atomic p orbitals will combine to form 6 molecular orbitals
one
node
two
nodes
three
nodes
Two molecular orbitals that have the same
potential energy are called degenerate
Antibonding
Orbitals
Bonding
Orbitals
PotentialEn
ergy
\u03c01
\u03c03
\u03c02
\u03c04\u2217
\u03c06\u2217
\u03c05\u2217
Sec. 5 - Physical Properties
3
all bonding
bonding
nonbonding
antibonding
bonding
\u03c01
\u03c03
\u03c02

Four bonding interactions
and two antibonding
interactions for a net of
two bonding interactions

Two bonding interactions
and four nonbonding
interactions for a net of
two bonding interactions

Closer look at Benzene\u2019s MOs

Although you can not use the
number of bonding and
antibonding orbitals to
quantify the energy of the MO
you can see that\u03c02 and\u03c03 are

bonding MOs but not as strong
as\u03c01

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