Best Lewis Structure
The Lewis structure that is closest to your structure is determined.
The hybridization of the atoms in this idealized Lewis structure
is given in the table below.
Please note that your structure can't be well described by a single
Lewis structure, because of extensive delocalization.
Hybridization in the Best Lewis Structure
1. A bonding orbital for C1-C2 with 1.9793 electrons
__has 50.00% C 1 character in a sp1.88 hybrid
__has 50.00% C 2 character in a sp1.88 hybrid
2. A bonding orbital for C1-Cl3 with 1.9836 electrons
__has 45.34% C 1 character in a sp2.47 hybrid
__has 54.66% Cl 3 character in a s0.47 p3 hybrid
3. A bonding orbital for C1-O4 with 1.9983 electrons
__has 34.66% C 1 character in a sp1.69 hybrid
__has 65.34% O 4 character in a sp1.34 hybrid
4. A bonding orbital for C1-O4 with 1.9862 electrons
__has 33.82% C 1 character in a p-pi orbital ( 99.50% p 0.50% d)
__has 66.18% O 4 character in a p-pi orbital ( 99.76% p 0.24% d)
5. A bonding orbital for C2-Cl5 with 1.9836 electrons
__has 45.34% C 2 character in a sp2.47 hybrid
__has 54.66% Cl 5 character in a s0.47 p3 hybrid
6. A bonding orbital for C2-O6 with 1.9983 electrons
__has 34.66% C 2 character in a sp1.69 hybrid
__has 65.34% O 6 character in a sp1.34 hybrid
7. A bonding orbital for C2-O6 with 1.9862 electrons
__has 33.82% C 2 character in a p-pi orbital ( 99.50% p 0.50% d)
__has 66.18% O 6 character in a p-pi orbital ( 99.76% p 0.24% d)
22. A lone pair orbital for Cl3 with 1.9941 electrons
__made from a sp0.15 hybrid
23. A lone pair orbital for Cl3 with 1.9715 electrons
__made from a p3 hybrid
24. A lone pair orbital for Cl3 with 1.9194 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)
25. A lone pair orbital for O4 with 1.9783 electrons
__made from a sp0.74 hybrid
26. A lone pair orbital for O4 with 1.8468 electrons
__made from a p3 hybrid
27. A lone pair orbital for Cl5 with 1.9941 electrons
__made from a sp0.15 hybrid
28. A lone pair orbital for Cl5 with 1.9715 electrons
__made from a p3 hybrid
29. A lone pair orbital for Cl5 with 1.9194 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)
30. A lone pair orbital for O6 with 1.9783 electrons
__made from a sp0.74 hybrid
31. A lone pair orbital for O6 with 1.8469 electrons
__made from a p3 hybrid
152. A antibonding orbital for C1-C2 with 0.1366 electrons
__has 50.00% C 1 character in a sp1.88 hybrid
__has 50.00% C 2 character in a sp1.88 hybrid
153. A antibonding orbital for C1-Cl3 with 0.1115 electrons
__has 54.66% C 1 character in a sp2.47 hybrid
__has 45.34% Cl 3 character in a s0.47 p3 hybrid
156. A antibonding orbital for C2-Cl5 with 0.1115 electrons
__has 54.66% C 2 character in a sp2.47 hybrid
__has 45.34% Cl 5 character in a s0.47 p3 hybrid
-With core pairs on: C 1 C 2 Cl 3 Cl 3 Cl 3 Cl 3 Cl 3 O 4 Cl 5 Cl 5 Cl 5 Cl 5 Cl 5 O 6 -
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Donor Acceptor Interactions in the Best Lewis Structure
The localized orbitals in your best Lewis structure
can interact strongly. A filled bonding or lone pair orbital can
act as a donor and an empty or filled bonding, antibonding, or
lone pair orbital can act as an acceptor. These
interactions can strengthen and weaken bonds. For example, a
lone pair donor->antibonding acceptor orbital interaction
will weaken the bond
associated with the antibonding orbital. Conversly, an interaction
with a bonding pair as the acceptor will strengthen the bond.
Strong electron delocalization in your best Lewis structure will
also show up as donor-acceptor interactions.
Interactions greater than 20 kJ/mol for bonding and lone pair
orbitals are listed below.
The interaction of the second bonding donor orbital, 4, for C1-O4 with
the second antibonding acceptor orbital, 158, for C2-O6 is 24.3 kJ/mol.
The interaction of the second bonding donor orbital, 7, for C2-O6 with
the second antibonding acceptor orbital, 155, for C1-O4 is 24.3 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for Cl3 with
the antibonding acceptor orbital, 152, for C1-C2 is 23.6 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for Cl3 with
the antibonding acceptor orbital, 154, for C1-O4 is 30.0 kJ/mol.
The interaction of the third lone pair donor orbital, 24, for Cl3 with
the second antibonding acceptor orbital, 155, for C1-O4 is 116. kJ/mol.
The interaction of the second lone pair donor orbital, 26, for O4 with
the antibonding acceptor orbital, 152, for C1-C2 is 142. kJ/mol.
The interaction of the second lone pair donor orbital, 26, for O4 with
the antibonding acceptor orbital, 153, for C1-Cl3 is 205. kJ/mol.
The interaction of the second lone pair donor orbital, 28, for Cl5 with
the antibonding acceptor orbital, 152, for C1-C2 is 23.6 kJ/mol.
The interaction of the second lone pair donor orbital, 28, for Cl5 with
the antibonding acceptor orbital, 157, for C2-O6 is 30.0 kJ/mol.
The interaction of the third lone pair donor orbital, 29, for Cl5 with
the second antibonding acceptor orbital, 158, for C2-O6 is 116. kJ/mol.
The interaction of the second lone pair donor orbital, 31, for O6 with
the antibonding acceptor orbital, 152, for C1-C2 is 142. kJ/mol.
The interaction of the second lone pair donor orbital, 31, for O6 with
the antibonding acceptor orbital, 156, for C2-Cl5 is 205. kJ/mol.
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Molecular Orbital Energies
The orbital energies are given in eV, where 1 eV=96.49 kJ/mol.
Orbitals with very low energy are core 1s orbitals.
More antibonding orbitals than you might expect are sometimes
listed, because d orbitals are always included for heavy
atoms and p orbitals are included for H atoms.
Up spins are shown with a ^ and down spins are shown as v.
35 ----- -0.384
34 ----- -1.772
33 ----- -2.135
32 ----- -4.976
31 -^-v- -7.750
30 -^-v- -8.614
29 -^-v- -8.880
28 -^-v- -8.897
27 -^-v- -9.071
26 -^-v- -9.328
25 -^-v- -11.44
24 -^-v- -12.16
23 -^-v- -12.83
22 -^-v- -12.92
21 -^-v- -13.36
20 -^-v- -14.31
19 -^-v- -17.80
18 -^-v- -22.27
17 -^-v- -22.29
16 -^-v- -28.20
15 -^-v- -28.54
14 -^-v- -191.3 13 -^-v- -191.3
12 -^-v- -191.4 11 -^-v- -191.4
10 -^-v- -191.8 9 -^-v- -191.8
8 -^-v- -249.8 7 -^-v- -249.8
6 -^-v- -271.6 5 -^-v- -271.6
4 -^-v- -508.5 3 -^-v- -508.5
2 -^-v- -2731. 1 -^-v- -2731.
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Total Electronic Energy
The total electronic energy is a very large number, so by convention
the units are given in atomic units, that is Hartrees (H). One
Hartree is 2625.5 kJ/mol. The energy reference is for totally
dissociated atoms. In other words, the reference state is a gas
consisting of nuclei and electrons all at infinite distance from
each other. The electronic energy includes all electric
interactions and the kinetic energy of the electrons. This energy
does not include translation, rotation, or vibration of the
the molecule.
Total electronic energy = -1147.2257622110 Hartrees
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