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-O2 with 1.9976 electrons
__has 35.40% C 1 character in a sp1.99 hybrid
__has 64.60% O 2 character in a sp2.24 hybrid
2. A bonding orbital for C1-O3 with 1.9976 electrons
__has 35.40% C 1 character in a sp1.99 hybrid
__has 64.60% O 3 character in a sp2.24 hybrid
3. A bonding orbital for C1-O3 with 1.9981 electrons
__has 12.94% C 1 character in a p-pi orbital ( 99.08% p 0.92% d)
__has 87.06% O 3 character in a p-pi orbital ( 99.93% p)
4. A bonding orbital for C1-O4 with 1.9976 electrons
__has 35.40% C 1 character in a sp1.99 hybrid
__has 64.60% O 4 character in a sp2.24 hybrid
9. A lone pair orbital for O2 with 1.9782 electrons
__made from a s orbital
10. A lone pair orbital for O2 with 1.9401 electrons
__made from a p-pi orbital ( 99.96% p)
11. A lone pair orbital for O2 with 1.7915 electrons
__made from a p-pi orbital ( 99.94% p)
12. A lone pair orbital for O3 with 1.9782 electrons
__made from a s orbital
13. A lone pair orbital for O3 with 1.9400 electrons
__made from a p-pi orbital ( 99.96% p)
14. A lone pair orbital for O4 with 1.9782 electrons
__made from a s orbital
15. A lone pair orbital for O4 with 1.9400 electrons
__made from a p-pi orbital ( 99.96% p)
16. A lone pair orbital for O4 with 1.7914 electrons
__made from a p-pi orbital ( 99.94% p)
95. A antibonding orbital for C1-O3 with 0.4000 electrons
__has 87.06% C 1 character in a p-pi orbital ( 99.08% p 0.92% d)
__has 12.94% O 3 character in a p-pi orbital ( 99.93% p)
-With core pairs on: C 1 O 2 O 3 O 4 -
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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 lone pair donor orbital, 10, for O2 with
the antibonding acceptor orbital, 94, for C1-O3 is 82.0 kJ/mol.
The interaction of the second lone pair donor orbital, 10, for O2 with
the antibonding acceptor orbital, 96, for C1-O4 is 82.0 kJ/mol.
The interaction of the third lone pair donor orbital, 11, for O2 with
the second antibonding acceptor orbital, 95, for C1-O3 is 430. kJ/mol.
The interaction of the second lone pair donor orbital, 13, for O3 with
the antibonding acceptor orbital, 93, for C1-O2 is 82.0 kJ/mol.
The interaction of the second lone pair donor orbital, 13, for O3 with
the antibonding acceptor orbital, 96, for C1-O4 is 82.0 kJ/mol.
The interaction of the second lone pair donor orbital, 15, for O4 with
the antibonding acceptor orbital, 93, for C1-O2 is 82.0 kJ/mol.
The interaction of the second lone pair donor orbital, 15, for O4 with
the antibonding acceptor orbital, 94, for C1-O3 is 82.0 kJ/mol.
The interaction of the third lone pair donor orbital, 16, for O4 with
the second antibonding acceptor orbital, 95, for C1-O3 is 431. 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.
20 ----- 15.14
19 ----- 14.90
18 ----- 14.51
17 ----- 12.90
16 -^-v- 7.660
15 -^-v- 6.166 14 -^-v- 6.165
13 -^-v- 5.927 12 -^-v- 5.926
11 -^-v- 2.262
10 -^-v- 2.161 9 -^-v- 2.160
8 -^-v- 0.479
7 -^-v- -10.11 6 -^-v- -10.11
5 -^-v- -13.11
4 -^-v- -257.0
3 -^-v- -492.6 2 -^-v- -492.6 1 -^-v- -492.6
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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 = -263.7810061477 Hartrees
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