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 1.9911 electrons
__has 48.63% C 1 character in a s0.97 p3 hybrid
__has 51.37% C 2 character in a sp1.67 hybrid
2. A bonding orbital for C1-O3 with 1.9812 electrons
__has 40.89% C 1 character in a sp2.56 hybrid
__has 59.11% O 3 character in a sp2.81 hybrid
3. A bonding orbital for C1-H4 with 1.9871 electrons
__has 54.44% C 1 character in a s0.91 p3 hybrid
__has 45.56% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 1.9884 electrons
__has 55.70% C 1 character in a s0.97 p3 hybrid
__has 44.30% H 5 character in a s orbital
5. A bonding orbital for C2-H6 with 1.9884 electrons
__has 55.07% C 2 character in a sp2.38 hybrid
__has 44.93% H 6 character in a s orbital
6. A bonding orbital for C2-O7 with 1.9967 electrons
__has 34.02% C 2 character in a sp2.19 hybrid
__has 65.98% O 7 character in a sp1.74 hybrid
7. A bonding orbital for C2-O7 with 1.9940 electrons
__has 25.70% C 2 character in a s0.08 p3 hybrid
__has 74.30% O 7 character in a s0.08 p3 hybrid
12. A lone pair orbital for O3 with 1.9911 electrons
__made from a sp0.35 hybrid
13. A lone pair orbital for O3 with 1.9220 electrons
__made from a p3 hybrid
14. A lone pair orbital for O3 with 1.8802 electrons
__made from a p3 hybrid
15. A lone pair orbital for O7 with 1.9830 electrons
__made from a sp0.63 hybrid
16. A lone pair orbital for O7 with 1.9171 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 O 3 O 7 -
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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 bonding donor orbital, 2, for C1-O3 with
the second antibonding acceptor orbital, 114, for C2-O7 is 22.0 kJ/mol.
The interaction of the second lone pair donor orbital, 13, for O3 with
the antibonding acceptor orbital, 110, for C1-H4 is 74.0 kJ/mol.
The interaction of the second lone pair donor orbital, 13, for O3 with
the antibonding acceptor orbital, 111, for C1-H5 is 71.2 kJ/mol.
The interaction of the third lone pair donor orbital, 14, for O3 with
the antibonding acceptor orbital, 108, for C1-C2 is 49.7 kJ/mol.
The interaction of the third lone pair donor orbital, 14, for O3 with
the antibonding acceptor orbital, 110, for C1-H4 is 21.9 kJ/mol.
The interaction of the third lone pair donor orbital, 14, for O3 with
the second antibonding acceptor orbital, 114, for C2-O7 is 57.9 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O7 with
the antibonding acceptor orbital, 108, for C1-C2 is 85.1 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O7 with
the antibonding acceptor orbital, 112, for C2-H6 is 116. 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 ----- 7.673
19 ----- 7.397
18 ----- 6.614
17 ----- 3.668
16 -^-v- 1.030
15 -^-v- 0.771
14 -^-v- -0.624
13 -^-v- -2.961
12 -^-v- -3.721
11 -^-v- -4.284
10 -^-v- -5.163
9 -^-v- -5.931
8 -^-v- -8.327
7 -^-v- -10.78
6 -^-v- -17.24
5 -^-v- -19.88
4 -^-v- -261.7
3 -^-v- -262.9
2 -^-v- -498.6
1 -^-v- -500.6
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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 = -228.5423930142 Hartrees
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