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-O3 with 1.9898 electrons
__has 33.40% C 1 character in a sp2.31 hybrid
__has 66.60% O 3 character in a sp2.57 hybrid
2. A bonding orbital for C1-O4 with 1.9898 electrons
__has 33.41% C 1 character in a sp2.31 hybrid
__has 66.59% O 4 character in a sp2.58 hybrid
3. A bonding orbital for C1-O5 with 1.9929 electrons
__has 37.00% C 1 character in a sp1.51 hybrid
__has 63.00% O 5 character in a sp1.79 hybrid
4. A bonding orbital for C1-O5 with 1.9905 electrons
__has 27.84% C 1 character in a p3 hybrid
__has 72.16% O 5 character in a p3 hybrid
5. A bonding orbital for C2-O6 with 1.9929 electrons
__has 37.00% C 2 character in a sp1.50 hybrid
__has 63.00% O 6 character in a sp1.79 hybrid
6. A bonding orbital for C2-O6 with 1.9905 electrons
__has 27.84% C 2 character in a p-pi orbital ( 99.31% p 0.68% d)
__has 72.16% O 6 character in a p-pi orbital ( 99.78% p 0.22% d)
7. A bonding orbital for C2-O7 with 1.9898 electrons
__has 33.42% C 2 character in a sp2.31 hybrid
__has 66.58% O 7 character in a sp2.58 hybrid
8. A bonding orbital for C2-O8 with 1.9898 electrons
__has 33.39% C 2 character in a sp2.32 hybrid
__has 66.61% O 8 character in a sp2.57 hybrid
9. A bonding orbital for O3-O8 with 1.9695 electrons
__has 50.01% O 3 character in a s0.33 p3 hybrid
__has 49.99% O 8 character in a s0.33 p3 hybrid
10. A bonding orbital for O4-O7 with 1.9693 electrons
__has 49.99% O 4 character in a s0.33 p3 hybrid
__has 50.01% O 7 character in a s0.33 p3 hybrid
19. A lone pair orbital for O3 with 1.9796 electrons
__made from a sp0.61 hybrid
20. A lone pair orbital for O3 with 1.9027 electrons
__made from a p3 hybrid
21. A lone pair orbital for O4 with 1.9797 electrons
__made from a sp0.61 hybrid
22. A lone pair orbital for O4 with 1.9036 electrons
__made from a p3 hybrid
23. A lone pair orbital for O5 with 1.9773 electrons
__made from a sp0.55 hybrid
24. A lone pair orbital for O5 with 1.8357 electrons
__made from a p-pi orbital ( 99.86% p 0.14% d)
25. A lone pair orbital for O6 with 1.9773 electrons
__made from a sp0.55 hybrid
26. A lone pair orbital for O6 with 1.8357 electrons
__made from a p-pi orbital ( 99.86% p 0.14% d)
27. A lone pair orbital for O7 with 1.9797 electrons
__made from a sp0.61 hybrid
28. A lone pair orbital for O7 with 1.9036 electrons
__made from a p3 hybrid
29. A lone pair orbital for O8 with 1.9796 electrons
__made from a sp0.62 hybrid
30. A lone pair orbital for O8 with 1.9027 electrons
__made from a p3 hybrid
186. A antibonding orbital for C1-O5 with 0.1777 electrons
__has 72.16% C 1 character in a p3 hybrid
__has 27.84% O 5 character in a p3 hybrid
188. A antibonding orbital for C2-O6 with 0.1777 electrons
__has 72.16% C 2 character in a p-pi orbital ( 99.31% p 0.68% d)
__has 27.84% O 6 character in a p-pi orbital ( 99.78% p 0.22% d)
-With core pairs on: C 1 C 2 O 3 O 4 O 5 O 6 O 7 O 8 -
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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, 9, for O3-O8 with
the antibonding acceptor orbital, 185, for C1-O5 is 22.4 kJ/mol.
The interaction of bonding donor orbital, 9, for O3-O8 with
the antibonding acceptor orbital, 187, for C2-O6 is 22.2 kJ/mol.
The interaction of bonding donor orbital, 10, for O4-O7 with
the antibonding acceptor orbital, 185, for C1-O5 is 21.6 kJ/mol.
The interaction of bonding donor orbital, 10, for O4-O7 with
the antibonding acceptor orbital, 187, for C2-O6 is 21.7 kJ/mol.
The interaction of lone pair donor orbital, 19, for O3 with
the antibonding acceptor orbital, 184, for C1-O4 is 23.8 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O3 with
the second antibonding acceptor orbital, 186, for C1-O5 is 175. kJ/mol.
The interaction of lone pair donor orbital, 21, for O4 with
the antibonding acceptor orbital, 183, for C1-O3 is 23.7 kJ/mol.
The interaction of the second lone pair donor orbital, 22, for O4 with
the second antibonding acceptor orbital, 186, for C1-O5 is 169. kJ/mol.
The interaction of the second lone pair donor orbital, 24, for O5 with
the antibonding acceptor orbital, 183, for C1-O3 is 172. kJ/mol.
The interaction of the second lone pair donor orbital, 24, for O5 with
the antibonding acceptor orbital, 184, for C1-O4 is 172. kJ/mol.
The interaction of the second lone pair donor orbital, 26, for O6 with
the antibonding acceptor orbital, 189, for C2-O7 is 172. kJ/mol.
The interaction of the second lone pair donor orbital, 26, for O6 with
the antibonding acceptor orbital, 190, for C2-O8 is 172. kJ/mol.
The interaction of lone pair donor orbital, 27, for O7 with
the antibonding acceptor orbital, 190, for C2-O8 is 23.7 kJ/mol.
The interaction of the second lone pair donor orbital, 28, for O7 with
the second antibonding acceptor orbital, 188, for C2-O6 is 170. kJ/mol.
The interaction of lone pair donor orbital, 29, for O8 with
the antibonding acceptor orbital, 189, for C2-O7 is 23.8 kJ/mol.
The interaction of the second lone pair donor orbital, 30, for O8 with
the second antibonding acceptor orbital, 188, for C2-O6 is 174. kJ/mol.
The interaction of the second antibonding donor orbital, 186, for C1-O5 with
the antibonding acceptor orbital, 191, for O3-O8 is 26.1 kJ/mol.
The interaction of the second antibonding donor orbital, 186, for C1-O5 with
the antibonding acceptor orbital, 192, for O4-O7 is 30.8 kJ/mol.
The interaction of the second antibonding donor orbital, 188, for C2-O6 with
the antibonding acceptor orbital, 191, for O3-O8 is 26.9 kJ/mol.
The interaction of the second antibonding donor orbital, 188, for C2-O6 with
the antibonding acceptor orbital, 192, for O4-O7 is 29.7 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.
34 ----- -2.163
33 ----- -2.474
32 ----- -5.448
31 ----- -5.473
30 -^-v- -8.446
29 -^-v- -9.323
28 -^-v- -9.422
27 -^-v- -9.472
26 -^-v- -9.851
25 -^-v- -11.11
24 -^-v- -11.87
23 -^-v- -12.15
22 -^-v- -12.43
21 -^-v- -12.83
20 -^-v- -13.04
19 -^-v- -14.33
18 -^-v- -14.50
17 -^-v- -14.76
16 -^-v- -17.80
15 -^-v- -18.46
14 -^-v- -25.78
13 -^-v- -26.11
12 -^-v- -27.92
11 -^-v- -29.41
10 -^-v- -29.63
9 -^-v- -31.83
8 -^-v- -272.8 7 -^-v- -272.8
6 -^-v- -508.4 5 -^-v- -508.4
4 -^-v- -511.2 3 -^-v- -511.2 2 -^-v- -511.2 1 -^-v- -511.2
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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 = -527.6060320335 Hartrees
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