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 O1-C2 with 1.9922 electrons
__has 63.81% O 1 character in a sp2.24 hybrid
__has 36.19% C 2 character in a sp2.09 hybrid
2. A bonding orbital for O1-C2 with 1.9900 electrons
__has 76.73% O 1 character in a p3 hybrid
__has 23.27% C 2 character in a p3 hybrid
3. A bonding orbital for O1-C5 with 1.9032 electrons
__has 87.27% O 1 character in a s0.07 p3 hybrid
__has 12.73% C 5 character in a p3 hybrid
4. A bonding orbital for C2-O3 with 1.9977 electrons
__has 35.19% C 2 character in a sp2.07 hybrid
__has 64.81% O 3 character in a sp1.99 hybrid
5. A bonding orbital for C2-C5 with 1.9460 electrons
__has 50.68% C 2 character in a sp1.85 hybrid
__has 49.32% C 5 character in a sp2.34 hybrid
6. A bonding orbital for O3-H4 with 1.9805 electrons
__has 78.02% O 3 character in a s0.91 p3 hybrid
__has 21.98% H 4 character in a s orbital
7. A bonding orbital for C5-C6 with 1.9891 electrons
__has 52.47% C 5 character in a sp1.56 hybrid
__has 47.53% C 6 character in a sp2.61 hybrid
8. A bonding orbital for C5-H10 with 1.9782 electrons
__has 63.15% C 5 character in a sp2.21 hybrid
__has 36.85% H10 character in a s orbital
9. A bonding orbital for C6-H7 with 1.9631 electrons
__has 63.96% C 6 character in a s0.97 p3 hybrid
__has 36.04% H 7 character in a s orbital
10. A bonding orbital for C6-H8 with 1.9891 electrons
__has 63.03% C 6 character in a sp2.72 hybrid
__has 36.97% H 8 character in a s orbital
11. A bonding orbital for C6-H9 with 1.9217 electrons
__has 63.51% C 6 character in a s0.81 p3 hybrid
__has 36.49% H 9 character in a s orbital
17. A lone pair orbital for O1 with 1.9835 electrons
__made from a sp0.50 hybrid
18. A lone pair orbital for O3 with 1.9683 electrons
__made from a sp1.31 hybrid
19. A lone pair orbital for O3 with 1.8060 electrons
__made from a p-pi orbital ( 99.91% p 0.09% d)
141. A antibonding orbital for O1-C2 with 0.2022 electrons
__has 23.27% O 1 character in a p3 hybrid
__has 76.73% C 2 character in a p3 hybrid
142. A antibonding orbital for O1-C5 with 0.1493 electrons
__has 12.73% O 1 character in a s0.07 p3 hybrid
__has 87.27% C 5 character in a p3 hybrid
-With core pairs on: O 1 C 2 O 3 C 5 C 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 bonding donor orbital, 3, for O1-C5 with
the antibonding acceptor orbital, 140, for O1-C2 is 70.5 kJ/mol.
The interaction of bonding donor orbital, 3, for O1-C5 with
the antibonding acceptor orbital, 143, for C2-O3 is 202. kJ/mol.
The interaction of bonding donor orbital, 3, for O1-C5 with
the antibonding acceptor orbital, 144, for C2-C5 is 28.8 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C5 with
the antibonding acceptor orbital, 142, for O1-C5 is 96.8 kJ/mol.
The interaction of bonding donor orbital, 6, for O3-H4 with
the antibonding acceptor orbital, 144, for C2-C5 is 41.7 kJ/mol.
The interaction of bonding donor orbital, 8, for C5-H10 with
the second antibonding acceptor orbital, 141, for O1-C2 is 22.0 kJ/mol.
The interaction of bonding donor orbital, 9, for C6-H7 with
the antibonding acceptor orbital, 142, for O1-C5 is 42.4 kJ/mol.
The interaction of bonding donor orbital, 11, for C6-H9 with
the antibonding acceptor orbital, 142, for O1-C5 is 93.6 kJ/mol.
The interaction of lone pair donor orbital, 18, for O3 with
the antibonding acceptor orbital, 140, for O1-C2 is 62.0 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O3 with
the second antibonding acceptor orbital, 141, for O1-C2 is 381. 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.
23 ----- -3.536
22 ----- -4.991
21 ----- -8.131
20 ----- -10.04
19 -^-v- -14.15
18 -^-v- -14.70
17 -^-v- -15.29
16 -^-v- -16.11
15 -^-v- -16.40
14 -^-v- -16.71
13 -^-v- -18.19
12 -^-v- -18.63
11 -^-v- -19.44
10 -^-v- -21.85
9 -^-v- -23.35
8 -^-v- -26.16
7 -^-v- -32.97
6 -^-v- -34.78
5 -^-v- -272.6
4 -^-v- -275.5
3 -^-v- -277.0
2 -^-v- -514.2
1 -^-v- -514.8
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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 = -267.5408182482 Hartrees
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