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.
The Lewis structure is built for the up and down electrons,
separately. Note that the up and down structures can be very
different.
Hybridization in the Best Lewis Structure
Down Electrons
1. A bonding orbital for C1-C2 with 0.9975 electrons
__has 48.09% C 1 character in a sp1.93 hybrid
__has 51.91% C 2 character in a sp1.74 hybrid
2. A bonding orbital for C1-O5 with 0.9988 electrons
__has 33.91% C 1 character in a sp2.14 hybrid
__has 66.09% O 5 character in a sp1.61 hybrid
3. A bonding orbital for C1-C6 with 0.9968 electrons
__has 48.27% C 1 character in a sp1.91 hybrid
__has 51.73% C 6 character in a sp2.65 hybrid
4. A bonding orbital for C2-H3 with 0.9951 electrons
__has 61.36% C 2 character in a sp2.14 hybrid
__has 38.64% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9951 electrons
__has 60.61% C 2 character in a sp2.13 hybrid
__has 39.39% H 4 character in a s orbital
6. A bonding orbital for C6-H7 with 0.9960 electrons
__has 60.80% C 6 character in a s0.99 p3 hybrid
__has 39.20% H 7 character in a s orbital
7. A bonding orbital for C6-H8 with 0.9918 electrons
__has 60.31% C 6 character in a s0.95 p3 hybrid
__has 39.69% H 8 character in a s orbital
8. A bonding orbital for C6-H9 with 0.9898 electrons
__has 60.57% C 6 character in a s0.93 p3 hybrid
__has 39.43% H 9 character in a s orbital
13. A lone pair orbital for C1 with 0.2357 electrons
__made from a p-pi orbital ( 99.90% p 0.10% d)
14. A lone pair orbital for C2 with 0.8750 electrons
__made from a p3 hybrid
15. A lone pair orbital for O5 with 0.9912 electrons
__made from a sp0.61 hybrid
16. A lone pair orbital for O5 with 0.9657 electrons
__made from a p-pi orbital ( 99.93% p 0.06% d)
17. A lone pair orbital for O5 with 0.8997 electrons
__made from a p-pi orbital ( 99.90% p 0.10% d)
-With core pairs on: C 1 C 2 O 5 C 6 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9970 electrons
__has 53.42% C 1 character in a sp1.83 hybrid
__has 46.58% C 2 character in a sp1.80 hybrid
2. A bonding orbital for C1-O5 with 0.9985 electrons
__has 37.61% C 1 character in a sp2.18 hybrid
__has 62.39% O 5 character in a sp1.58 hybrid
3. A bonding orbital for C1-O5 with 0.9427 electrons
__has 62.53% C 1 character in a p-pi orbital ( 99.81% p 0.19% d)
__has 37.47% O 5 character in a p-pi orbital ( 99.76% p 0.24% d)
4. A bonding orbital for C1-C6 with 0.9965 electrons
__has 50.30% C 1 character in a sp1.97 hybrid
__has 49.70% C 6 character in a sp2.70 hybrid
5. A bonding orbital for C2-H3 with 0.9959 electrons
__has 56.69% C 2 character in a sp2.10 hybrid
__has 43.31% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9959 electrons
__has 55.85% C 2 character in a sp2.10 hybrid
__has 44.15% H 4 character in a s orbital
7. A bonding orbital for C6-H7 with 0.9965 electrons
__has 60.49% C 6 character in a sp2.99 hybrid
__has 39.51% H 7 character in a s orbital
8. A bonding orbital for C6-H8 with 0.9941 electrons
__has 59.27% C 6 character in a s0.96 p3 hybrid
__has 40.73% H 8 character in a s orbital
9. A bonding orbital for C6-H9 with 0.9934 electrons
__has 59.29% C 6 character in a s0.94 p3 hybrid
__has 40.71% H 9 character in a s orbital
15. A lone pair orbital for O5 with 0.9902 electrons
__made from a sp0.62 hybrid
16. A lone pair orbital for O5 with 0.9635 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 O 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 the second bonding donor orbital, 3, for C1-O5 with
the lone pair acceptor orbital, 14, for C2 is 94.6 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O5 with
the antibonding acceptor orbital, 118, for C1-C2 is 41.7 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O5 with
the antibonding acceptor orbital, 121, for C1-C6 is 50.8 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.
Only the spin up electron orbital energies are given.
20 ----- 2.238
19 ----- 1.815
18 ----- 1.544
17 ----- -1.227
16 -^--- -6.048
15 -^-v- -6.315
14 -^-v- -9.164
13 -^-v- -9.535
12 -^-v- -9.837
11 -^-v- -11.06
10 -^-v- -11.35
9 -^-v- -11.79
8 -^-v- -13.34
7 -^-v- -17.50
6 -^-v- -19.17
5 -^-v- -25.68
4 -^-v- -266.5
3 -^-v- -267.6
2 -^-v- -268.7
1 -^-v- -506.3
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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 = -192.5611869911 Hartrees
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