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 O1-C2 with 0.9985 electrons
__has 65.98% O 1 character in a sp2.40 hybrid
__has 34.02% C 2 character in a sp2.13 hybrid
2. A bonding orbital for O1-H5 with 0.9926 electrons
__has 75.40% O 1 character in a s0.88 p3 hybrid
__has 24.60% H 5 character in a s orbital
3. A bonding orbital for C2-O3 with 0.9983 electrons
__has 35.52% C 2 character in a sp1.88 hybrid
__has 64.48% O 3 character in a sp2.23 hybrid
4. A bonding orbital for C2-O4 with 0.9989 electrons
__has 34.60% C 2 character in a sp1.98 hybrid
__has 65.40% O 4 character in a sp2.22 hybrid
9. A lone pair orbital for O1 with 0.9882 electrons
__made from a sp1.08 hybrid
10. A lone pair orbital for O1 with 0.9329 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
11. A lone pair orbital for C2 with 0.2838 electrons
__made from a p-pi orbital ( 99.97% p)
12. A lone pair orbital for O3 with 0.9916 electrons
__made from a sp0.45 hybrid
13. A lone pair orbital for O3 with 0.9673 electrons
__made from a p3 hybrid
14. A lone pair orbital for O3 with 0.8787 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)
15. A lone pair orbital for O4 with 0.9915 electrons
__made from a sp0.46 hybrid
16. A lone pair orbital for O4 with 0.9702 electrons
__made from a p3 hybrid
17. A lone pair orbital for O4 with 0.8980 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)
-With core pairs on: O 1 C 2 O 3 O 4 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9974 electrons
__has 66.17% O 1 character in a sp2.45 hybrid
__has 33.83% C 2 character in a sp2.55 hybrid
2. A bonding orbital for O1-H5 with 0.9913 electrons
__has 75.26% O 1 character in a s0.85 p3 hybrid
__has 24.74% H 5 character in a s orbital
3. A bonding orbital for C2-O3 with 0.9766 electrons
__has 40.14% C 2 character in a sp1.75 hybrid
__has 59.86% O 3 character in a sp2.26 hybrid
4. A bonding orbital for C2-O4 with 0.9664 electrons
__has 39.99% C 2 character in a sp1.81 hybrid
__has 60.01% O 4 character in a sp2.25 hybrid
5. A bonding orbital for O3-O4 with 0.8976 electrons
__has 57.18% O 3 character in a p3 hybrid
__has 42.82% O 4 character in a s0.06 p3 hybrid
10. A lone pair orbital for O1 with 0.9858 electrons
__made from a sp1.04 hybrid
11. A lone pair orbital for O1 with 0.9387 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
12. A lone pair orbital for C2 with 0.3247 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)
13. A lone pair orbital for O3 with 0.9903 electrons
__made from a sp0.46 hybrid
14. A lone pair orbital for O3 with 0.8531 electrons
__made from a p-pi orbital ( 99.87% p 0.13% d)
15. A lone pair orbital for O4 with 0.9902 electrons
__made from a sp0.48 hybrid
16. A lone pair orbital for O4 with 0.8761 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)
-With core pairs on: O 1 C 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 bonding donor orbital, 3, for C2-O3 with
the antibonding acceptor orbital, 102, for O3-O4 is 52.7 kJ/mol.
The interaction of bonding donor orbital, 4, for C2-O4 with
the antibonding acceptor orbital, 102, for O3-O4 is 100. kJ/mol.
The interaction of bonding donor orbital, 5, for O3-O4 with
the antibonding acceptor orbital, 98, for O1-C2 is 154. kJ/mol.
The interaction of bonding donor orbital, 5, for O3-O4 with
the antibonding acceptor orbital, 100, for C2-O3 is 37.8 kJ/mol.
The interaction of bonding donor orbital, 5, for O3-O4 with
the antibonding acceptor orbital, 101, for C2-O4 is 33.8 kJ/mol.
The interaction of lone pair donor orbital, 10, for O1 with
the antibonding acceptor orbital, 101, for C2-O4 is 23.2 kJ/mol.
The interaction of the second lone pair donor orbital, 11, for O1 with
the lone pair acceptor orbital, 12, for C2 is 156. kJ/mol.
The interaction of the second lone pair donor orbital, 14, for O3 with
the lone pair acceptor orbital, 12, for C2 is 442. kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O4 with
the lone pair acceptor orbital, 12, for C2 is 359. 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 ----- 3.826
19 ----- 2.554
18 ----- -0.184
17 ----- -1.406
16 -^--- -8.550
15 -^-v- -8.645
14 -^-v- -9.378
13 -^-v- -9.740
12 -^-v- -11.25
11 -^-v- -12.92
10 -^-v- -13.05
9 -^-v- -13.74
8 -^-v- -16.84
7 -^-v- -26.15
6 -^-v- -27.22
5 -^-v- -29.65
4 -^-v- -271.9
3 -^-v- -508.6
2 -^-v- -508.6
1 -^-v- -509.1
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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 = -264.4501534182 Hartrees
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