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.
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 0.9959 electrons
__has 49.37% C 1 character in a sp2.68 hybrid
__has 50.63% C 2 character in a sp2.63 hybrid
2. A bonding orbital for C1-H3 with 0.9954 electrons
__has 59.30% C 1 character in a s0.97 p3 hybrid
__has 40.70% H 3 character in a s orbital
3. A bonding orbital for C1-H4 with 0.9958 electrons
__has 59.44% C 1 character in a s0.94 p3 hybrid
__has 40.56% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 0.9962 electrons
__has 59.77% C 1 character in a s0.98 p3 hybrid
__has 40.23% H 5 character in a s orbital
5. A bonding orbital for C2-C6 with 0.9948 electrons
__has 49.05% C 2 character in a s0.89 p3 hybrid
__has 50.95% C 6 character in a sp2.88 hybrid
6. A bonding orbital for C2-C7 with 0.9959 electrons
__has 50.63% C 2 character in a sp2.64 hybrid
__has 49.37% C 7 character in a sp2.69 hybrid
7. A bonding orbital for C2-O8 with 0.9977 electrons
__has 33.79% C 2 character in a s0.85 p3 hybrid
__has 66.21% O 8 character in a sp2.34 hybrid
8. A bonding orbital for C6-H9 with 0.9966 electrons
__has 58.95% C 6 character in a s0.92 p3 hybrid
__has 41.05% H 9 character in a s orbital
9. A bonding orbital for C6-H10 with 0.9969 electrons
__has 59.98% C 6 character in a sp2.93 hybrid
__has 40.02% H10 character in a s orbital
10. A bonding orbital for C6-H11 with 0.9969 electrons
__has 59.98% C 6 character in a sp2.93 hybrid
__has 40.02% H11 character in a s orbital
11. A bonding orbital for C7-H12 with 0.9954 electrons
__has 59.30% C 7 character in a s0.97 p3 hybrid
__has 40.70% H12 character in a s orbital
12. A bonding orbital for C7-H13 with 0.9962 electrons
__has 59.77% C 7 character in a s0.98 p3 hybrid
__has 40.23% H13 character in a s orbital
13. A bonding orbital for C7-H14 with 0.9958 electrons
__has 59.44% C 7 character in a s0.94 p3 hybrid
__has 40.56% H14 character in a s orbital
19. A lone pair orbital for O8 with 0.9947 electrons
__made from a sp0.43 hybrid
20. A lone pair orbital for O8 with 0.9851 electrons
__made from a p3 hybrid
21. A lone pair orbital for O8 with 0.9786 electrons
__made from a p-pi orbital ( 99.96% p)
-With core pairs on: C 1 C 2 C 6 C 7 O 8 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9920 electrons
__has 48.20% C 1 character in a sp2.72 hybrid
__has 51.80% C 2 character in a sp2.65 hybrid
2. A bonding orbital for C1-H3 with 0.9955 electrons
__has 59.17% C 1 character in a s0.97 p3 hybrid
__has 40.83% H 3 character in a s orbital
3. A bonding orbital for C1-H4 with 0.9962 electrons
__has 59.33% C 1 character in a s0.95 p3 hybrid
__has 40.67% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 0.9964 electrons
__has 59.64% C 1 character in a s0.98 p3 hybrid
__has 40.36% H 5 character in a s orbital
5. A bonding orbital for C2-C6 with 0.9663 electrons
__has 54.56% C 2 character in a s0.88 p3 hybrid
__has 45.44% C 6 character in a s0.96 p3 hybrid
6. A bonding orbital for C2-C7 with 0.9919 electrons
__has 51.80% C 2 character in a sp2.65 hybrid
__has 48.20% C 7 character in a sp2.73 hybrid
7. A bonding orbital for C2-O8 with 0.9973 electrons
__has 38.30% C 2 character in a s0.88 p3 hybrid
__has 61.70% O 8 character in a sp2.16 hybrid
8. A bonding orbital for C6-H9 with 0.9930 electrons
__has 59.75% C 6 character in a s0.99 p3 hybrid
__has 40.25% H 9 character in a s orbital
9. A bonding orbital for C6-H10 with 0.9971 electrons
__has 59.50% C 6 character in a sp2.93 hybrid
__has 40.50% H10 character in a s orbital
10. A bonding orbital for C6-H11 with 0.9971 electrons
__has 59.50% C 6 character in a sp2.93 hybrid
__has 40.50% H11 character in a s orbital
11. A bonding orbital for C7-H12 with 0.9955 electrons
__has 59.17% C 7 character in a s0.97 p3 hybrid
__has 40.83% H12 character in a s orbital
12. A bonding orbital for C7-H13 with 0.9964 electrons
__has 59.64% C 7 character in a s0.98 p3 hybrid
__has 40.36% H13 character in a s orbital
13. A bonding orbital for C7-H14 with 0.9962 electrons
__has 59.33% C 7 character in a s0.95 p3 hybrid
__has 40.67% H14 character in a s orbital
19. A lone pair orbital for O8 with 0.9938 electrons
__made from a sp0.46 hybrid
20. A lone pair orbital for O8 with 0.9742 electrons
__made from a p-pi orbital ( 99.97% p)
-With core pairs on: C 1 C 2 C 6 C 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, 5, for C2-C6 with
the third lone pair acceptor orbital, 21, for O8 is 49.5 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O8 with
the antibonding acceptor orbital, 162, for C1-C2 is 26.9 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O8 with
the antibonding acceptor orbital, 167, for C2-C7 is 26.8 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.
25 ----- 2.101
24 ----- 2.018
23 ----- 1.793
22 ----- 0.968
21 -^--- -6.194
20 -^-v- -6.904
19 -^-v- -8.741
18 -^-v- -8.917
17 -^-v- -9.098
16 -^-v- -9.231
15 -^-v- -9.865
14 -^-v- -10.10
13 -^-v- -11.32
12 -^-v- -11.33
11 -^-v- -11.46
10 -^-v- -13.28
9 -^-v- -17.05
8 -^-v- -17.27
7 -^-v- -19.19
6 -^-v- -25.11
5 -^-v- -266.2 4 -^-v- -266.2
3 -^-v- -266.8
2 -^-v- -268.3
1 -^-v- -507.0
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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 = -233.0788024510 Hartrees
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