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. (This
analysis was run at the DZVP level with diffuse functions instead
of the TZVP level, because of the size of the calculation.)
Hybridization in the Best Lewis Structure
1. A bonding orbital for O1-O2 with 1.9851 electrons
__has 50.00% O 1 character in a s0.29 p3 hybrid
__has 50.00% O 2 character in a s0.29 p3 hybrid
2. A bonding orbital for O1-C6 with 1.9884 electrons
__has 72.38% O 1 character in a sp2.42 hybrid
__has 27.62% C 6 character in a sp2.86 hybrid
3. A bonding orbital for O2-C3 with 1.9884 electrons
__has 72.38% O 2 character in a sp2.42 hybrid
__has 27.62% C 3 character in a sp2.86 hybrid
4. A bonding orbital for C3-O4 with 1.9979 electrons
__has 18.25% C 3 character in a p-pi orbital ( 99.21% p 0.79% d)
__has 81.75% O 4 character in a p-pi orbital ( 99.76% p 0.24% d)
5. A bonding orbital for C3-O4 with 1.9944 electrons
__has 34.08% C 3 character in a sp1.62 hybrid
__has 65.92% O 4 character in a sp1.79 hybrid
6. A bonding orbital for C3-O5 with 1.9893 electrons
__has 34.18% C 3 character in a sp1.73 hybrid
__has 65.82% O 5 character in a sp1.93 hybrid
7. A bonding orbital for C6-O7 with 1.9893 electrons
__has 34.18% C 6 character in a sp1.73 hybrid
__has 65.82% O 7 character in a sp1.93 hybrid
8. A bonding orbital for C6-O8 with 1.9979 electrons
__has 18.25% C 6 character in a p-pi orbital ( 99.21% p 0.79% d)
__has 81.75% O 8 character in a p-pi orbital ( 99.76% p 0.24% d)
9. A bonding orbital for C6-O8 with 1.9944 electrons
__has 34.08% C 6 character in a sp1.62 hybrid
__has 65.92% O 8 character in a sp1.79 hybrid
18. A lone pair orbital for O1 with 1.9866 electrons
__made from a sp0.61 hybrid
19. A lone pair orbital for O1 with 1.9269 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
20. A lone pair orbital for O2 with 1.9866 electrons
__made from a sp0.61 hybrid
21. A lone pair orbital for O2 with 1.9269 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
22. A lone pair orbital for O4 with 1.9803 electrons
__made from a sp0.55 hybrid
23. A lone pair orbital for O4 with 1.8949 electrons
__made from a p3 hybrid
24. A lone pair orbital for O5 with 1.9814 electrons
__made from a sp0.51 hybrid
25. A lone pair orbital for O5 with 1.8951 electrons
__made from a p3 hybrid
26. A lone pair orbital for O5 with 1.7319 electrons
__made from a p-pi orbital ( 99.79% p 0.21% d)
27. A lone pair orbital for O7 with 1.9814 electrons
__made from a sp0.51 hybrid
28. A lone pair orbital for O7 with 1.8951 electrons
__made from a p3 hybrid
29. A lone pair orbital for O7 with 1.7319 electrons
__made from a p-pi orbital ( 99.79% p 0.21% d)
30. A lone pair orbital for O8 with 1.9803 electrons
__made from a sp0.55 hybrid
31. A lone pair orbital for O8 with 1.8949 electrons
__made from a p3 hybrid
145. A antibonding orbital for O1-C6 with 0.1253 electrons
__has 27.62% O 1 character in a sp2.42 hybrid
__has 72.38% C 6 character in a sp2.86 hybrid
146. A antibonding orbital for O2-C3 with 0.1253 electrons
__has 27.62% O 2 character in a sp2.42 hybrid
__has 72.38% C 3 character in a sp2.86 hybrid
147. A antibonding orbital for C3-O4 with 0.3260 electrons
__has 81.75% C 3 character in a p-pi orbital ( 99.21% p 0.79% d)
__has 18.25% O 4 character in a p-pi orbital ( 99.76% p 0.24% d)
151. A antibonding orbital for C6-O8 with 0.3260 electrons
__has 81.75% C 6 character in a p-pi orbital ( 99.21% p 0.79% d)
__has 18.25% O 8 character in a p-pi orbital ( 99.76% p 0.24% d)
-With core pairs on: O 1 O 2 C 3 O 4 O 5 C 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 lone pair donor orbital, 18, for O1 with
the second antibonding acceptor orbital, 152, for C6-O8 is 26.2 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O1 with
the antibonding acceptor orbital, 151, for C6-O8 is 152. kJ/mol.
The interaction of lone pair donor orbital, 20, for O2 with
the second antibonding acceptor orbital, 148, for C3-O4 is 26.2 kJ/mol.
The interaction of the second lone pair donor orbital, 21, for O2 with
the antibonding acceptor orbital, 147, for C3-O4 is 152. kJ/mol.
The interaction of lone pair donor orbital, 22, for O4 with
the antibonding acceptor orbital, 149, for C3-O5 is 23.8 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O4 with
the antibonding acceptor orbital, 146, for O2-C3 is 173. kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O4 with
the antibonding acceptor orbital, 149, for C3-O5 is 86.3 kJ/mol.
The interaction of lone pair donor orbital, 24, for O5 with
the second antibonding acceptor orbital, 148, for C3-O4 is 24.8 kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O5 with
the antibonding acceptor orbital, 146, for O2-C3 is 138. kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O5 with
the second antibonding acceptor orbital, 148, for C3-O4 is 75.7 kJ/mol.
The interaction of the third lone pair donor orbital, 26, for O5 with
the antibonding acceptor orbital, 147, for C3-O4 is 572. kJ/mol.
The interaction of lone pair donor orbital, 27, for O7 with
the second antibonding acceptor orbital, 152, for C6-O8 is 24.8 kJ/mol.
The interaction of the second lone pair donor orbital, 28, for O7 with
the antibonding acceptor orbital, 145, for O1-C6 is 138. kJ/mol.
The interaction of the second lone pair donor orbital, 28, for O7 with
the second antibonding acceptor orbital, 152, for C6-O8 is 75.7 kJ/mol.
The interaction of the third lone pair donor orbital, 29, for O7 with
the antibonding acceptor orbital, 151, for C6-O8 is 572. kJ/mol.
The interaction of lone pair donor orbital, 30, for O8 with
the antibonding acceptor orbital, 150, for C6-O7 is 23.8 kJ/mol.
The interaction of the second lone pair donor orbital, 31, for O8 with
the antibonding acceptor orbital, 145, for O1-C6 is 173. kJ/mol.
The interaction of the second lone pair donor orbital, 31, for O8 with
the antibonding acceptor orbital, 150, for C6-O7 is 86.3 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.
35 ----- 11.24
34 ----- 9.323
33 ----- 9.169
32 ----- 6.369
31 -^-v- 3.045
30 -^-v- 3.014
29 -^-v- 2.839
28 -^-v- 2.259
27 -^-v- 2.189
26 -^-v- 2.048
25 -^-v- 1.758
24 -^-v- 0.778
23 -^-v- 0.337
22 -^-v- -1.494
21 -^-v- -1.556
20 -^-v- -1.618
19 -^-v- -2.222
18 -^-v- -2.343
17 -^-v- -2.521
16 -^-v- -3.597
15 -^-v- -5.231
14 -^-v- -13.26
13 -^-v- -14.94
12 -^-v- -15.00
11 -^-v- -15.90
10 -^-v- -17.45
9 -^-v- -18.47
8 -^-v- -261.0 7 -^-v- -261.0
6 -^-v- -496.6 5 -^-v- -496.6
4 -^-v- -496.7 3 -^-v- -496.7
2 -^-v- -499.0 1 -^-v- -499.0
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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 = -527.7492197954 Hartrees
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