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 0.9967 electrons
__has 67.49% O 1 character in a sp2.32 hybrid
__has 32.51% C 2 character in a sp2.47 hybrid
2. A bonding orbital for O1-C7 with 0.9954 electrons
__has 68.19% O 1 character in a sp2.42 hybrid
__has 31.81% C 7 character in a s0.85 p3 hybrid
3. A bonding orbital for C2-O3 with 0.9981 electrons
__has 34.86% C 2 character in a sp1.90 hybrid
__has 65.14% O 3 character in a sp1.68 hybrid
4. A bonding orbital for C2-C4 with 0.9974 electrons
__has 48.23% C 2 character in a sp1.70 hybrid
__has 51.77% C 4 character in a sp1.90 hybrid
5. A bonding orbital for C4-H5 with 0.9946 electrons
__has 61.13% C 4 character in a sp2.02 hybrid
__has 38.87% H 5 character in a s orbital
6. A bonding orbital for C4-H6 with 0.9945 electrons
__has 61.91% C 4 character in a sp2.07 hybrid
__has 38.09% H 6 character in a s orbital
7. A bonding orbital for C7-H8 with 0.9966 electrons
__has 59.44% C 7 character in a sp2.86 hybrid
__has 40.56% H 8 character in a s orbital
8. A bonding orbital for C7-H9 with 0.9977 electrons
__has 58.29% C 7 character in a sp2.83 hybrid
__has 41.71% H 9 character in a s orbital
9. A bonding orbital for C7-H10 with 0.9977 electrons
__has 58.18% C 7 character in a sp2.83 hybrid
__has 41.82% H10 character in a s orbital
15. A lone pair orbital for O1 with 0.9837 electrons
__made from a sp1.44 hybrid
16. A lone pair orbital for O1 with 0.9276 electrons
__made from a p-pi orbital ( 99.95% p)
17. A lone pair orbital for C2 with 0.2696 electrons
__made from a p-pi orbital ( 99.98% p)
18. A lone pair orbital for O3 with 0.9909 electrons
__made from a sp0.59 hybrid
19. A lone pair orbital for O3 with 0.9519 electrons
__made from a p-pi orbital ( 99.91% p 0.09% d)
20. A lone pair orbital for O3 with 0.8890 electrons
__made from a p3 hybrid
21. A lone pair orbital for C4 with 0.8975 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 O 3 C 4 C 7 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9966 electrons
__has 66.99% O 1 character in a sp2.38 hybrid
__has 33.01% C 2 character in a sp2.63 hybrid
2. A bonding orbital for O1-C7 with 0.9954 electrons
__has 68.40% O 1 character in a sp2.42 hybrid
__has 31.60% C 7 character in a s0.85 p3 hybrid
3. A bonding orbital for C2-O3 with 0.9980 electrons
__has 37.82% C 2 character in a sp1.92 hybrid
__has 62.18% O 3 character in a sp1.64 hybrid
4. A bonding orbital for C2-O3 with 0.9549 electrons
__has 53.31% C 2 character in a p3 hybrid
__has 46.69% O 3 character in a p3 hybrid
5. A bonding orbital for C2-C4 with 0.9972 electrons
__has 53.34% C 2 character in a sp1.59 hybrid
__has 46.66% C 4 character in a sp1.94 hybrid
6. A bonding orbital for C4-H5 with 0.9957 electrons
__has 56.15% C 4 character in a sp2.00 hybrid
__has 43.85% H 5 character in a s orbital
7. A bonding orbital for C4-H6 with 0.9952 electrons
__has 57.07% C 4 character in a sp2.05 hybrid
__has 42.93% H 6 character in a s orbital
8. A bonding orbital for C7-H8 with 0.9965 electrons
__has 59.43% C 7 character in a sp2.85 hybrid
__has 40.57% H 8 character in a s orbital
9. A bonding orbital for C7-H9 with 0.9975 electrons
__has 58.11% C 7 character in a sp2.83 hybrid
__has 41.89% H 9 character in a s orbital
10. A bonding orbital for C7-H10 with 0.9979 electrons
__has 58.05% C 7 character in a sp2.83 hybrid
__has 41.95% H10 character in a s orbital
16. A lone pair orbital for O1 with 0.9847 electrons
__made from a sp1.41 hybrid
17. A lone pair orbital for O1 with 0.9535 electrons
__made from a p3 hybrid
18. A lone pair orbital for O3 with 0.9902 electrons
__made from a sp0.60 hybrid
19. A lone pair orbital for O3 with 0.9461 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 O 3 C 4 C 7 -
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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, 4, for C2-O3 with
the lone pair acceptor orbital, 20, for C4 is 75.9 kJ/mol.
The interaction of the second lone pair donor orbital, 17, for O1 with
the second antibonding acceptor orbital, 144, for C2-O3 is 65.7 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O3 with
the antibonding acceptor orbital, 141, for O1-C2 is 82.4 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O3 with
the antibonding acceptor orbital, 145, for C2-C4 is 40.4 kJ/mol.
The interaction of lone pair donor orbital, 20, for C4 with
the second antibonding acceptor orbital, 144, for C2-O3 is 26.1 kJ/mol.
The interaction of antibonding donor orbital, 141, for O1-C2 with
the antibonding acceptor orbital, 146, for C4-H5 is 20.6 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.
24 ----- 1.608
23 ----- 1.110
22 ----- 0.572
21 ----- -0.622
20 -^--- -6.421
19 -^-v- -6.737
18 -^-v- -7.417
17 -^-v- -8.626
16 -^-v- -10.26
15 -^-v- -10.38
14 -^-v- -10.74
13 -^-v- -12.03
12 -^-v- -12.12
11 -^-v- -13.04
10 -^-v- -14.27
9 -^-v- -18.08
8 -^-v- -18.84
7 -^-v- -25.32
6 -^-v- -27.34
5 -^-v- -267.9
4 -^-v- -268.1
3 -^-v- -269.8
2 -^-v- -506.3
1 -^-v- -507.8
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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 = -267.8124393018 Hartrees
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