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 0.9981 electrons
__has 66.68% O 1 character in a sp2.07 hybrid
__has 33.32% C 2 character in a sp2.05 hybrid
2. A bonding orbital for O1-C11 with 0.9925 electrons
__has 73.49% O 1 character in a sp2.04 hybrid
__has 26.51% C11 character in a s0.73 p3 hybrid
3. A bonding orbital for C2-O3 with 0.9981 electrons
__has 32.83% C 2 character in a sp2.14 hybrid
__has 67.17% O 3 character in a sp1.82 hybrid
4. A bonding orbital for C2-C4 with 0.9949 electrons
__has 52.02% C 2 character in a sp1.78 hybrid
__has 47.98% C 4 character in a s0.70 p3 hybrid
5. A bonding orbital for C4-C5 with 0.9970 electrons
__has 54.53% C 4 character in a sp1.91 hybrid
__has 45.47% C 5 character in a sp2.58 hybrid
6. A bonding orbital for C4-H9 with 0.9854 electrons
__has 61.95% C 4 character in a s0.92 p3 hybrid
__has 38.05% H 9 character in a s orbital
7. A bonding orbital for C4-H10 with 0.9853 electrons
__has 61.90% C 4 character in a s0.91 p3 hybrid
__has 38.10% H10 character in a s orbital
8. A bonding orbital for C5-H6 with 0.9951 electrons
__has 60.97% C 5 character in a s0.97 p3 hybrid
__has 39.03% H 6 character in a s orbital
9. A bonding orbital for C5-H7 with 0.9899 electrons
__has 61.66% C 5 character in a s0.90 p3 hybrid
__has 38.34% H 7 character in a s orbital
10. A bonding orbital for C5-H8 with 0.9951 electrons
__has 60.97% C 5 character in a s0.97 p3 hybrid
__has 39.03% H 8 character in a s orbital
11. A bonding orbital for C11-H12 with 0.9958 electrons
__has 61.50% C11 character in a sp2.80 hybrid
__has 38.50% H12 character in a s orbital
12. A bonding orbital for C11-H13 with 0.9966 electrons
__has 60.03% C11 character in a sp2.67 hybrid
__has 39.97% H13 character in a s orbital
13. A bonding orbital for C11-H14 with 0.9965 electrons
__has 59.93% C11 character in a sp2.68 hybrid
__has 40.07% H14 character in a s orbital
20. A lone pair orbital for O1 with 0.9804 electrons
__made from a sp1.87 hybrid
21. A lone pair orbital for O1 with 0.8835 electrons
__made from a p3 hybrid
22. A lone pair orbital for C2 with 0.2479 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)
23. A lone pair orbital for O3 with 0.9919 electrons
__made from a sp0.56 hybrid
24. A lone pair orbital for O3 with 0.9706 electrons
__made from a p3 hybrid
25. A lone pair orbital for O3 with 0.8788 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)
-With core pairs on: O 1 C 2 O 3 C 4 C 5 C11 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9928 electrons
__has 63.44% O 1 character in a sp2.37 hybrid
__has 36.56% C 2 character in a sp1.91 hybrid
2. A bonding orbital for O1-C11 with 0.9920 electrons
__has 73.38% O 1 character in a sp2.04 hybrid
__has 26.62% C11 character in a s0.73 p3 hybrid
3. A bonding orbital for C2-O3 with 0.9977 electrons
__has 36.24% C 2 character in a sp2.15 hybrid
__has 63.76% O 3 character in a sp1.60 hybrid
4. A bonding orbital for C2-C4 with 0.9497 electrons
__has 59.46% C 2 character in a sp1.91 hybrid
__has 40.54% C 4 character in a s0.67 p3 hybrid
5. A bonding orbital for C4-C5 with 0.9968 electrons
__has 53.93% C 4 character in a sp1.92 hybrid
__has 46.07% C 5 character in a sp2.56 hybrid
6. A bonding orbital for C4-H9 with 0.9804 electrons
__has 61.73% C 4 character in a s0.94 p3 hybrid
__has 38.27% H 9 character in a s orbital
7. A bonding orbital for C4-H10 with 0.9802 electrons
__has 61.67% C 4 character in a s0.93 p3 hybrid
__has 38.33% H10 character in a s orbital
8. A bonding orbital for C5-H6 with 0.9950 electrons
__has 61.04% C 5 character in a s0.98 p3 hybrid
__has 38.96% H 6 character in a s orbital
9. A bonding orbital for C5-H7 with 0.9889 electrons
__has 61.62% C 5 character in a s0.89 p3 hybrid
__has 38.38% H 7 character in a s orbital
10. A bonding orbital for C5-H8 with 0.9950 electrons
__has 61.04% C 5 character in a s0.97 p3 hybrid
__has 38.96% H 8 character in a s orbital
11. A bonding orbital for C11-H12 with 0.9945 electrons
__has 61.63% C11 character in a sp2.78 hybrid
__has 38.37% H12 character in a s orbital
12. A bonding orbital for C11-H13 with 0.9967 electrons
__has 59.99% C11 character in a sp2.68 hybrid
__has 40.01% H13 character in a s orbital
13. A bonding orbital for C11-H14 with 0.9967 electrons
__has 59.89% C11 character in a sp2.69 hybrid
__has 40.11% H14 character in a s orbital
20. A lone pair orbital for O1 with 0.9819 electrons
__made from a sp1.65 hybrid
21. A lone pair orbital for O1 with 0.8922 electrons
__made from a p3 hybrid
22. A lone pair orbital for C2 with 0.2884 electrons
__made from a p-pi orbital ( 99.76% p 0.24% d)
23. A lone pair orbital for O3 with 0.9911 electrons
__made from a sp0.61 hybrid
24. A lone pair orbital for O3 with 0.8274 electrons
__made from a p-pi orbital ( 99.81% p 0.19% d)
-With core pairs on: O 1 C 2 O 3 C 4 C 5 C11 -
Top of page.
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, 4, for C2-C4 with
the third lone pair acceptor orbital, 25, for O3 is 88.5 kJ/mol.
The interaction of bonding donor orbital, 9, for C5-H7 with
the antibonding acceptor orbital, 183, for C2-C4 is 19.9 kJ/mol.
The interaction of lone pair donor orbital, 20, for O1 with
the antibonding acceptor orbital, 183, for C2-C4 is 22.3 kJ/mol.
The interaction of the second lone pair donor orbital, 21, for O1 with
the lone pair acceptor orbital, 22, for C2 is 259. kJ/mol.
The interaction of the second lone pair donor orbital, 24, for O3 with
the lone pair acceptor orbital, 22, for C2 is 515. kJ/mol.
Top of page.
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.
28 ----- -3.451
27 ----- -4.024
26 ----- -5.041
25 ----- -7.706
24 -^--- -13.44
23 -^-v- -13.93
22 -^-v- -14.14
21 -^-v- -14.70
20 -^-v- -14.81
19 -^-v- -15.46
18 -^-v- -16.19
17 -^-v- -16.58
16 -^-v- -16.93
15 -^-v- -18.19
14 -^-v- -18.67
13 -^-v- -18.92
12 -^-v- -19.83
11 -^-v- -21.94
10 -^-v- -24.36
9 -^-v- -25.45
8 -^-v- -32.83
7 -^-v- -34.62
6 -^-v- -271.5
5 -^-v- -273.5
4 -^-v- -273.7
3 -^-v- -276.9
2 -^-v- -514.5
1 -^-v- -514.8
Top of page.
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 = -307.4449405727 Hartrees
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