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.
Hybridization in the Best Lewis Structure
1. A bonding orbital for O1-C2 with 1.9924 electrons
__has 68.15% O 1 character in a sp2.31 hybrid
__has 31.85% C 2 character in a sp2.57 hybrid
2. A bonding orbital for O1-C11 with 1.9909 electrons
__has 68.38% O 1 character in a sp2.41 hybrid
__has 31.62% C11 character in a s0.86 p3 hybrid
3. A bonding orbital for C2-O3 with 1.9956 electrons
__has 35.61% C 2 character in a sp1.86 hybrid
__has 64.39% O 3 character in a sp1.53 hybrid
4. A bonding orbital for C2-O3 with 1.9929 electrons
__has 27.34% C 2 character in a p-pi orbital ( 99.35% p 0.65% d)
__has 72.66% O 3 character in a p-pi orbital ( 99.81% p 0.19% d)
5. A bonding orbital for C2-C4 with 1.9894 electrons
__has 48.73% C 2 character in a sp1.66 hybrid
__has 51.27% C 4 character in a s0.96 p3 hybrid
6. A bonding orbital for C4-C5 with 1.9913 electrons
__has 52.52% C 4 character in a sp2.29 hybrid
__has 47.48% C 5 character in a sp2.53 hybrid
7. A bonding orbital for C4-H9 with 1.9748 electrons
__has 60.07% C 4 character in a s0.88 p3 hybrid
__has 39.93% H 9 character in a s orbital
8. A bonding orbital for C4-H10 with 1.9749 electrons
__has 60.05% C 4 character in a s0.88 p3 hybrid
__has 39.95% H10 character in a s orbital
9. A bonding orbital for C5-H6 with 1.9916 electrons
__has 59.98% C 5 character in a s0.94 p3 hybrid
__has 40.02% H 6 character in a s orbital
10. A bonding orbital for C5-H7 with 1.9906 electrons
__has 59.13% C 5 character in a s0.94 p3 hybrid
__has 40.87% H 7 character in a s orbital
11. A bonding orbital for C5-H8 with 1.9916 electrons
__has 60.00% C 5 character in a s0.94 p3 hybrid
__has 40.00% H 8 character in a s orbital
12. A bonding orbital for C11-H12 with 1.9929 electrons
__has 59.42% C11 character in a sp2.86 hybrid
__has 40.58% H12 character in a s orbital
13. A bonding orbital for C11-H13 with 1.9953 electrons
__has 58.18% C11 character in a sp2.83 hybrid
__has 41.82% H13 character in a s orbital
14. A bonding orbital for C11-H14 with 1.9952 electrons
__has 58.16% C11 character in a sp2.83 hybrid
__has 41.84% H14 character in a s orbital
21. A lone pair orbital for O1 with 1.9689 electrons
__made from a sp1.46 hybrid
22. A lone pair orbital for O1 with 1.8648 electrons
__made from a p-pi orbital ( 99.95% p)
23. A lone pair orbital for O3 with 1.9786 electrons
__made from a sp0.64 hybrid
24. A lone pair orbital for O3 with 1.8835 electrons
__made from a p3 hybrid
182. A antibonding orbital for C2-O3 with 0.1372 electrons
__has 72.66% C 2 character in a p-pi orbital ( 99.35% p 0.65% d)
__has 27.34% O 3 character in 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 -
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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, 7, for C4-H9 with
the second antibonding acceptor orbital, 182, for C2-O3 is 24.8 kJ/mol.
The interaction of bonding donor orbital, 8, for C4-H10 with
the second antibonding acceptor orbital, 182, for C2-O3 is 24.7 kJ/mol.
The interaction of lone pair donor orbital, 21, for O1 with
the antibonding acceptor orbital, 183, for C2-C4 is 32.9 kJ/mol.
The interaction of the second lone pair donor orbital, 22, for O1 with
the second antibonding acceptor orbital, 182, for C2-O3 is 224. kJ/mol.
The interaction of the second lone pair donor orbital, 22, for O1 with
the antibonding acceptor orbital, 191, for C11-H13 is 29.6 kJ/mol.
The interaction of the second lone pair donor orbital, 22, for O1 with
the antibonding acceptor orbital, 192, for C11-H14 is 28.5 kJ/mol.
The interaction of the second lone pair donor orbital, 24, for O3 with
the antibonding acceptor orbital, 179, for O1-C2 is 170. kJ/mol.
The interaction of the second lone pair donor orbital, 24, for O3 with
the antibonding acceptor orbital, 183, for C2-C4 is 104. 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.
28 ----- 1.269
27 ----- 0.831
26 ----- 0.577
25 ----- -1.196
24 -^-v- -6.378
23 -^-v- -7.206
22 -^-v- -8.260
21 -^-v- -8.614
20 -^-v- -9.189
19 -^-v- -9.724
18 -^-v- -9.783
17 -^-v- -10.28
16 -^-v- -11.12
15 -^-v- -11.61
14 -^-v- -12.30
13 -^-v- -12.64
12 -^-v- -13.91
11 -^-v- -16.18
10 -^-v- -18.09
9 -^-v- -19.45
8 -^-v- -25.19
7 -^-v- -27.22
6 -^-v- -266.2
5 -^-v- -267.1
4 -^-v- -268.1
3 -^-v- -269.7
2 -^-v- -506.0
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 = -307.8008465868 Hartrees
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