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.
Hybridization in the Best Lewis Structure
1. A bonding orbital for O1-C2 with 1.9947 electrons
__has 66.42% O 1 character in a sp2.49 hybrid
__has 33.58% C 2 character in a s0.82 p3 hybrid
2. A bonding orbital for O1-H12 with 1.9911 electrons
__has 72.77% O 1 character in a s0.78 p3 hybrid
__has 27.23% H12 character in a s orbital
3. A bonding orbital for C2-C3 with 1.9936 electrons
__has 50.27% C 2 character in a sp2.50 hybrid
__has 49.73% C 3 character in a sp2.58 hybrid
4. A bonding orbital for C2-C7 with 1.9935 electrons
__has 50.27% C 2 character in a sp2.50 hybrid
__has 49.73% C 7 character in a sp2.58 hybrid
5. A bonding orbital for C2-H11 with 1.9776 electrons
__has 57.91% C 2 character in a s0.83 p3 hybrid
__has 42.09% H11 character in a s orbital
6. A bonding orbital for C3-H4 with 1.9924 electrons
__has 59.86% C 3 character in a s0.96 p3 hybrid
__has 40.14% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 1.9924 electrons
__has 58.73% C 3 character in a s0.93 p3 hybrid
__has 41.27% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 1.9899 electrons
__has 59.26% C 3 character in a s0.94 p3 hybrid
__has 40.74% H 6 character in a s orbital
9. A bonding orbital for C7-H8 with 1.9899 electrons
__has 59.26% C 7 character in a s0.94 p3 hybrid
__has 40.74% H 8 character in a s orbital
10. A bonding orbital for C7-H9 with 1.9924 electrons
__has 58.73% C 7 character in a s0.93 p3 hybrid
__has 41.27% H 9 character in a s orbital
11. A bonding orbital for C7-H10 with 1.9924 electrons
__has 59.86% C 7 character in a s0.96 p3 hybrid
__has 40.14% H10 character in a s orbital
16. A lone pair orbital for O1 with 1.9847 electrons
__made from a sp0.97 hybrid
17. A lone pair orbital for O1 with 1.9718 electrons
__made from a p-pi orbital ( 99.96% p)
-With core pairs on: O 1 C 2 C 3 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 lone pair donor orbital, 17, for O1 with
the antibonding acceptor orbital, 136, for C2-C3 is 28.0 kJ/mol.
The interaction of the second lone pair donor orbital, 17, for O1 with
the antibonding acceptor orbital, 137, for C2-C7 is 28.7 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.
21 ----- 2.059
20 ----- 1.986
19 ----- 1.890
18 ----- 0.815
17 -^-v- -6.259
16 -^-v- -7.623
15 -^-v- -8.567
14 -^-v- -8.644
13 -^-v- -9.444
12 -^-v- -9.968
11 -^-v- -10.44
10 -^-v- -11.49
9 -^-v- -11.77
8 -^-v- -14.74
7 -^-v- -16.88
6 -^-v- -18.92
5 -^-v- -25.04
4 -^-v- -266.0 3 -^-v- -266.0
2 -^-v- -267.7
1 -^-v- -506.2
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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 = -194.4257886585 Hartrees
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