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.
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 0.9968 electrons
__has 68.26% O 1 character in a sp2.57 hybrid
__has 31.74% C 2 character in a s0.87 p3 hybrid
2. A bonding orbital for O1-C6 with 0.9972 electrons
__has 67.77% O 1 character in a sp2.39 hybrid
__has 32.23% C 6 character in a sp2.57 hybrid
3. A bonding orbital for C2-H3 with 0.9968 electrons
__has 58.89% C 2 character in a sp2.83 hybrid
__has 41.11% H 3 character in a s orbital
4. A bonding orbital for C2-H4 with 0.9983 electrons
__has 57.82% C 2 character in a sp2.86 hybrid
__has 42.18% H 4 character in a s orbital
5. A bonding orbital for C2-H5 with 0.9983 electrons
__has 57.79% C 2 character in a sp2.86 hybrid
__has 42.21% H 5 character in a s orbital
6. A bonding orbital for C6-H7 with 0.9948 electrons
__has 60.49% C 6 character in a sp1.77 hybrid
__has 39.51% H 7 character in a s orbital
7. A bonding orbital for C6-H8 with 0.9963 electrons
__has 59.75% C 6 character in a sp1.76 hybrid
__has 40.25% H 8 character in a s orbital
11. A lone pair orbital for O1 with 0.9867 electrons
__made from a sp1.34 hybrid
12. A lone pair orbital for O1 with 0.9823 electrons
__made from a p3 hybrid
13. A lone pair orbital for C6 with 0.9941 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 6 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9967 electrons
__has 67.54% O 1 character in a sp2.57 hybrid
__has 32.46% C 2 character in a s0.87 p3 hybrid
2. A bonding orbital for O1-C6 with 0.9977 electrons
__has 70.22% O 1 character in a sp2.08 hybrid
__has 29.78% C 6 character in a sp2.45 hybrid
3. A bonding orbital for C2-H3 with 0.9972 electrons
__has 58.81% C 2 character in a sp2.86 hybrid
__has 41.19% H 3 character in a s orbital
4. A bonding orbital for C2-H4 with 0.9981 electrons
__has 58.11% C 2 character in a sp2.85 hybrid
__has 41.89% H 4 character in a s orbital
5. A bonding orbital for C2-H5 with 0.9981 electrons
__has 58.07% C 2 character in a sp2.86 hybrid
__has 41.93% H 5 character in a s orbital
6. A bonding orbital for C6-H7 with 0.9963 electrons
__has 54.76% C 6 character in a sp1.82 hybrid
__has 45.24% H 7 character in a s orbital
7. A bonding orbital for C6-H8 with 0.9979 electrons
__has 53.98% C 6 character in a sp1.79 hybrid
__has 46.02% H 8 character in a s orbital
11. A lone pair orbital for O1 with 0.9856 electrons
__made from a sp1.50 hybrid
12. A lone pair orbital for O1 with 0.8977 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 6 -
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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, 12, for O1 with
the lone pair acceptor orbital, 13, for C6 is 202. 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.
17 ----- 3.128
16 ----- 2.056
15 ----- 1.689
14 ----- 0.845
13 -^--- -3.525
12 -^-v- -8.199
11 -^-v- -8.259
10 -^-v- -9.634
9 -^-v- -11.44
8 -^-v- -12.00
7 -^-v- -12.34
6 -^-v- -15.30
5 -^-v- -18.03
4 -^-v- -26.49
3 -^-v- -267.3
2 -^-v- -267.7
1 -^-v- -507.6
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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 = -154.4183304498 Hartrees
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