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 0.9990 electrons
__has 67.34% O 1 character in a sp1.87 hybrid
__has 32.66% C 2 character in a sp2.40 hybrid
2. A bonding orbital for O1-H7 with 0.9944 electrons
__has 77.76% O 1 character in a s0.89 p3 hybrid
__has 22.24% H 7 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9990 electrons
__has 29.27% C 2 character in a p-pi orbital ( 99.59% p 0.41% d)
__has 70.73% C 3 character in a p-pi orbital ( 99.83% p 0.17% d)
4. A bonding orbital for C2-C3 with 0.9981 electrons
__has 51.05% C 2 character in a sp1.62 hybrid
__has 48.95% C 3 character in a sp1.91 hybrid
5. A bonding orbital for C2-H6 with 0.9927 electrons
__has 62.29% C 2 character in a sp2.04 hybrid
__has 37.71% H 6 character in a s orbital
6. A bonding orbital for C3-H4 with 0.9950 electrons
__has 62.97% C 3 character in a sp2.01 hybrid
__has 37.03% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9936 electrons
__has 63.76% C 3 character in a sp2.05 hybrid
__has 36.24% H 5 character in a s orbital
11. A lone pair orbital for O1 with 0.9895 electrons
__made from a sp1.35 hybrid
12. A lone pair orbital for O1 with 0.9286 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
-With core pairs on: O 1 C 2 C 3 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9990 electrons
__has 66.49% O 1 character in a sp1.82 hybrid
__has 33.51% C 2 character in a sp2.39 hybrid
2. A bonding orbital for O1-C2 with 0.9898 electrons
__has 78.00% O 1 character in a p-pi orbital ( 99.87% p 0.12% d)
__has 22.00% C 2 character in a p-pi orbital ( 99.30% p 0.70% d)
3. A bonding orbital for O1-H7 with 0.9944 electrons
__has 76.81% O 1 character in a s0.90 p3 hybrid
__has 23.19% H 7 character in a s orbital
4. A bonding orbital for C2-C3 with 0.9983 electrons
__has 53.49% C 2 character in a sp1.59 hybrid
__has 46.51% C 3 character in a sp1.92 hybrid
5. A bonding orbital for C2-H6 with 0.9927 electrons
__has 61.79% C 2 character in a sp2.09 hybrid
__has 38.21% H 6 character in a s orbital
6. A bonding orbital for C3-H4 with 0.9958 electrons
__has 59.13% C 3 character in a sp2.01 hybrid
__has 40.87% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9945 electrons
__has 59.88% C 3 character in a sp2.05 hybrid
__has 40.12% H 5 character in a s orbital
11. A lone pair orbital for O1 with 0.9895 electrons
__made from a sp1.41 hybrid
-With core pairs on: O 1 C 2 C 3 -
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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.
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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.
16 ----- -3.546
15 ----- -4.029
14 ----- -5.810
13 ----- -8.928
12 -^--- -14.00
11 -^-v- -16.25
10 -^-v- -17.05
9 -^-v- -18.16
8 -^-v- -19.54
7 -^-v- -20.07
6 -^-v- -23.61
5 -^-v- -26.39
4 -^-v- -35.05
3 -^-v- -275.0
2 -^-v- -276.5
1 -^-v- -516.0
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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 = -153.5337247299 Hartrees
Note: This ion results from the McLafferty rearrangment of aldehydes. It
is the enol radical cation of acetaldehyde, or the vinyl alcohol radical
cation.
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