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 0.9978 electrons
__has 67.30% O 1 character in a sp2.29 hybrid
__has 32.70% C 2 character in a sp2.95 hybrid
2. A bonding orbital for O1-H11 with 0.9953 electrons
__has 73.81% O 1 character in a s0.81 p3 hybrid
__has 26.19% H11 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9963 electrons
__has 49.34% C 2 character in a sp1.81 hybrid
__has 50.66% C 3 character in a sp2.68 hybrid
4. A bonding orbital for C2-H10 with 0.9923 electrons
__has 59.18% C 2 character in a sp2.32 hybrid
__has 40.82% H10 character in a s orbital
5. A bonding orbital for C3-C4 with 0.9958 electrons
__has 51.08% C 3 character in a sp2.44 hybrid
__has 48.92% C 4 character in a sp2.48 hybrid
6. A bonding orbital for C3-H8 with 0.9922 electrons
__has 58.12% C 3 character in a s0.87 p3 hybrid
__has 41.88% H 8 character in a s orbital
7. A bonding orbital for C3-H9 with 0.9950 electrons
__has 57.11% C 3 character in a s0.82 p3 hybrid
__has 42.89% H 9 character in a s orbital
8. A bonding orbital for C4-H5 with 0.9962 electrons
__has 59.39% C 4 character in a s0.93 p3 hybrid
__has 40.61% H 5 character in a s orbital
9. A bonding orbital for C4-H6 with 0.9961 electrons
__has 59.19% C 4 character in a s0.92 p3 hybrid
__has 40.81% H 6 character in a s orbital
10. A bonding orbital for C4-H7 with 0.9960 electrons
__has 59.38% C 4 character in a s0.94 p3 hybrid
__has 40.62% H 7 character in a s orbital
15. A lone pair orbital for O1 with 0.9951 electrons
__made from a s0.67 p3 hybrid
16. A lone pair orbital for O1 with 0.9916 electrons
__made from a sp2.32 hybrid
17. A lone pair orbital for C2 with 0.9712 electrons
__made from a s0.33 p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 4 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9983 electrons
__has 69.45% O 1 character in a sp2.06 hybrid
__has 30.55% C 2 character in a sp2.52 hybrid
2. A bonding orbital for O1-H11 with 0.9947 electrons
__has 73.39% O 1 character in a s0.79 p3 hybrid
__has 26.61% H11 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9963 electrons
__has 45.12% C 2 character in a sp1.63 hybrid
__has 54.88% C 3 character in a sp2.60 hybrid
4. A bonding orbital for C2-H10 with 0.9939 electrons
__has 54.43% C 2 character in a sp2.05 hybrid
__has 45.57% H10 character in a s orbital
5. A bonding orbital for C3-C4 with 0.9954 electrons
__has 51.71% C 3 character in a sp2.56 hybrid
__has 48.29% C 4 character in a sp2.51 hybrid
6. A bonding orbital for C3-H8 with 0.9906 electrons
__has 59.27% C 3 character in a s0.83 p3 hybrid
__has 40.73% H 8 character in a s orbital
7. A bonding orbital for C3-H9 with 0.9839 electrons
__has 61.54% C 3 character in a s0.88 p3 hybrid
__has 38.46% H 9 character in a s orbital
8. A bonding orbital for C4-H5 with 0.9964 electrons
__has 59.26% C 4 character in a s0.94 p3 hybrid
__has 40.74% H 5 character in a s orbital
9. A bonding orbital for C4-H6 with 0.9962 electrons
__has 59.05% C 4 character in a s0.93 p3 hybrid
__has 40.95% H 6 character in a s orbital
10. A bonding orbital for C4-H7 with 0.9965 electrons
__has 59.23% C 4 character in a s0.95 p3 hybrid
__has 40.77% H 7 character in a s orbital
15. A lone pair orbital for O1 with 0.9920 electrons
__made from a sp1.21 hybrid
16. A lone pair orbital for O1 with 0.9224 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 4 -
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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 C3-H9 with
the lone pair acceptor orbital, 17, for C2 is 26.3 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O1 with
the lone pair acceptor orbital, 17, for C2 is 167. 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.
21 ----- 2.421
20 ----- 2.214
19 ----- 1.497
18 ----- 0.499
17 -^--- -3.424
16 -^-v- -8.008
15 -^-v- -8.307
14 -^-v- -8.745
13 -^-v- -9.451
12 -^-v- -9.729
11 -^-v- -10.64
10 -^-v- -11.44
9 -^-v- -12.30
8 -^-v- -14.95
7 -^-v- -16.39
6 -^-v- -19.23
5 -^-v- -26.07
4 -^-v- -266.1
3 -^-v- -266.6
2 -^-v- -267.5
1 -^-v- -507.2
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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 = -193.7625984303 Hartrees
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