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 C1-C2 with 0.9984 electrons
__has 47.09% C 1 character in a sp2.68 hybrid
__has 52.91% C 2 character in a sp1.84 hybrid
2. A bonding orbital for C1-H6 with 0.9879 electrons
__has 62.39% C 1 character in a s0.96 p3 hybrid
__has 37.61% H 6 character in a s orbital
3. A bonding orbital for C1-H7 with 0.9945 electrons
__has 60.89% C 1 character in a s0.96 p3 hybrid
__has 39.11% H 7 character in a s orbital
4. A bonding orbital for C1-H8 with 0.9944 electrons
__has 60.78% C 1 character in a s0.96 p3 hybrid
__has 39.22% H 8 character in a s orbital
5. A bonding orbital for C2-O3 with 0.9966 electrons
__has 26.42% C 2 character in a s0.73 p3 hybrid
__has 73.58% O 3 character in a sp2.10 hybrid
6. A bonding orbital for C2-H9 with 0.9937 electrons
__has 60.18% C 2 character in a s0.89 p3 hybrid
__has 39.82% H 9 character in a s orbital
7. A bonding orbital for C2-H10 with 0.9937 electrons
__has 60.21% C 2 character in a s0.88 p3 hybrid
__has 39.79% H10 character in a s orbital
8. A bonding orbital for O3-C4 with 0.9968 electrons
__has 73.93% O 3 character in a sp2.10 hybrid
__has 26.07% C 4 character in a s0.71 p3 hybrid
9. A bonding orbital for C4-C5 with 0.9971 electrons
__has 52.49% C 4 character in a sp2.40 hybrid
__has 47.51% C 5 character in a s0.99 p3 hybrid
10. A bonding orbital for C4-H11 with 0.9942 electrons
__has 60.24% C 4 character in a s0.95 p3 hybrid
__has 39.76% H11 character in a s orbital
11. A bonding orbital for C4-H12 with 0.9955 electrons
__has 60.82% C 4 character in a sp2.61 hybrid
__has 39.18% H12 character in a s orbital
12. A bonding orbital for C5-H13 with 0.9960 electrons
__has 60.61% C 5 character in a s0.99 p3 hybrid
__has 39.39% H13 character in a s orbital
13. A bonding orbital for C5-H14 with 0.9960 electrons
__has 61.50% C 5 character in a sp2.86 hybrid
__has 38.50% H14 character in a s orbital
14. A bonding orbital for C5-H15 with 0.9921 electrons
__has 61.56% C 5 character in a s0.97 p3 hybrid
__has 38.44% H15 character in a s orbital
20. A lone pair orbital for O3 with 0.9894 electrons
__made from a sp1.83 hybrid
21. A lone pair orbital for O3 with 0.9871 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 O 3 C 4 C 5 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9983 electrons
__has 47.01% C 1 character in a sp2.68 hybrid
__has 52.99% C 2 character in a sp1.87 hybrid
2. A bonding orbital for C1-H6 with 0.9891 electrons
__has 62.24% C 1 character in a s0.96 p3 hybrid
__has 37.76% H 6 character in a s orbital
3. A bonding orbital for C1-H7 with 0.9945 electrons
__has 60.96% C 1 character in a s0.96 p3 hybrid
__has 39.04% H 7 character in a s orbital
4. A bonding orbital for C1-H8 with 0.9945 electrons
__has 60.84% C 1 character in a s0.96 p3 hybrid
__has 39.16% H 8 character in a s orbital
5. A bonding orbital for C2-O3 with 0.9968 electrons
__has 31.10% C 2 character in a s0.76 p3 hybrid
__has 68.90% O 3 character in a sp2.03 hybrid
6. A bonding orbital for C2-H9 with 0.9597 electrons
__has 64.01% C 2 character in a s0.88 p3 hybrid
__has 35.99% H 9 character in a s orbital
7. A bonding orbital for C2-H10 with 0.9588 electrons
__has 64.17% C 2 character in a s0.87 p3 hybrid
__has 35.83% H10 character in a s orbital
8. A bonding orbital for O3-C4 with 0.9970 electrons
__has 69.32% O 3 character in a sp2.03 hybrid
__has 30.68% C 4 character in a s0.74 p3 hybrid
9. A bonding orbital for C4-C5 with 0.9638 electrons
__has 56.55% C 4 character in a sp2.35 hybrid
__has 43.45% C 5 character in a s0.95 p3 hybrid
10. A bonding orbital for C4-H11 with 0.9688 electrons
__has 63.14% C 4 character in a s0.91 p3 hybrid
__has 36.86% H11 character in a s orbital
11. A bonding orbital for C4-H12 with 0.9946 electrons
__has 61.07% C 4 character in a sp2.65 hybrid
__has 38.93% H12 character in a s orbital
12. A bonding orbital for C5-H13 with 0.9957 electrons
__has 60.29% C 5 character in a sp2.96 hybrid
__has 39.71% H13 character in a s orbital
13. A bonding orbital for C5-H14 with 0.9962 electrons
__has 61.09% C 5 character in a sp2.86 hybrid
__has 38.91% H14 character in a s orbital
14. A bonding orbital for C5-H15 with 0.9884 electrons
__has 61.73% C 5 character in a s0.99 p3 hybrid
__has 38.27% H15 character in a s orbital
20. A lone pair orbital for O3 with 0.9874 electrons
__made from a sp1.92 hybrid
21. A lone pair orbital for O3 with 0.1336 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 O 3 C 4 C 5 -
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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, 6, for C2-H9 with
the second lone pair acceptor orbital, 21, for O3 is 46.4 kJ/mol.
The interaction of bonding donor orbital, 7, for C2-H10 with
the second lone pair acceptor orbital, 21, for O3 is 48.6 kJ/mol.
The interaction of bonding donor orbital, 9, for C4-C5 with
the second lone pair acceptor orbital, 21, for O3 is 39.3 kJ/mol.
The interaction of bonding donor orbital, 10, for C4-H11 with
the second lone pair acceptor orbital, 21, for O3 is 34.1 kJ/mol.
Top of page.
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.
25 ----- -3.010
24 ----- -3.233
23 ----- -3.560
22 ----- -4.502
21 -^--- -12.84
20 -^-v- -13.73
19 -^-v- -14.25
18 -^-v- -14.45
17 -^-v- -14.57
16 -^-v- -14.84
15 -^-v- -15.64
14 -^-v- -16.15
13 -^-v- -17.49
12 -^-v- -18.33
11 -^-v- -18.81
10 -^-v- -19.90
9 -^-v- -21.93
8 -^-v- -23.76
7 -^-v- -25.42
6 -^-v- -33.32
5 -^-v- -271.5
4 -^-v- -271.5
3 -^-v- -273.8
2 -^-v- -274.1
1 -^-v- -515.1
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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 = -233.4001888391 Hartrees
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