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 0.9987 electrons
__has 73.13% C 1 character in a p3 hybrid
__has 26.87% C 2 character in a p-pi orbital ( 99.58% p 0.42% d)
2. A bonding orbital for C1-C2 with 0.9983 electrons
__has 49.60% C 1 character in a sp1.84 hybrid
__has 50.40% C 2 character in a sp1.57 hybrid
3. A bonding orbital for C1-H6 with 0.9946 electrons
__has 62.70% C 1 character in a sp2.02 hybrid
__has 37.30% H 6 character in a s orbital
4. A bonding orbital for C1-H7 with 0.9929 electrons
__has 63.32% C 1 character in a sp2.12 hybrid
__has 36.68% H 7 character in a s orbital
5. A bonding orbital for C2-O3 with 0.9981 electrons
__has 31.67% C 2 character in a sp2.42 hybrid
__has 68.33% O 3 character in a sp1.89 hybrid
6. A bonding orbital for C2-H8 with 0.9918 electrons
__has 61.40% C 2 character in a sp2.10 hybrid
__has 38.60% H 8 character in a s orbital
7. A bonding orbital for O3-C4 with 0.9945 electrons
__has 74.60% O 3 character in a sp2.26 hybrid
__has 25.40% C 4 character in a s0.64 p3 hybrid
8. A bonding orbital for C4-C5 with 0.9966 electrons
__has 52.64% C 4 character in a sp2.12 hybrid
__has 47.36% C 5 character in a sp2.75 hybrid
9. A bonding orbital for C4-H9 with 0.9930 electrons
__has 60.78% C 4 character in a s0.98 p3 hybrid
__has 39.22% H 9 character in a s orbital
10. A bonding orbital for C4-H10 with 0.9945 electrons
__has 59.11% C 4 character in a sp2.86 hybrid
__has 40.89% H10 character in a s orbital
11. A bonding orbital for C5-H11 with 0.9901 electrons
__has 61.24% C 5 character in a s0.93 p3 hybrid
__has 38.76% H11 character in a s orbital
12. A bonding orbital for C5-H12 with 0.9950 electrons
__has 61.27% C 5 character in a sp2.97 hybrid
__has 38.73% H12 character in a s orbital
13. A bonding orbital for C5-H13 with 0.9954 electrons
__has 60.08% C 5 character in a s0.97 p3 hybrid
__has 39.92% H13 character in a s orbital
19. A lone pair orbital for O3 with 0.9846 electrons
__made from a sp1.87 hybrid
20. A lone pair orbital for O3 with 0.9290 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 46.62% C 1 character in a sp1.87 hybrid
__has 53.38% C 2 character in a sp1.54 hybrid
2. A bonding orbital for C1-H6 with 0.9952 electrons
__has 58.75% C 1 character in a sp2.01 hybrid
__has 41.25% H 6 character in a s orbital
3. A bonding orbital for C1-H7 with 0.9938 electrons
__has 59.34% C 1 character in a sp2.11 hybrid
__has 40.66% H 7 character in a s orbital
4. A bonding orbital for C2-O3 with 0.9981 electrons
__has 33.58% C 2 character in a sp2.41 hybrid
__has 66.42% O 3 character in a sp1.85 hybrid
5. A bonding orbital for C2-O3 with 0.9763 electrons
__has 32.37% C 2 character in a p3 hybrid
__has 67.63% O 3 character in a p-pi orbital ( 99.88% p 0.12% d)
6. A bonding orbital for C2-H8 with 0.9914 electrons
__has 61.67% C 2 character in a sp2.16 hybrid
__has 38.33% H 8 character in a s orbital
7. A bonding orbital for O3-C4 with 0.9946 electrons
__has 72.66% O 3 character in a sp2.22 hybrid
__has 27.34% C 4 character in a s0.65 p3 hybrid
8. A bonding orbital for C4-C5 with 0.9922 electrons
__has 53.15% C 4 character in a sp2.14 hybrid
__has 46.85% C 5 character in a sp2.76 hybrid
9. A bonding orbital for C4-H9 with 0.9886 electrons
__has 61.20% C 4 character in a s0.98 p3 hybrid
__has 38.80% H 9 character in a s orbital
10. A bonding orbital for C4-H10 with 0.9945 electrons
__has 59.22% C 4 character in a sp2.87 hybrid
__has 40.78% H10 character in a s orbital
11. A bonding orbital for C5-H11 with 0.9898 electrons
__has 61.23% C 5 character in a s0.93 p3 hybrid
__has 38.77% H11 character in a s orbital
12. A bonding orbital for C5-H12 with 0.9950 electrons
__has 61.22% C 5 character in a sp2.97 hybrid
__has 38.78% H12 character in a s orbital
13. A bonding orbital for C5-H13 with 0.9952 electrons
__has 60.02% C 5 character in a s0.98 p3 hybrid
__has 39.98% H13 character in a s orbital
20. A lone pair orbital for O3 with 0.9839 electrons
__made from a sp1.93 hybrid
-With core pairs on: C 1 C 2 O 3 C 4 C 5 -
Top of page.
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 bonding donor orbital, 5, for C2-O3 with
the lone pair acceptor orbital, 19, for C1 is 34.3 kJ/mol.
The interaction of lone pair donor orbital, 20, for O3 with
the antibonding acceptor orbital, 156, for C1-C2 is 20.2 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.
24 ----- -3.195
23 ----- -3.751
22 ----- -4.661
21 ----- -7.758
20 -^--- -12.74
19 -^-v- -13.55
18 -^-v- -14.08
17 -^-v- -14.62
16 -^-v- -14.81
15 -^-v- -16.03
14 -^-v- -16.39
13 -^-v- -17.44
12 -^-v- -18.44
11 -^-v- -19.21
10 -^-v- -19.70
9 -^-v- -21.86
8 -^-v- -24.46
7 -^-v- -25.70
6 -^-v- -33.82
5 -^-v- -271.0
4 -^-v- -273.6
3 -^-v- -273.8
2 -^-v- -275.2
1 -^-v- -515.1
Top of page.
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 = -232.1934419441 Hartrees
Top of page.
-> Return to Molecular Structure Page.
-> Return to Chemistry Home Page