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 66.45% O 1 character in a sp2.44 hybrid
__has 33.55% C 2 character in a s0.90 p3 hybrid
2. A bonding orbital for O1-H14 with 0.9951 electrons
__has 72.94% O 1 character in a s0.77 p3 hybrid
__has 27.06% H14 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9945 electrons
__has 48.70% C 2 character in a sp2.31 hybrid
__has 51.30% C 3 character in a sp2.15 hybrid
4. A bonding orbital for C2-H12 with 0.9964 electrons
__has 55.64% C 2 character in a s0.91 p3 hybrid
__has 44.36% H12 character in a s orbital
5. A bonding orbital for C2-H13 with 0.9944 electrons
__has 56.99% C 2 character in a s0.93 p3 hybrid
__has 43.01% H13 character in a s orbital
6. A bonding orbital for C3-C4 with 0.9947 electrons
__has 51.26% C 3 character in a sp2.01 hybrid
__has 48.74% C 4 character in a sp2.40 hybrid
7. A bonding orbital for C3-C8 with 0.9954 electrons
__has 51.61% C 3 character in a sp1.92 hybrid
__has 48.39% C 8 character in a sp2.43 hybrid
8. A bonding orbital for C4-H5 with 0.9981 electrons
__has 57.27% C 4 character in a s0.89 p3 hybrid
__has 42.73% H 5 character in a s orbital
9. A bonding orbital for C4-H6 with 0.9965 electrons
__has 58.73% C 4 character in a s0.94 p3 hybrid
__has 41.27% H 6 character in a s orbital
10. A bonding orbital for C4-H7 with 0.9954 electrons
__has 59.03% C 4 character in a s0.94 p3 hybrid
__has 40.97% H 7 character in a s orbital
11. A bonding orbital for C8-H9 with 0.9957 electrons
__has 59.88% C 8 character in a s0.96 p3 hybrid
__has 40.12% H 9 character in a s orbital
12. A bonding orbital for C8-H10 with 0.9982 electrons
__has 56.71% C 8 character in a s0.88 p3 hybrid
__has 43.29% H10 character in a s orbital
13. A bonding orbital for C8-H11 with 0.9959 electrons
__has 58.74% C 8 character in a s0.94 p3 hybrid
__has 41.26% H11 character in a s orbital
19. A lone pair orbital for O1 with 0.9929 electrons
__made from a sp0.98 hybrid
20. A lone pair orbital for O1 with 0.9834 electrons
__made from a p3 hybrid
21. A lone pair orbital for C3 with 0.9272 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 4 C 8 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9978 electrons
__has 66.13% O 1 character in a sp2.47 hybrid
__has 33.87% C 2 character in a s0.88 p3 hybrid
2. A bonding orbital for O1-H14 with 0.9954 electrons
__has 72.94% O 1 character in a s0.77 p3 hybrid
__has 27.06% H14 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9953 electrons
__has 53.86% C 2 character in a sp2.18 hybrid
__has 46.14% C 3 character in a sp2.11 hybrid
4. A bonding orbital for C2-H12 with 0.9856 electrons
__has 59.24% C 2 character in a s0.91 p3 hybrid
__has 40.76% H12 character in a s orbital
5. A bonding orbital for C2-H13 with 0.9845 electrons
__has 60.23% C 2 character in a s0.89 p3 hybrid
__has 39.77% H13 character in a s orbital
6. A bonding orbital for C3-C4 with 0.9951 electrons
__has 46.24% C 3 character in a sp1.99 hybrid
__has 53.76% C 4 character in a sp2.28 hybrid
7. A bonding orbital for C3-C8 with 0.9959 electrons
__has 46.46% C 3 character in a sp1.91 hybrid
__has 53.54% C 8 character in a sp2.30 hybrid
8. A bonding orbital for C4-H5 with 0.9854 electrons
__has 61.55% C 4 character in a s0.90 p3 hybrid
__has 38.45% H 5 character in a s orbital
9. A bonding orbital for C4-H6 with 0.9917 electrons
__has 60.65% C 4 character in a s0.90 p3 hybrid
__has 39.35% H 6 character in a s orbital
10. A bonding orbital for C4-H7 with 0.9944 electrons
__has 59.89% C 4 character in a s0.91 p3 hybrid
__has 40.11% H 7 character in a s orbital
11. A bonding orbital for C8-H9 with 0.9937 electrons
__has 60.95% C 8 character in a s0.92 p3 hybrid
__has 39.05% H 9 character in a s orbital
12. A bonding orbital for C8-H10 with 0.9844 electrons
__has 61.51% C 8 character in a s0.89 p3 hybrid
__has 38.49% H10 character in a s orbital
13. A bonding orbital for C8-H11 with 0.9918 electrons
__has 60.60% C 8 character in a s0.91 p3 hybrid
__has 39.40% H11 character in a s orbital
19. A lone pair orbital for O1 with 0.9934 electrons
__made from a sp0.97 hybrid
20. A lone pair orbital for O1 with 0.9852 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 4 C 8 -
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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, 8, for C4-H5 with
the lone pair acceptor orbital, 21, for C3 is 26.5 kJ/mol.
The interaction of bonding donor orbital, 12, for C8-H10 with
the lone pair acceptor orbital, 21, for C3 is 27.7 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 ----- 2.209
24 ----- 2.008
23 ----- 1.453
22 ----- 0.461
21 -^--- -3.609
20 -^-v- -6.492
19 -^-v- -7.927
18 -^-v- -8.650
17 -^-v- -8.957
16 -^-v- -9.373
15 -^-v- -9.656
14 -^-v- -10.21
13 -^-v- -11.07
12 -^-v- -11.16
11 -^-v- -12.26
10 -^-v- -13.56
9 -^-v- -16.69
8 -^-v- -17.06
7 -^-v- -19.63
6 -^-v- -25.21
5 -^-v- -266.1
4 -^-v- -266.1
3 -^-v- -266.6
2 -^-v- -267.5
1 -^-v- -506.4
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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 = -233.0832868037 Hartrees
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