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 0.9920 electrons
__has 48.75% C 1 character in a sp2.42 hybrid
__has 51.25% C 2 character in a sp2.12 hybrid
2. A bonding orbital for C1-H3 with 0.9903 electrons
__has 62.68% C 1 character in a s0.96 p3 hybrid
__has 37.32% H 3 character in a s orbital
3. A bonding orbital for C1-H4 with 0.9896 electrons
__has 62.20% C 1 character in a s0.86 p3 hybrid
__has 37.80% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 0.9923 electrons
__has 61.76% C 1 character in a s0.95 p3 hybrid
__has 38.24% H 5 character in a s orbital
5. A bonding orbital for C2-C6 with 0.9847 electrons
__has 44.68% C 2 character in a s0.56 p3 hybrid
__has 55.32% C 6 character in a s0.81 p3 hybrid
6. A bonding orbital for C2-C7 with 0.9883 electrons
__has 51.89% C 2 character in a sp2.21 hybrid
__has 48.11% C 7 character in a sp2.44 hybrid
7. A bonding orbital for C2-O8 with 0.9959 electrons
__has 28.13% C 2 character in a s0.82 p3 hybrid
__has 71.87% O 8 character in a sp1.65 hybrid
8. A bonding orbital for C6-H9 with 0.9961 electrons
__has 62.38% C 6 character in a sp2.92 hybrid
__has 37.62% H 9 character in a s orbital
9. A bonding orbital for C6-H10 with 0.9966 electrons
__has 62.64% C 6 character in a sp2.79 hybrid
__has 37.36% H10 character in a s orbital
10. A bonding orbital for C6-H11 with 0.9965 electrons
__has 63.45% C 6 character in a sp2.70 hybrid
__has 36.55% H11 character in a s orbital
11. A bonding orbital for C7-H12 with 0.9912 electrons
__has 62.04% C 7 character in a s0.95 p3 hybrid
__has 37.96% H12 character in a s orbital
12. A bonding orbital for C7-H13 with 0.9923 electrons
__has 62.67% C 7 character in a s0.98 p3 hybrid
__has 37.33% H13 character in a s orbital
13. A bonding orbital for C7-H14 with 0.9896 electrons
__has 62.00% C 7 character in a s0.85 p3 hybrid
__has 38.00% H14 character in a s orbital
14. A bonding orbital for O8-H15 with 0.9932 electrons
__has 78.59% O 8 character in a s0.82 p3 hybrid
__has 21.41% H15 character in a s orbital
20. A lone pair orbital for O8 with 0.9903 electrons
__made from a sp1.43 hybrid
21. A lone pair orbital for O8 with 0.9799 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 6 C 7 O 8 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9799 electrons
__has 47.57% C 1 character in a sp2.51 hybrid
__has 52.43% C 2 character in a sp1.67 hybrid
2. A bonding orbital for C1-H3 with 0.9909 electrons
__has 62.47% C 1 character in a s0.95 p3 hybrid
__has 37.53% H 3 character in a s orbital
3. A bonding orbital for C1-H4 with 0.9698 electrons
__has 63.87% C 1 character in a s0.94 p3 hybrid
__has 36.13% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 0.9910 electrons
__has 61.81% C 1 character in a s0.92 p3 hybrid
__has 38.19% H 5 character in a s orbital
5. A bonding orbital for C2-C7 with 0.9716 electrons
__has 53.59% C 2 character in a sp1.66 hybrid
__has 46.41% C 7 character in a sp2.55 hybrid
6. A bonding orbital for C2-O8 with 0.9934 electrons
__has 28.54% C 2 character in a s0.78 p3 hybrid
__has 71.46% O 8 character in a sp1.60 hybrid
7. A bonding orbital for C2-O8 with 0.9251 electrons
__has 24.97% C 2 character in a s0.14 p3 hybrid
__has 75.03% O 8 character in a p3 hybrid
8. A bonding orbital for C6-H9 with 0.9824 electrons
__has 62.17% C 6 character in a sp2.07 hybrid
__has 37.83% H 9 character in a s orbital
9. A bonding orbital for C6-H10 with 0.9907 electrons
__has 61.32% C 6 character in a sp2.15 hybrid
__has 38.68% H10 character in a s orbital
10. A bonding orbital for C6-H11 with 0.9918 electrons
__has 61.91% C 6 character in a sp2.13 hybrid
__has 38.09% H11 character in a s orbital
11. A bonding orbital for C7-H12 with 0.9918 electrons
__has 61.76% C 7 character in a s0.94 p3 hybrid
__has 38.24% H12 character in a s orbital
12. A bonding orbital for C7-H13 with 0.9912 electrons
__has 62.65% C 7 character in a s0.95 p3 hybrid
__has 37.35% H13 character in a s orbital
13. A bonding orbital for C7-H14 with 0.9663 electrons
__has 63.81% C 7 character in a s0.94 p3 hybrid
__has 36.19% H14 character in a s orbital
14. A bonding orbital for O8-H15 with 0.9932 electrons
__has 77.13% O 8 character in a s0.83 p3 hybrid
__has 22.87% H15 character in a s orbital
21. A lone pair orbital for O8 with 0.9897 electrons
__made from a sp1.53 hybrid
-With core pairs on: C 1 C 2 C 6 C 7 O 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, 3, for C1-H4 with
the second antibonding acceptor orbital, 118, for C2-O8 is 44.7 kJ/mol.
The interaction of bonding donor orbital, 13, for C7-H14 with
the second antibonding acceptor orbital, 118, for C2-O8 is 49.7 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the lone pair acceptor orbital, 20, for C6 is 49.7 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C7 with
the lone pair acceptor orbital, 20, for C6 is 61.8 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-O8 with
the lone pair acceptor orbital, 20, for C6 is 6.94 kJ/mol.
The interaction of the second bonding donor orbital, 7, for C2-O8 with
the lone pair acceptor orbital, 20, for C6 is 156. kJ/mol.
The interaction of bonding donor orbital, 8, for C6-H9 with
the antibonding acceptor orbital, 117, for C2-O8 is 8.95 kJ/mol.
The interaction of bonding donor orbital, 8, for C6-H9 with
the second antibonding acceptor orbital, 118, for C2-O8 is 46.4 kJ/mol.
The interaction of bonding donor orbital, 9, for C6-H10 with
the second antibonding acceptor orbital, 118, for C2-O8 is 37.0 kJ/mol.
The interaction of bonding donor orbital, 10, for C6-H11 with
the antibonding acceptor orbital, 112, for C1-C2 is 2.38 kJ/mol.
The interaction of bonding donor orbital, 10, for C6-H11 with
the second antibonding acceptor orbital, 118, for C2-O8 is 32.7 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.
25 ----- -2.847
24 ----- -3.386
23 ----- -4.591
22 ----- -5.277
21 -^--- -12.73
20 -^-v- -14.28
19 -^-v- -14.48
18 -^-v- -14.58
17 -^-v- -14.67
16 -^-v- -15.18
15 -^-v- -15.84
14 -^-v- -16.03
13 -^-v- -17.23
12 -^-v- -17.28
11 -^-v- -18.17
10 -^-v- -21.00
9 -^-v- -22.78
8 -^-v- -22.93
7 -^-v- -25.51
6 -^-v- -33.10
5 -^-v- -271.6
4 -^-v- -271.8
3 -^-v- -273.0
2 -^-v- -275.2
1 -^-v- -514.3
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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 = -233.4061215744 Hartrees
*The Lewis Structure (NBO) analysis was done at the DZVP level
without diffuse functions to decrease the size of the calculation
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