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 0.9973 electrons
__has 47.80% C 1 character in a sp2.47 hybrid
__has 52.20% C 2 character in a sp2.22 hybrid
2. A bonding orbital for C1-H3 with 0.9954 electrons
__has 59.08% C 1 character in a s0.89 p3 hybrid
__has 40.92% H 3 character in a s orbital
3. A bonding orbital for C1-H4 with 0.9937 electrons
__has 61.44% C 1 character in a s0.95 p3 hybrid
__has 38.56% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 0.9958 electrons
__has 59.68% C 1 character in a s0.96 p3 hybrid
__has 40.32% H 5 character in a s orbital
5. A bonding orbital for C2-C6 with 0.9875 electrons
__has 45.98% C 2 character in a sp2.80 hybrid
__has 54.02% C 6 character in a sp2.24 hybrid
6. A bonding orbital for C2-H7 with 0.9854 electrons
__has 60.70% C 2 character in a s0.73 p3 hybrid
__has 39.30% H 7 character in a s orbital
7. A bonding orbital for C2-H8 with 0.9919 electrons
__has 60.59% C 2 character in a s0.91 p3 hybrid
__has 39.41% H 8 character in a s orbital
8. A bonding orbital for C6-C9 with 0.9936 electrons
__has 48.34% C 6 character in a s0.77 p3 hybrid
__has 51.66% C 9 character in a sp2.00 hybrid
9. A bonding orbital for C6-H10 with 0.9899 electrons
__has 61.62% C 6 character in a s0.95 p3 hybrid
__has 38.38% H10 character in a s orbital
10. A bonding orbital for C6-H11 with 0.9899 electrons
__has 62.51% C 6 character in a s0.98 p3 hybrid
__has 37.49% H11 character in a s orbital
11. A bonding orbital for C9-C12 with 0.9968 electrons
__has 50.47% C 9 character in a sp1.71 hybrid
__has 49.53% C12 character in a sp2.98 hybrid
12. A bonding orbital for C9-O13 with 0.9989 electrons
__has 30.92% C 9 character in a sp2.31 hybrid
__has 69.08% O13 character in a sp1.48 hybrid
13. A bonding orbital for C9-O13 with 0.9986 electrons
__has 15.20% C 9 character in a p3 hybrid
__has 84.80% O13 character in a p3 hybrid
14. A bonding orbital for C12-H14 with 0.9938 electrons
__has 62.99% C12 character in a sp2.88 hybrid
__has 37.01% H14 character in a s orbital
15. A bonding orbital for C12-H15 with 0.9778 electrons
__has 63.35% C12 character in a s0.92 p3 hybrid
__has 36.65% H15 character in a s orbital
16. A bonding orbital for C12-H16 with 0.9886 electrons
__has 63.27% C12 character in a sp2.86 hybrid
__has 36.73% H16 character in a s orbital
23. A lone pair orbital for O13 with 0.9913 electrons
__made from a sp0.67 hybrid
24. A lone pair orbital for O13 with 0.9746 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 6 C 9 C12 O13 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9972 electrons
__has 47.76% C 1 character in a sp2.47 hybrid
__has 52.24% C 2 character in a sp2.23 hybrid
2. A bonding orbital for C1-H3 with 0.9954 electrons
__has 59.08% C 1 character in a s0.89 p3 hybrid
__has 40.92% H 3 character in a s orbital
3. A bonding orbital for C1-H4 with 0.9938 electrons
__has 61.42% C 1 character in a s0.95 p3 hybrid
__has 38.58% H 4 character in a s orbital
4. A bonding orbital for C1-H5 with 0.9958 electrons
__has 59.67% C 1 character in a s0.96 p3 hybrid
__has 40.33% H 5 character in a s orbital
5. A bonding orbital for C2-C6 with 0.9859 electrons
__has 46.64% C 2 character in a sp2.78 hybrid
__has 53.36% C 6 character in a sp2.17 hybrid
6. A bonding orbital for C2-H7 with 0.9791 electrons
__has 61.17% C 2 character in a s0.73 p3 hybrid
__has 38.83% H 7 character in a s orbital
7. A bonding orbital for C2-H8 with 0.9917 electrons
__has 60.71% C 2 character in a s0.90 p3 hybrid
__has 39.29% H 8 character in a s orbital
8. A bonding orbital for C6-C9 with 0.9291 electrons
__has 38.63% C 6 character in a s0.71 p3 hybrid
__has 61.37% C 9 character in a sp2.06 hybrid
9. A bonding orbital for C6-H10 with 0.9845 electrons
__has 61.56% C 6 character in a s0.97 p3 hybrid
__has 38.44% H10 character in a s orbital
10. A bonding orbital for C6-H11 with 0.9908 electrons
__has 61.72% C 6 character in a s0.98 p3 hybrid
__has 38.28% H11 character in a s orbital
11. A bonding orbital for C9-C12 with 0.9614 electrons
__has 57.34% C 9 character in a sp1.63 hybrid
__has 42.66% C12 character in a s0.92 p3 hybrid
12. A bonding orbital for C9-O13 with 0.9989 electrons
__has 34.63% C 9 character in a sp2.34 hybrid
__has 65.37% O13 character in a sp1.31 hybrid
13. A bonding orbital for C9-O13 with 0.9976 electrons
__has 23.42% C 9 character in a p3 hybrid
__has 76.58% O13 character in a p3 hybrid
14. A bonding orbital for C12-H14 with 0.9948 electrons
__has 62.39% C12 character in a sp2.79 hybrid
__has 37.61% H14 character in a s orbital
15. A bonding orbital for C12-H15 with 0.9779 electrons
__has 62.63% C12 character in a s0.94 p3 hybrid
__has 37.37% H15 character in a s orbital
16. A bonding orbital for C12-H16 with 0.9876 electrons
__has 62.83% C12 character in a sp2.80 hybrid
__has 37.17% H16 character in a s orbital
23. A lone pair orbital for O13 with 0.9903 electrons
__made from a sp0.76 hybrid
24. A lone pair orbital for O13 with 0.1154 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 6 C 9 C12 O13 -
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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-H7 with
the antibonding acceptor orbital, 172, for C6-C9 is 20.7 kJ/mol.
The interaction of bonding donor orbital, 8, for C6-C9 with
the second lone pair acceptor orbital, 24, for O13 is 105. kJ/mol.
The interaction of bonding donor orbital, 11, for C9-C12 with
the second lone pair acceptor orbital, 24, for O13 is 47.9 kJ/mol.
The interaction of bonding donor orbital, 15, for C12-H15 with
the second antibonding acceptor orbital, 177, for C9-O13 is 27.4 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.
28 ----- -3.096
27 ----- -3.116
26 ----- -3.781
25 ----- -8.388
24 -^--- -12.76
23 -^-v- -13.43
22 -^-v- -13.63
21 -^-v- -13.94
20 -^-v- -15.25
19 -^-v- -15.26
18 -^-v- -15.35
17 -^-v- -15.81
16 -^-v- -16.43
15 -^-v- -17.33
14 -^-v- -17.74
13 -^-v- -18.02
12 -^-v- -19.05
11 -^-v- -20.27
10 -^-v- -22.66
9 -^-v- -24.31
8 -^-v- -25.64
7 -^-v- -33.81
6 -^-v- -270.9
5 -^-v- -272.1
4 -^-v- -272.4
3 -^-v- -273.0
2 -^-v- -275.8
1 -^-v- -514.6
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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 = -271.5335127017 Hartrees
* The Lewis Structure (NBO analysis) calculations are done without
diffuse functions to cut down on the size of the problem.
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