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 0.9966 electrons
__has 50.73% C 1 character in a sp1.84 hybrid
__has 49.27% C 2 character in a sp2.39 hybrid
2. A bonding orbital for C1-C6 with 0.9960 electrons
__has 49.85% C 1 character in a sp2.03 hybrid
__has 50.15% C 6 character in a sp2.31 hybrid
3. A bonding orbital for C1-H10 with 0.9921 electrons
__has 61.12% C 1 character in a sp2.30 hybrid
__has 38.88% H10 character in a s orbital
4. A bonding orbital for C2-H3 with 0.9964 electrons
__has 58.56% C 2 character in a s0.94 p3 hybrid
__has 41.44% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9964 electrons
__has 59.28% C 2 character in a s0.95 p3 hybrid
__has 40.72% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 0.9984 electrons
__has 57.09% C 2 character in a s0.89 p3 hybrid
__has 42.91% H 5 character in a s orbital
7. A bonding orbital for C6-O7 with 0.9978 electrons
__has 33.59% C 6 character in a s0.91 p3 hybrid
__has 66.41% O 7 character in a sp2.54 hybrid
8. A bonding orbital for C6-H9 with 0.9957 electrons
__has 56.61% C 6 character in a s0.95 p3 hybrid
__has 43.39% H 9 character in a s orbital
9. A bonding orbital for C6-H11 with 0.9970 electrons
__has 55.29% C 6 character in a s0.89 p3 hybrid
__has 44.71% H11 character in a s orbital
10. A bonding orbital for O7-H8 with 0.9953 electrons
__has 73.15% O 7 character in a s0.79 p3 hybrid
__has 26.85% H 8 character in a s orbital
15. A lone pair orbital for C1 with 0.9466 electrons
__made from a s0.05 p3 hybrid
16. A lone pair orbital for O7 with 0.9940 electrons
__made from a sp0.96 hybrid
17. A lone pair orbital for O7 with 0.9850 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 6 O 7 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9969 electrons
__has 45.71% C 1 character in a sp1.82 hybrid
__has 54.29% C 2 character in a sp2.27 hybrid
2. A bonding orbital for C1-C6 with 0.9961 electrons
__has 45.04% C 1 character in a sp1.99 hybrid
__has 54.96% C 6 character in a sp2.20 hybrid
3. A bonding orbital for C1-H10 with 0.9932 electrons
__has 55.65% C 1 character in a sp2.23 hybrid
__has 44.35% H10 character in a s orbital
4. A bonding orbital for C2-H3 with 0.9932 electrons
__has 60.26% C 2 character in a s0.91 p3 hybrid
__has 39.74% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9939 electrons
__has 60.50% C 2 character in a s0.92 p3 hybrid
__has 39.50% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 0.9847 electrons
__has 61.78% C 2 character in a s0.89 p3 hybrid
__has 38.22% H 5 character in a s orbital
7. A bonding orbital for C6-O7 with 0.9977 electrons
__has 34.31% C 6 character in a s0.88 p3 hybrid
__has 65.69% O 7 character in a sp2.59 hybrid
8. A bonding orbital for C6-H9 with 0.9909 electrons
__has 58.66% C 6 character in a s0.91 p3 hybrid
__has 41.34% H 9 character in a s orbital
9. A bonding orbital for C6-H11 with 0.9848 electrons
__has 59.58% C 6 character in a s0.89 p3 hybrid
__has 40.42% H11 character in a s orbital
10. A bonding orbital for O7-H8 with 0.9958 electrons
__has 73.10% O 7 character in a s0.79 p3 hybrid
__has 26.90% H 8 character in a s orbital
16. A lone pair orbital for O7 with 0.9945 electrons
__made from a sp0.95 hybrid
17. A lone pair orbital for O7 with 0.9861 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 6 O 7 -
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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-H5 with
the lone pair acceptor orbital, 15, for C1 is 27.9 kJ/mol.
The interaction of bonding donor orbital, 9, for C6-H11 with
the lone pair acceptor orbital, 15, for C1 is 27.5 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.
21 ----- 2.376
20 ----- 2.167
19 ----- 1.571
18 ----- 0.567
17 -^--- -4.094
16 -^-v- -6.344
15 -^-v- -8.026
14 -^-v- -8.865
13 -^-v- -9.471
12 -^-v- -9.812
11 -^-v- -10.69
10 -^-v- -11.30
9 -^-v- -12.69
8 -^-v- -13.93
7 -^-v- -16.80
6 -^-v- -19.20
5 -^-v- -25.09
4 -^-v- -266.2
3 -^-v- -266.5
2 -^-v- -267.6
1 -^-v- -506.3
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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 = -193.7536727675 Hartrees
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