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 0.9968 electrons
__has 73.64% O 1 character in a sp2.03 hybrid
__has 26.36% C 2 character in a s0.74 p3 hybrid
2. A bonding orbital for O1-C9 with 0.9973 electrons
__has 73.49% O 1 character in a sp2.18 hybrid
__has 26.51% C 9 character in a s0.77 p3 hybrid
3. A bonding orbital for C2-C3 with 0.9985 electrons
__has 53.07% C 2 character in a sp1.81 hybrid
__has 46.93% C 3 character in a sp2.67 hybrid
4. A bonding orbital for C2-H7 with 0.9935 electrons
__has 60.29% C 2 character in a s0.87 p3 hybrid
__has 39.71% H 7 character in a s orbital
5. A bonding orbital for C2-H8 with 0.9935 electrons
__has 60.30% C 2 character in a s0.87 p3 hybrid
__has 39.70% H 8 character in a s orbital
6. A bonding orbital for C3-H4 with 0.9943 electrons
__has 60.94% C 3 character in a s0.96 p3 hybrid
__has 39.06% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9876 electrons
__has 62.56% C 3 character in a s0.97 p3 hybrid
__has 37.44% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 0.9943 electrons
__has 60.92% C 3 character in a s0.96 p3 hybrid
__has 39.08% H 6 character in a s orbital
9. A bonding orbital for C9-H10 with 0.9974 electrons
__has 60.57% C 9 character in a sp2.97 hybrid
__has 39.43% H10 character in a s orbital
10. A bonding orbital for C9-H11 with 0.9973 electrons
__has 60.66% C 9 character in a sp2.94 hybrid
__has 39.34% H11 character in a s orbital
11. A bonding orbital for C9-H12 with 0.9977 electrons
__has 61.28% C 9 character in a sp2.41 hybrid
__has 38.72% H12 character in a s orbital
16. A lone pair orbital for O1 with 0.9892 electrons
__made from a sp1.80 hybrid
17. A lone pair orbital for O1 with 0.9869 electrons
__made from a p-pi orbital ( 99.97% p)
-With core pairs on: O 1 C 2 C 3 C 9 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9970 electrons
__has 69.01% O 1 character in a sp1.96 hybrid
__has 30.99% C 2 character in a s0.76 p3 hybrid
2. A bonding orbital for O1-C9 with 0.9976 electrons
__has 68.82% O 1 character in a sp2.10 hybrid
__has 31.18% C 9 character in a s0.80 p3 hybrid
3. A bonding orbital for C2-C3 with 0.9984 electrons
__has 53.14% C 2 character in a sp1.83 hybrid
__has 46.86% C 3 character in a sp2.67 hybrid
4. A bonding orbital for C2-H7 with 0.9545 electrons
__has 64.51% C 2 character in a s0.86 p3 hybrid
__has 35.49% H 7 character in a s orbital
5. A bonding orbital for C2-H8 with 0.9546 electrons
__has 64.51% C 2 character in a s0.86 p3 hybrid
__has 35.49% H 8 character in a s orbital
6. A bonding orbital for C3-H4 with 0.9943 electrons
__has 61.02% C 3 character in a s0.96 p3 hybrid
__has 38.98% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9888 electrons
__has 62.41% C 3 character in a s0.96 p3 hybrid
__has 37.59% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 0.9943 electrons
__has 61.00% C 3 character in a s0.96 p3 hybrid
__has 39.00% H 6 character in a s orbital
9. A bonding orbital for C9-H10 with 0.9669 electrons
__has 64.23% C 9 character in a sp2.99 hybrid
__has 35.77% H10 character in a s orbital
10. A bonding orbital for C9-H11 with 0.9685 electrons
__has 64.12% C 9 character in a sp2.97 hybrid
__has 35.88% H11 character in a s orbital
11. A bonding orbital for C9-H12 with 0.9977 electrons
__has 61.41% C 9 character in a sp2.44 hybrid
__has 38.59% H12 character in a s orbital
16. A lone pair orbital for O1 with 0.9872 electrons
__made from a sp1.92 hybrid
17. A lone pair orbital for O1 with 0.1378 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)
-With core pairs on: O 1 C 2 C 3 C 9 -
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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, 4, for C2-H7 with
the second lone pair acceptor orbital, 17, for O1 is 52.5 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H8 with
the second lone pair acceptor orbital, 17, for O1 is 52.3 kJ/mol.
The interaction of bonding donor orbital, 7, for C3-H5 with
the antibonding acceptor orbital, 134, for O1-C2 is 20.2 kJ/mol.
The interaction of bonding donor orbital, 9, for C9-H10 with
the second lone pair acceptor orbital, 17, for O1 is 42.5 kJ/mol.
The interaction of bonding donor orbital, 10, for C9-H11 with
the second lone pair acceptor orbital, 17, for O1 is 39.8 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 ----- -2.928
20 ----- -3.339
19 ----- -3.576
18 ----- -5.024
17 -^--- -13.24
16 -^-v- -14.55
15 -^-v- -14.83
14 -^-v- -14.93
13 -^-v- -15.90
12 -^-v- -16.58
11 -^-v- -18.03
10 -^-v- -18.86
9 -^-v- -19.10
8 -^-v- -20.86
7 -^-v- -23.60
6 -^-v- -25.59
5 -^-v- -33.79
4 -^-v- -271.8
3 -^-v- -273.9
2 -^-v- -274.5
1 -^-v- -515.6
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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 = -194.0645897745 Hartrees
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