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.
Please note that your structure can't be well described by a single
Lewis structure, because of extensive delocalization.
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 0.9988 electrons
__has 65.22% O 1 character in a sp2.01 hybrid
__has 34.78% C 2 character in a sp2.24 hybrid
2. A bonding orbital for C2-O3 with 0.9988 electrons
__has 34.78% C 2 character in a sp2.24 hybrid
__has 65.22% O 3 character in a sp2.01 hybrid
3. A bonding orbital for C2-C4 with 0.9985 electrons
__has 48.52% C 2 character in a sp1.58 hybrid
__has 51.48% C 4 character in a sp2.84 hybrid
4. A bonding orbital for C4-H5 with 0.9871 electrons
__has 62.37% C 4 character in a s0.96 p3 hybrid
__has 37.63% H 5 character in a s orbital
5. A bonding orbital for C4-H6 with 0.9931 electrons
__has 62.29% C 4 character in a s0.99 p3 hybrid
__has 37.71% H 6 character in a s orbital
6. A bonding orbital for C4-H7 with 0.9931 electrons
__has 62.29% C 4 character in a s0.99 p3 hybrid
__has 37.71% H 7 character in a s orbital
11. A lone pair orbital for O1 with 0.9918 electrons
__made from a sp0.49 hybrid
12. A lone pair orbital for O1 with 0.9727 electrons
__made from a p3 hybrid
13. A lone pair orbital for O1 with 0.8669 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)
14. A lone pair orbital for C2 with 0.2774 electrons
__made from a p-pi orbital ( 99.82% p 0.18% d)
15. A lone pair orbital for O3 with 0.9918 electrons
__made from a sp0.49 hybrid
16. A lone pair orbital for O3 with 0.9727 electrons
__made from a p3 hybrid
17. A lone pair orbital for O3 with 0.8668 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)
-With core pairs on: O 1 C 2 O 3 C 4 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9613 electrons
__has 59.65% O 1 character in a sp2.03 hybrid
__has 40.35% C 2 character in a sp2.68 hybrid
2. A antibonding orbital for O1-O3 with 0.9336 electrons
__has 50.01% O 1 character in a s0.14 p3 hybrid
__has 49.99% O 3 character in a s0.14 p3 hybrid
3. A bonding orbital for C2-O3 with 0.9613 electrons
__has 40.34% C 2 character in a sp2.68 hybrid
__has 59.66% O 3 character in a sp2.03 hybrid
4. A bonding orbital for C2-C4 with 0.9282 electrons
__has 58.23% C 2 character in a sp1.17 hybrid
__has 41.77% C 4 character in a s0.97 p3 hybrid
5. A bonding orbital for C4-H5 with 0.9848 electrons
__has 61.42% C 4 character in a s0.98 p3 hybrid
__has 38.58% H 5 character in a s orbital
6. A bonding orbital for C4-H6 with 0.9918 electrons
__has 61.13% C 4 character in a sp2.92 hybrid
__has 38.87% H 6 character in a s orbital
7. A bonding orbital for C4-H7 with 0.9918 electrons
__has 61.13% C 4 character in a sp2.92 hybrid
__has 38.87% H 7 character in a s orbital
12. A lone pair orbital for O1 with 0.9903 electrons
__made from a sp0.59 hybrid
13. A lone pair orbital for O1 with 0.8390 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)
14. A lone pair orbital for C2 with 0.3298 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)
15. A lone pair orbital for O3 with 0.9903 electrons
__made from a sp0.59 hybrid
16. A lone pair orbital for O3 with 0.8390 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)
109. A bonding orbital for O1-O3 with 0.1466 electrons
__has 49.99% O 1 character in a s0.14 p3 hybrid
__has 50.01% O 3 character in a s0.14 p3 hybrid
-With core pairs on: O 1 C 2 O 3 C 4 -
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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, 1, for O1-C2 with
the bonding acceptor orbital, 109, for O1-O3 is 110. kJ/mol.
The interaction of antibonding donor orbital, 2, for O1-O3 with
the antibonding acceptor orbital, 108, for O1-C2 is 51.8 kJ/mol.
The interaction of antibonding donor orbital, 2, for O1-O3 with
the antibonding acceptor orbital, 110, for C2-O3 is 51.7 kJ/mol.
The interaction of bonding donor orbital, 3, for C2-O3 with
the bonding acceptor orbital, 109, for O1-O3 is 110. kJ/mol.
The interaction of bonding donor orbital, 4, for C2-C4 with
the bonding acceptor orbital, 109, for O1-O3 is 62.9 kJ/mol.
The interaction of bonding donor orbital, 5, for C4-H5 with
the lone pair acceptor orbital, 14, for C2 is 20.5 kJ/mol.
The interaction of the second lone pair donor orbital, 13, for O1 with
the lone pair acceptor orbital, 14, for C2 is 457. kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O3 with
the lone pair acceptor orbital, 14, for C2 is 457. 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.
20 ----- 2.707
19 ----- 2.101
18 ----- 1.385
17 ----- -1.922
16 -^--- -7.978
15 -^-v- -8.208
14 -^-v- -8.635
13 -^-v- -10.26
12 -^-v- -10.62
11 -^-v- -12.24
10 -^-v- -12.30
9 -^-v- -12.70
8 -^-v- -13.92
7 -^-v- -19.26
6 -^-v- -25.33
5 -^-v- -28.28
4 -^-v- -267.3
3 -^-v- -270.5
2 -^-v- -508.2 1 -^-v- -508.2
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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 = -228.5089228629 Hartrees
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