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 0.9962 electrons
__has 48.41% C 1 character in a sp2.33 hybrid
__has 51.59% C 2 character in a sp2.13 hybrid
2. A bonding orbital for C1-H6 with 0.9894 electrons
__has 61.11% C 1 character in a s0.82 p3 hybrid
__has 38.89% H 6 character in a s orbital
3. A bonding orbital for C1-H7 with 0.9948 electrons
__has 60.88% C 1 character in a s0.96 p3 hybrid
__has 39.12% H 7 character in a s orbital
4. A bonding orbital for C1-H8 with 0.9941 electrons
__has 61.10% C 1 character in a s0.96 p3 hybrid
__has 38.90% H 8 character in a s orbital
5. A bonding orbital for C2-C3 with 0.9959 electrons
__has 51.67% C 2 character in a sp2.15 hybrid
__has 48.33% C 3 character in a sp2.34 hybrid
6. A bonding orbital for C2-C4 with 0.9852 electrons
__has 48.56% C 2 character in a s0.41 p3 hybrid
__has 51.44% C 4 character in a s0.63 p3 hybrid
7. A bonding orbital for C2-H9 with 0.9892 electrons
__has 61.68% C 2 character in a s0.97 p3 hybrid
__has 38.32% H 9 character in a s orbital
8. A bonding orbital for C3-H10 with 0.9896 electrons
__has 61.00% C 3 character in a s0.81 p3 hybrid
__has 39.00% H10 character in a s orbital
9. A bonding orbital for C3-H11 with 0.9948 electrons
__has 61.09% C 3 character in a s0.97 p3 hybrid
__has 38.91% H11 character in a s orbital
10. A bonding orbital for C3-H12 with 0.9940 electrons
__has 61.23% C 3 character in a s0.97 p3 hybrid
__has 38.77% H12 character in a s orbital
11. A bonding orbital for C4-O5 with 0.9984 electrons
__has 32.47% C 4 character in a sp2.74 hybrid
__has 67.53% O 5 character in a sp1.96 hybrid
12. A bonding orbital for C4-H13 with 0.9946 electrons
__has 60.88% C 4 character in a sp2.55 hybrid
__has 39.12% H13 character in a s orbital
13. A bonding orbital for C4-H14 with 0.9966 electrons
__has 60.04% C 4 character in a sp2.53 hybrid
__has 39.96% H14 character in a s orbital
14. A bonding orbital for O5-H15 with 0.9943 electrons
__has 76.67% O 5 character in a s0.82 p3 hybrid
__has 23.33% H15 character in a s orbital
20. A lone pair orbital for O5 with 0.9913 electrons
__made from a sp1.25 hybrid
21. A lone pair orbital for O5 with 0.9716 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 3 C 4 O 5 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9934 electrons
__has 49.26% C 1 character in a sp2.34 hybrid
__has 50.74% C 2 character in a sp1.85 hybrid
2. A bonding orbital for C1-H6 with 0.9619 electrons
__has 63.72% C 1 character in a s0.86 p3 hybrid
__has 36.28% H 6 character in a s orbital
3. A bonding orbital for C1-H7 with 0.9924 electrons
__has 61.35% C 1 character in a s0.93 p3 hybrid
__has 38.65% H 7 character in a s orbital
4. A bonding orbital for C1-H8 with 0.9932 electrons
__has 61.39% C 1 character in a s0.94 p3 hybrid
__has 38.61% H 8 character in a s orbital
5. A bonding orbital for C2-C3 with 0.9923 electrons
__has 51.05% C 2 character in a sp1.84 hybrid
__has 48.95% C 3 character in a sp2.36 hybrid
6. A bonding orbital for C2-H9 with 0.9835 electrons
__has 61.30% C 2 character in a sp2.40 hybrid
__has 38.70% H 9 character in a s orbital
7. A bonding orbital for C3-H10 with 0.9603 electrons
__has 63.67% C 3 character in a s0.86 p3 hybrid
__has 36.33% H10 character in a s orbital
8. A bonding orbital for C3-H11 with 0.9935 electrons
__has 61.38% C 3 character in a s0.94 p3 hybrid
__has 38.62% H11 character in a s orbital
9. A bonding orbital for C3-H12 with 0.9923 electrons
__has 61.54% C 3 character in a s0.94 p3 hybrid
__has 38.46% H12 character in a s orbital
10. A bonding orbital for C4-O5 with 0.9950 electrons
__has 31.46% C 4 character in a s0.98 p3 hybrid
__has 68.54% O 5 character in a sp1.88 hybrid
11. A bonding orbital for C4-O5 with 0.9721 electrons
__has 19.66% C 4 character in a s0.15 p3 hybrid
__has 80.34% O 5 character in a p3 hybrid
12. A bonding orbital for C4-H13 with 0.9820 electrons
__has 61.53% C 4 character in a sp1.82 hybrid
__has 38.47% H13 character in a s orbital
13. A bonding orbital for C4-H14 with 0.9844 electrons
__has 60.93% C 4 character in a sp1.83 hybrid
__has 39.07% H14 character in a s orbital
14. A bonding orbital for O5-H15 with 0.9943 electrons
__has 75.62% O 5 character in a s0.84 p3 hybrid
__has 24.38% H15 character in a s orbital
20. A lone pair orbital for C2 with 0.1255 electrons
__made from a p3 hybrid
21. A lone pair orbital for O5 with 0.9907 electrons
__made from a sp1.32 hybrid
-With core pairs on: C 1 C 2 C 3 C 4 O 5 -
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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, 2, for C1-H6 with
the lone pair acceptor orbital, 20, for C2 is 62.5 kJ/mol.
The interaction of bonding donor orbital, 7, for C3-H10 with
the lone pair acceptor orbital, 20, for C2 is 64.2 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the second antibonding acceptor orbital, 177, for C4-O5 is 15.3 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C3 with
the antibonding acceptor orbital, 176, for C4-O5 is 2.34 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C3 with
the second antibonding acceptor orbital, 177, for C4-O5 is 12.7 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H9 with
the second antibonding acceptor orbital, 177, for C4-O5 is 26.4 kJ/mol.
The interaction of lone pair donor orbital, 20, for C2 with
the second antibonding acceptor orbital, 177, for C4-O5 is 159. kJ/mol.
The interaction of bonding donor orbital, 10, for C4-O5 with
the lone pair acceptor orbital, 20, for C2 is 3.51 kJ/mol.
The interaction of the second bonding donor orbital, 11, for C4-O5 with
the lone pair acceptor orbital, 20, for C2 is 51.7 kJ/mol.
The interaction of bonding donor orbital, 12, for C4-H13 with
the lone pair acceptor orbital, 20, for C2 is 48.8 kJ/mol.
The interaction of bonding donor orbital, 12, for C4-H13 with
the antibonding acceptor orbital, 172, for C2-H9 is 2.05 kJ/mol.
The interaction of bonding donor orbital, 13, for C4-H14 with
the lone pair acceptor orbital, 20, for C2 is 47.9 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 ----- -2.973
24 ----- -3.599
23 ----- -5.027
22 ----- -5.528
21 -^--- -12.03
20 -^-v- -13.81
19 -^-v- -14.03
18 -^-v- -14.43
17 -^-v- -14.50
16 -^-v- -15.00
15 -^-v- -15.43
14 -^-v- -16.61
13 -^-v- -16.89
12 -^-v- -17.59
11 -^-v- -19.44
10 -^-v- -19.78
9 -^-v- -22.30
8 -^-v- -22.98
7 -^-v- -25.45
6 -^-v- -33.03
5 -^-v- -271.3
4 -^-v- -271.4
3 -^-v- -273.4
2 -^-v- -274.6
1 -^-v- -514.1
Top of page.
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 = -233.4058906672 Hartrees
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