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 H1-C2 with 0.9935 electrons
__has 38.47% H 1 character in a s orbital
__has 61.53% C 2 character in a s0.98 p3 hybrid
2. A bonding orbital for C2-C3 with 0.9929 electrons
__has 46.21% C 2 character in a sp2.55 hybrid
__has 53.79% C 3 character in a sp2.14 hybrid
3. A bonding orbital for C2-H7 with 0.9955 electrons
__has 60.05% C 2 character in a s0.92 p3 hybrid
__has 39.95% H 7 character in a s orbital
4. A bonding orbital for C2-H8 with 0.9955 electrons
__has 60.06% C 2 character in a s0.93 p3 hybrid
__has 39.94% H 8 character in a s orbital
5. A bonding orbital for C3-C4 with 0.9966 electrons
__has 45.91% C 3 character in a sp2.78 hybrid
__has 54.09% C 4 character in a sp1.81 hybrid
6. A bonding orbital for C3-H9 with 0.9890 electrons
__has 60.83% C 3 character in a s0.79 p3 hybrid
__has 39.17% H 9 character in a s orbital
7. A bonding orbital for C3-H10 with 0.9892 electrons
__has 60.93% C 3 character in a s0.80 p3 hybrid
__has 39.07% H10 character in a s orbital
8. A bonding orbital for C4-O5 with 0.9985 electrons
__has 27.22% C 4 character in a s0.80 p3 hybrid
__has 72.78% O 5 character in a sp1.86 hybrid
9. A bonding orbital for C4-H11 with 0.9949 electrons
__has 59.70% C 4 character in a s0.85 p3 hybrid
__has 40.30% H11 character in a s orbital
10. A bonding orbital for C4-H12 with 0.9949 electrons
__has 59.53% C 4 character in a s0.83 p3 hybrid
__has 40.47% H12 character in a s orbital
11. A bonding orbital for O5-H6 with 0.9956 electrons
__has 78.77% O 5 character in a s0.77 p3 hybrid
__has 21.23% H 6 character in a s orbital
16. A lone pair orbital for O5 with 0.9952 electrons
__made from a sp1.23 hybrid
17. A lone pair orbital for O5 with 0.9909 electrons
__made from a p-pi orbital ( 99.95% p)
-With core pairs on: C 2 C 3 C 4 O 5 -
Up Electrons
1. A bonding orbital for H1-C2 with 0.9937 electrons
__has 38.50% H 1 character in a s orbital
__has 61.50% C 2 character in a s0.98 p3 hybrid
2. A bonding orbital for C2-C3 with 0.9935 electrons
__has 46.33% C 2 character in a sp2.54 hybrid
__has 53.67% C 3 character in a sp2.14 hybrid
3. A bonding orbital for C2-H7 with 0.9954 electrons
__has 60.04% C 2 character in a s0.92 p3 hybrid
__has 39.96% H 7 character in a s orbital
4. A bonding orbital for C2-H8 with 0.9954 electrons
__has 60.05% C 2 character in a s0.93 p3 hybrid
__has 39.95% H 8 character in a s orbital
5. A bonding orbital for C3-C4 with 0.9963 electrons
__has 45.77% C 3 character in a sp2.78 hybrid
__has 54.23% C 4 character in a sp1.83 hybrid
6. A bonding orbital for C3-H9 with 0.9893 electrons
__has 60.93% C 3 character in a s0.79 p3 hybrid
__has 39.07% H 9 character in a s orbital
7. A bonding orbital for C3-H10 with 0.9896 electrons
__has 61.01% C 3 character in a s0.80 p3 hybrid
__has 38.99% H10 character in a s orbital
8. A bonding orbital for C4-O5 with 0.9983 electrons
__has 31.55% C 4 character in a s0.81 p3 hybrid
__has 68.45% O 5 character in a sp1.77 hybrid
9. A bonding orbital for C4-H11 with 0.9386 electrons
__has 65.69% C 4 character in a s0.85 p3 hybrid
__has 34.31% H11 character in a s orbital
10. A bonding orbital for C4-H12 with 0.9334 electrons
__has 66.02% C 4 character in a s0.83 p3 hybrid
__has 33.98% H12 character in a s orbital
11. A bonding orbital for O5-H6 with 0.9957 electrons
__has 74.93% O 5 character in a s0.84 p3 hybrid
__has 25.07% H 6 character in a s orbital
16. A lone pair orbital for O5 with 0.9945 electrons
__made from a sp1.37 hybrid
17. A lone pair orbital for O5 with 0.1200 electrons
__made from a p-pi orbital ( 99.78% p 0.22% d)
-With core pairs on: 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, 9, for C4-H11 with
the second lone pair acceptor orbital, 17, for O5 is 66.8 kJ/mol.
The interaction of bonding donor orbital, 10, for C4-H12 with
the second lone pair acceptor orbital, 17, for O5 is 74.7 kJ/mol.
Top of page.
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 ----- -3.168
20 ----- -3.408
19 ----- -3.881
18 ----- -5.482
17 -^--- -13.45
16 -^-v- -13.96
15 -^-v- -14.02
14 -^-v- -14.99
13 -^-v- -15.37
12 -^-v- -15.98
11 -^-v- -17.36
10 -^-v- -18.47
9 -^-v- -20.16
8 -^-v- -20.80
7 -^-v- -22.96
6 -^-v- -25.69
5 -^-v- -33.33
4 -^-v- -271.3
3 -^-v- -272.6
2 -^-v- -274.8
1 -^-v- -514.8
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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 = -194.0574595907 Hartrees
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