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.
Hybridization in the Best Lewis Structure
1. A bonding orbital for C1-C2 with 1.9901 electrons
__has 49.24% C 1 character in a sp2.45 hybrid
__has 50.76% C 2 character in a sp2.69 hybrid
2. A bonding orbital for C1-H6 with 1.9925 electrons
__has 59.52% C 1 character in a s0.94 p3 hybrid
__has 40.48% H 6 character in a s orbital
3. A bonding orbital for C1-H7 with 1.9925 electrons
__has 58.91% C 1 character in a s0.92 p3 hybrid
__has 41.09% H 7 character in a s orbital
4. A bonding orbital for C1-H8 with 1.9923 electrons
__has 59.03% C 1 character in a s0.93 p3 hybrid
__has 40.97% H 8 character in a s orbital
5. A bonding orbital for C2-C3 with 1.9874 electrons
__has 51.07% C 2 character in a sp2.70 hybrid
__has 48.93% C 3 character in a sp2.47 hybrid
6. A bonding orbital for C2-C4 with 1.9889 electrons
__has 50.95% C 2 character in a sp2.94 hybrid
__has 49.05% C 4 character in a sp2.34 hybrid
7. A bonding orbital for C2-H9 with 1.9755 electrons
__has 58.92% C 2 character in a s0.79 p3 hybrid
__has 41.08% H 9 character in a s orbital
8. A bonding orbital for C3-H10 with 1.9924 electrons
__has 59.39% C 3 character in a s0.94 p3 hybrid
__has 40.61% H10 character in a s orbital
9. A bonding orbital for C3-H11 with 1.9924 electrons
__has 58.98% C 3 character in a s0.92 p3 hybrid
__has 41.02% H11 character in a s orbital
10. A bonding orbital for C3-H12 with 1.9923 electrons
__has 59.29% C 3 character in a s0.94 p3 hybrid
__has 40.71% H12 character in a s orbital
11. A bonding orbital for C4-O5 with 1.9957 electrons
__has 33.47% C 4 character in a s0.88 p3 hybrid
__has 66.53% O 5 character in a sp2.45 hybrid
12. A bonding orbital for C4-H13 with 1.9870 electrons
__has 58.24% C 4 character in a s0.94 p3 hybrid
__has 41.76% H13 character in a s orbital
13. A bonding orbital for C4-H14 with 1.9907 electrons
__has 57.11% C 4 character in a s0.93 p3 hybrid
__has 42.89% H14 character in a s orbital
14. A bonding orbital for O5-H15 with 1.9905 electrons
__has 73.01% O 5 character in a s0.78 p3 hybrid
__has 26.99% H15 character in a s orbital
20. A lone pair orbital for O5 with 1.9861 electrons
__made from a sp0.98 hybrid
21. A lone pair orbital for O5 with 1.9692 electrons
__made from a p3 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 the second lone pair donor orbital, 21, for O5 with
the antibonding acceptor orbital, 172, for C2-C4 is 35.5 kJ/mol.
The interaction of the second lone pair donor orbital, 21, for O5 with
the antibonding acceptor orbital, 179, for C4-H14 is 26.9 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.
25 ----- 2.061
24 ----- 1.886
23 ----- 1.322
22 ----- 0.524
21 -^-v- -6.233
20 -^-v- -7.599
19 -^-v- -8.046
18 -^-v- -8.300
17 -^-v- -8.934
16 -^-v- -9.205
15 -^-v- -9.496
14 -^-v- -10.48
13 -^-v- -10.90
12 -^-v- -11.16
11 -^-v- -12.64
10 -^-v- -13.89
9 -^-v- -16.46
8 -^-v- -16.88
7 -^-v- -19.71
6 -^-v- -25.08
5 -^-v- -266.1
4 -^-v- -266.1
3 -^-v- -266.5
2 -^-v- -267.4
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 = -233.7449754484 Hartrees
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