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.
Hybridization in the Best Lewis Structure
1. A bonding orbital for O1-C2 with 1.9954 electrons
__has 67.73% O 1 character in a sp2.28 hybrid
__has 32.27% C 2 character in a sp2.58 hybrid
2. A bonding orbital for O1-H11 with 1.9888 electrons
__has 75.07% O 1 character in a s0.85 p3 hybrid
__has 24.93% H11 character in a s orbital
3. A bonding orbital for C2-O3 with 1.9976 electrons
__has 35.47% C 2 character in a sp1.87 hybrid
__has 64.53% O 3 character in a sp1.56 hybrid
4. A bonding orbital for C2-O3 with 1.9940 electrons
__has 26.07% C 2 character in a p3 hybrid
__has 73.93% O 3 character in a p3 hybrid
5. A bonding orbital for C2-C4 with 1.9870 electrons
__has 49.47% C 2 character in a sp1.64 hybrid
__has 50.53% C 4 character in a s0.96 p3 hybrid
6. A bonding orbital for C4-C5 with 1.9914 electrons
__has 52.16% C 4 character in a sp2.30 hybrid
__has 47.84% C 5 character in a sp2.55 hybrid
7. A bonding orbital for C4-H9 with 1.9710 electrons
__has 60.48% C 4 character in a s0.87 p3 hybrid
__has 39.52% H 9 character in a s orbital
8. A bonding orbital for C4-H10 with 1.9767 electrons
__has 60.55% C 4 character in a s0.90 p3 hybrid
__has 39.45% H10 character in a s orbital
9. A bonding orbital for C5-H6 with 1.9920 electrons
__has 59.61% C 5 character in a s0.94 p3 hybrid
__has 40.39% H 6 character in a s orbital
10. A bonding orbital for C5-H7 with 1.9918 electrons
__has 60.07% C 5 character in a s0.95 p3 hybrid
__has 39.93% H 7 character in a s orbital
11. A bonding orbital for C5-H8 with 1.9909 electrons
__has 59.30% C 5 character in a s0.94 p3 hybrid
__has 40.70% H 8 character in a s orbital
17. A lone pair orbital for O1 with 1.9813 electrons
__made from a sp1.10 hybrid
18. A lone pair orbital for O1 with 1.8836 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)
19. A lone pair orbital for O3 with 1.9772 electrons
__made from a sp0.63 hybrid
20. A lone pair orbital for O3 with 1.8856 electrons
__made from a p3 hybrid
149. A antibonding orbital for C2-O3 with 0.1407 electrons
__has 73.93% C 2 character in a p3 hybrid
__has 26.07% O 3 character in a p3 hybrid
-With core pairs on: O 1 C 2 O 3 C 4 C 5 -
Top of page.
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 O1-H11 with
the antibonding acceptor orbital, 150, for C2-C4 is 22.7 kJ/mol.
The interaction of bonding donor orbital, 7, for C4-H9 with
the second antibonding acceptor orbital, 149, for C2-O3 is 31.9 kJ/mol.
The interaction of bonding donor orbital, 8, for C4-H10 with
the second antibonding acceptor orbital, 149, for C2-O3 is 21.7 kJ/mol.
The interaction of lone pair donor orbital, 17, for O1 with
the antibonding acceptor orbital, 148, for C2-O3 is 39.9 kJ/mol.
The interaction of the second lone pair donor orbital, 18, for O1 with
the second antibonding acceptor orbital, 149, for C2-O3 is 228. kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O3 with
the antibonding acceptor orbital, 146, for O1-C2 is 179. kJ/mol.
The interaction of the second lone pair donor orbital, 20, for O3 with
the antibonding acceptor orbital, 150, for C2-C4 is 101. 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.
24 ----- 1.931
23 ----- 1.526
22 ----- 0.747
21 ----- -1.385
20 -^-v- -6.680
19 -^-v- -7.959
18 -^-v- -8.528
17 -^-v- -8.955
16 -^-v- -9.504
15 -^-v- -10.03
14 -^-v- -10.28
13 -^-v- -11.72
12 -^-v- -11.92
11 -^-v- -12.34
10 -^-v- -14.47
9 -^-v- -16.70
8 -^-v- -19.51
7 -^-v- -25.25
6 -^-v- -27.55
5 -^-v- -266.2
4 -^-v- -266.9
3 -^-v- -270.0
2 -^-v- -506.4
1 -^-v- -507.8
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 = -268.5028889484 Hartrees
Top of page.
-> Return to Molecular Structure Page.
-> Return to Chemistry Home Page