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 C1-C2 with 1.9923 electrons
__has 61.28% C 1 character in a sp1.07 hybrid
__has 38.72% C 2 character in a sp2.22 hybrid
2. A bonding orbital for C1-C2 with 1.8273 electrons
__has 66.60% C 1 character in a p-pi orbital ( 99.97% p)
__has 33.40% C 2 character in a p-pi orbital ( 99.56% p 0.44% d)
3. A bonding orbital for C1-C3 with 1.9124 electrons
__has 61.68% C 1 character in a sp2.49 hybrid
__has 38.32% C 3 character in a s0.68 p3 hybrid
4. A bonding orbital for C1-C4 with 1.8659 electrons
__has 50.00% C 1 character in a s0.91 p3 hybrid
__has 50.00% C 4 character in a s0.91 p3 hybrid
5. A bonding orbital for C3-C4 with 1.9123 electrons
__has 38.31% C 3 character in a s0.68 p3 hybrid
__has 61.69% C 4 character in a sp2.49 hybrid
6. A bonding orbital for C4-C5 with 1.9923 electrons
__has 61.28% C 4 character in a sp1.07 hybrid
__has 38.72% C 5 character in a sp2.22 hybrid
7. A bonding orbital for C4-C5 with 1.8273 electrons
__has 66.59% C 4 character in a p-pi orbital ( 99.97% p)
__has 33.41% C 5 character in a p-pi orbital ( 99.56% p 0.44% d)
13. A lone pair orbital for C2 with 1.9749 electrons
__made from a sp0.44 hybrid
14. A lone pair orbital for C2 with 0.1225 electrons
__made from a p3 hybrid
15. A lone pair orbital for C3 with 1.9544 electrons
__made from a sp0.57 hybrid
16. A lone pair orbital for C3 with 0.2200 electrons
__made from a p-pi orbital ( 99.19% p 0.81% d)
17. A lone pair orbital for C5 with 1.9749 electrons
__made from a sp0.44 hybrid
18. A lone pair orbital for C5 with 0.1225 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 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, 1, for C1-C2 with
the antibonding acceptor orbital, 116, for C1-C3 is 20.0 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the antibonding acceptor orbital, 117, for C1-C4 is 22.6 kJ/mol.
The interaction of the second bonding donor orbital, 2, for C1-C2 with
the second lone pair acceptor orbital, 16, for C3 is 186. kJ/mol.
The interaction of the second bonding donor orbital, 2, for C1-C2 with
the second antibonding acceptor orbital, 120, for C4-C5 is 60.7 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the second lone pair acceptor orbital, 14, for C2 is 51.7 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the antibonding acceptor orbital, 117, for C1-C4 is 26.1 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the antibonding acceptor orbital, 119, for C4-C5 is 97.4 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C4 with
the second lone pair acceptor orbital, 14, for C2 is 49.5 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C4 with
the second lone pair acceptor orbital, 18, for C5 is 49.5 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C4 with
the antibonding acceptor orbital, 116, for C1-C3 is 28.1 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C4 with
the antibonding acceptor orbital, 118, for C3-C4 is 28.1 kJ/mol.
The interaction of bonding donor orbital, 5, for C3-C4 with
the second lone pair acceptor orbital, 18, for C5 is 51.8 kJ/mol.
The interaction of bonding donor orbital, 5, for C3-C4 with
the antibonding acceptor orbital, 114, for C1-C2 is 97.4 kJ/mol.
The interaction of bonding donor orbital, 5, for C3-C4 with
the antibonding acceptor orbital, 117, for C1-C4 is 26.1 kJ/mol.
The interaction of bonding donor orbital, 6, for C4-C5 with
the antibonding acceptor orbital, 117, for C1-C4 is 22.6 kJ/mol.
The interaction of bonding donor orbital, 6, for C4-C5 with
the antibonding acceptor orbital, 118, for C3-C4 is 20.0 kJ/mol.
The interaction of the second bonding donor orbital, 7, for C4-C5 with
the second lone pair acceptor orbital, 16, for C3 is 186. kJ/mol.
The interaction of the second bonding donor orbital, 7, for C4-C5 with
the second antibonding acceptor orbital, 115, for C1-C2 is 60.7 kJ/mol.
The interaction of lone pair donor orbital, 13, for C2 with
the antibonding acceptor orbital, 116, for C1-C3 is 34.7 kJ/mol.
The interaction of lone pair donor orbital, 13, for C2 with
the antibonding acceptor orbital, 117, for C1-C4 is 37.6 kJ/mol.
The interaction of the second lone pair donor orbital, 14, for C2 with
the antibonding acceptor orbital, 117, for C1-C4 is 23.1 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for C3 with
the second antibonding acceptor orbital, 115, for C1-C2 is 73.7 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for C3 with
the second antibonding acceptor orbital, 120, for C4-C5 is 73.6 kJ/mol.
The interaction of lone pair donor orbital, 17, for C5 with
the antibonding acceptor orbital, 117, for C1-C4 is 37.6 kJ/mol.
The interaction of lone pair donor orbital, 17, for C5 with
the antibonding acceptor orbital, 118, for C3-C4 is 34.7 kJ/mol.
The interaction of the second lone pair donor orbital, 18, for C5 with
the antibonding acceptor orbital, 117, for C1-C4 is 23.1 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.
19 ----- -1.689
18 ----- -4.243
17 ----- -5.968
16 ----- -6.237
15 -^-v- -7.985
14 -^-v- -8.168
13 -^-v- -8.245
12 -^-v- -8.410
11 -^-v- -11.62
10 -^-v- -11.88
9 -^-v- -13.11
8 -^-v- -19.12
7 -^-v- -19.85
6 -^-v- -24.63
5 -^-v- -269.3 4 -^-v- -269.3
3 -^-v- -269.8 2 -^-v- -269.8
1 -^-v- -270.4
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 = -190.1480554297 Hartrees
Top of page.
-> Return to Molecular Structure Page.
-> Return to Chemistry Home Page