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.
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 0.9961 electrons
__has 49.97% C 1 character in a sp1.65 hybrid
__has 50.03% C 2 character in a sp1.58 hybrid
2. A bonding orbital for C1-C5 with 0.9963 electrons
__has 47.98% C 1 character in a sp1.85 hybrid
__has 52.02% C 5 character in a sp1.37 hybrid
3. A bonding orbital for C1-H8 with 0.9857 electrons
__has 58.39% C 1 character in a sp2.63 hybrid
__has 41.61% H 8 character in a s orbital
4. A bonding orbital for C2-H3 with 0.9943 electrons
__has 60.91% C 2 character in a sp2.25 hybrid
__has 39.09% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9942 electrons
__has 61.25% C 2 character in a sp2.23 hybrid
__has 38.75% H 4 character in a s orbital
6. A bonding orbital for C5-Cl6 with 0.9955 electrons
__has 45.93% C 5 character in a sp2.97 hybrid
__has 54.07% Cl 6 character in a s0.59 p3 hybrid
7. A bonding orbital for C5-H7 with 0.9933 electrons
__has 62.49% C 5 character in a sp2.04 hybrid
__has 37.51% H 7 character in a s orbital
16. A lone pair orbital for C1 with 0.2887 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)
17. A lone pair orbital for C2 with 0.8432 electrons
__made from a p-pi orbital ( 99.97% p)
18. A lone pair orbital for C5 with 0.8674 electrons
__made from a p-pi orbital ( 99.99% p)
19. A lone pair orbital for Cl6 with 0.9974 electrons
__made from a sp0.20 hybrid
20. A lone pair orbital for Cl6 with 0.9932 electrons
__made from a p-pi orbital (100.00% p)
21. A lone pair orbital for Cl6 with 0.9880 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 5 Cl 6 Cl 6 Cl 6 Cl 6 Cl 6 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9957 electrons
__has 54.79% C 1 character in a sp1.63 hybrid
__has 45.21% C 2 character in a sp1.64 hybrid
2. A bonding orbital for C1-C2 with 0.8677 electrons
__has 84.85% C 1 character in a p-pi orbital ( 99.98% p)
__has 15.15% C 2 character in a p-pi orbital ( 99.78% p 0.22% d)
3. A bonding orbital for C1-C5 with 0.9961 electrons
__has 53.23% C 1 character in a sp1.80 hybrid
__has 46.77% C 5 character in a sp1.44 hybrid
4. A bonding orbital for C1-H8 with 0.9854 electrons
__has 61.40% C 1 character in a sp2.76 hybrid
__has 38.60% H 8 character in a s orbital
5. A bonding orbital for C2-H3 with 0.9951 electrons
__has 56.64% C 2 character in a sp2.22 hybrid
__has 43.36% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9947 electrons
__has 57.12% C 2 character in a sp2.19 hybrid
__has 42.88% H 4 character in a s orbital
7. A bonding orbital for C5-Cl6 with 0.9964 electrons
__has 41.17% C 5 character in a sp2.84 hybrid
__has 58.83% Cl 6 character in a s0.69 p3 hybrid
8. A bonding orbital for C5-H7 with 0.9943 electrons
__has 57.82% C 5 character in a sp2.02 hybrid
__has 42.18% H 7 character in a s orbital
17. A lone pair orbital for C5 with 0.1789 electrons
__made from a p-pi orbital ( 99.87% p 0.13% d)
18. A lone pair orbital for Cl6 with 0.9976 electrons
__made from a sp0.23 hybrid
19. A lone pair orbital for Cl6 with 0.9870 electrons
__made from a p3 hybrid
20. A lone pair orbital for Cl6 with 0.9518 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
-With core pairs on: C 1 C 2 C 5 Cl 6 Cl 6 Cl 6 Cl 6 Cl 6 -
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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 bonding donor orbital, 2, for C1-C2 with
the lone pair acceptor orbital, 17, for C5 is 263. kJ/mol.
The interaction of the third lone pair donor orbital, 20, for Cl6 with
the lone pair acceptor orbital, 17, for C5 is 88.6 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.
24 ----- 2.123
23 ----- 1.742
22 ----- -0.330
21 ----- -0.544
20 -^--- -4.802
19 -^-v- -7.528
18 -^-v- -7.749
17 -^-v- -9.127
16 -^-v- -9.444
15 -^-v- -10.15
14 -^-v- -11.34
13 -^-v- -12.47
12 -^-v- -13.68
11 -^-v- -16.71
10 -^-v- -19.41
9 -^-v- -22.00
8 -^-v- -190.5
7 -^-v- -190.6
6 -^-v- -190.9
5 -^-v- -249.0
4 -^-v- -266.7
3 -^-v- -266.9
2 -^-v- -268.3
1 -^-v- -2730.
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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 = -576.9416853441 Hartrees
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