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 0.9967 electrons
__has 51.31% C 1 character in a sp1.87 hybrid
__has 48.69% C 2 character in a sp2.42 hybrid
2. A bonding orbital for C1-H6 with 0.9916 electrons
__has 60.96% C 1 character in a sp2.44 hybrid
__has 39.04% H 6 character in a s orbital
3. A bonding orbital for C1-C7 with 0.9971 electrons
__has 50.27% C 1 character in a sp1.85 hybrid
__has 49.73% C 7 character in a sp1.93 hybrid
4. A bonding orbital for C2-H3 with 0.9962 electrons
__has 59.19% C 2 character in a s0.94 p3 hybrid
__has 40.81% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9974 electrons
__has 58.21% C 2 character in a s0.88 p3 hybrid
__has 41.79% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 0.9962 electrons
__has 59.11% C 2 character in a s0.95 p3 hybrid
__has 40.89% H 5 character in a s orbital
7. A bonding orbital for C7-H8 with 0.9937 electrons
__has 59.80% C 7 character in a sp2.74 hybrid
__has 40.20% H 8 character in a s orbital
8. A bonding orbital for C7-H9 with 0.9936 electrons
__has 60.06% C 7 character in a sp2.72 hybrid
__has 39.94% H 9 character in a s orbital
9. A bonding orbital for C7-Cl10 with 0.9966 electrons
__has 28.69% C 7 character in a s0.44 p3 hybrid
__has 71.31% Cl10 character in a s0.53 p3 hybrid
18. A lone pair orbital for C1 with 0.8881 electrons
__made from a p3 hybrid
19. A lone pair orbital for Cl10 with 0.9993 electrons
__made from a sp0.19 hybrid
20. A lone pair orbital for Cl10 with 0.9960 electrons
__made from a p3 hybrid
21. A lone pair orbital for Cl10 with 0.9959 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 7 Cl10 Cl10 Cl10 Cl10 Cl10 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9968 electrons
__has 46.76% C 1 character in a sp1.85 hybrid
__has 53.24% C 2 character in a sp2.31 hybrid
2. A bonding orbital for C1-H6 with 0.9924 electrons
__has 55.93% C 1 character in a sp2.37 hybrid
__has 44.07% H 6 character in a s orbital
3. A bonding orbital for C1-C7 with 0.9974 electrons
__has 45.98% C 1 character in a sp1.83 hybrid
__has 54.02% C 7 character in a sp1.91 hybrid
4. A bonding orbital for C2-H3 with 0.9919 electrons
__has 60.67% C 2 character in a s0.92 p3 hybrid
__has 39.33% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9814 electrons
__has 62.49% C 2 character in a s0.89 p3 hybrid
__has 37.51% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 0.9942 electrons
__has 60.12% C 2 character in a s0.93 p3 hybrid
__has 39.88% H 5 character in a s orbital
7. A bonding orbital for C7-H8 with 0.9940 electrons
__has 61.06% C 7 character in a sp2.89 hybrid
__has 38.94% H 8 character in a s orbital
8. A bonding orbital for C7-H9 with 0.9936 electrons
__has 61.24% C 7 character in a sp2.87 hybrid
__has 38.76% H 9 character in a s orbital
9. A bonding orbital for C7-Cl10 with 0.9795 electrons
__has 47.19% C 7 character in a s0.50 p3 hybrid
__has 52.81% Cl10 character in a s0.29 p3 hybrid
19. A lone pair orbital for Cl10 with 0.9994 electrons
__made from a sp0.17 hybrid
20. A lone pair orbital for Cl10 with 0.9960 electrons
__made from a p-pi orbital ( 99.99% p)
21. A lone pair orbital for Cl10 with 0.9912 electrons
__made from a s0.20 p3 hybrid
-With core pairs on: C 1 C 2 C 7 Cl10 Cl10 Cl10 Cl10 Cl10 -
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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, 5, for C2-H4 with
the lone pair acceptor orbital, 18, for C1 is 32.5 kJ/mol.
The interaction of bonding donor orbital, 9, for C7-Cl10 with
the lone pair acceptor orbital, 18, for C1 is 35.1 kJ/mol.
The interaction of lone pair donor orbital, 18, for C1 with
the antibonding acceptor orbital, 139, for C7-Cl10 is 75.5 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.
25 ----- 1.883
24 ----- 1.586
23 ----- 1.561
22 ----- -0.951
21 -^--- -5.129
20 -^-v- -6.841
19 -^-v- -6.993
18 -^-v- -9.178
17 -^-v- -9.561
16 -^-v- -9.661
15 -^-v- -10.70
14 -^-v- -11.05
13 -^-v- -12.09
12 -^-v- -14.34
11 -^-v- -17.11
10 -^-v- -19.15
9 -^-v- -20.71
8 -^-v- -189.3
7 -^-v- -189.4
6 -^-v- -189.7
5 -^-v- -247.8
4 -^-v- -266.6
3 -^-v- -267.5
2 -^-v- -267.9
1 -^-v- -2729.
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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 = -578.1572806860 Hartrees
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