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.
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 0.9943 electrons
__has 51.69% C 1 character in a sp1.90 hybrid
__has 48.31% C 2 character in a sp2.40 hybrid
2. A bonding orbital for C1-C6 with 0.9941 electrons
__has 51.64% C 1 character in a sp1.94 hybrid
__has 48.36% C 6 character in a sp2.41 hybrid
3. A bonding orbital for C1-C10 with 0.9953 electrons
__has 50.33% C 1 character in a sp2.15 hybrid
__has 49.67% C10 character in a sp1.69 hybrid
4. A bonding orbital for C1-C10 with 0.9912 electrons
__has 33.24% C 1 character in a p-pi orbital ( 99.68% p 0.32% d)
__has 66.76% C10 character in a p-pi orbital ( 99.83% p 0.17% d)
5. A bonding orbital for C2-H3 with 0.9817 electrons
__has 62.32% C 2 character in a s0.87 p3 hybrid
__has 37.68% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9951 electrons
__has 62.00% C 2 character in a sp2.85 hybrid
__has 38.00% H 4 character in a s orbital
7. A bonding orbital for C2-H5 with 0.9817 electrons
__has 62.32% C 2 character in a s0.86 p3 hybrid
__has 37.68% H 5 character in a s orbital
8. A bonding orbital for C6-H7 with 0.9845 electrons
__has 62.30% C 6 character in a s0.86 p3 hybrid
__has 37.70% H 7 character in a s orbital
9. A bonding orbital for C6-H8 with 0.9949 electrons
__has 62.38% C 6 character in a sp2.84 hybrid
__has 37.62% H 8 character in a s orbital
10. A bonding orbital for C6-H9 with 0.9846 electrons
__has 62.30% C 6 character in a s0.87 p3 hybrid
__has 37.70% H 9 character in a s orbital
11. A bonding orbital for C10-H11 with 0.9947 electrons
__has 62.44% C10 character in a sp2.15 hybrid
__has 37.56% H11 character in a s orbital
12. A bonding orbital for C10-H12 with 0.9946 electrons
__has 62.26% C10 character in a sp2.18 hybrid
__has 37.74% H12 character in a s orbital
-With core pairs on: C 1 C 2 C 6 C10 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9945 electrons
__has 50.72% C 1 character in a sp1.93 hybrid
__has 49.28% C 2 character in a sp2.36 hybrid
2. A bonding orbital for C1-C6 with 0.9943 electrons
__has 50.73% C 1 character in a sp1.97 hybrid
__has 49.27% C 6 character in a sp2.38 hybrid
3. A bonding orbital for C1-C10 with 0.9950 electrons
__has 52.32% C 1 character in a sp2.08 hybrid
__has 47.68% C10 character in a sp1.72 hybrid
4. A bonding orbital for C2-H3 with 0.9686 electrons
__has 63.82% C 2 character in a s0.86 p3 hybrid
__has 36.18% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9951 electrons
__has 62.07% C 2 character in a sp2.86 hybrid
__has 37.93% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 0.9685 electrons
__has 63.83% C 2 character in a s0.86 p3 hybrid
__has 36.17% H 5 character in a s orbital
7. A bonding orbital for C6-H7 with 0.9684 electrons
__has 63.35% C 6 character in a s0.86 p3 hybrid
__has 36.65% H 7 character in a s orbital
8. A bonding orbital for C6-H8 with 0.9952 electrons
__has 62.30% C 6 character in a sp2.85 hybrid
__has 37.70% H 8 character in a s orbital
9. A bonding orbital for C6-H9 with 0.9685 electrons
__has 63.35% C 6 character in a s0.86 p3 hybrid
__has 36.65% H 9 character in a s orbital
10. A bonding orbital for C10-H11 with 0.9953 electrons
__has 58.84% C10 character in a sp2.14 hybrid
__has 41.16% H11 character in a s orbital
11. A bonding orbital for C10-H12 with 0.9952 electrons
__has 58.68% C10 character in a sp2.17 hybrid
__has 41.32% H12 character in a s orbital
16. A lone pair orbital for C1 with 0.1088 electrons
__made from a p-pi orbital ( 99.96% p)
-With core pairs on: C 1 C 2 C 6 C10 -
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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, 4, for C2-H3 with
the lone pair acceptor orbital, 16, for C1 is 37.2 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H5 with
the lone pair acceptor orbital, 16, for C1 is 37.3 kJ/mol.
The interaction of bonding donor orbital, 7, for C6-H7 with
the lone pair acceptor orbital, 16, for C1 is 36.3 kJ/mol.
The interaction of bonding donor orbital, 9, for C6-H9 with
the lone pair acceptor orbital, 16, for C1 is 36.1 kJ/mol.
The interaction of lone pair donor orbital, 16, for C1 with
the lone pair acceptor orbital, 17, for C10 is 59.9 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.
Only the spin up electron orbital energies are given.
20 ----- -2.712
19 ----- -2.868
18 ----- -3.618
17 ----- -8.325
16 -^--- -12.99
15 -^-v- -14.75
14 -^-v- -15.02
13 -^-v- -15.14
12 -^-v- -15.26
11 -^-v- -16.76
10 -^-v- -17.34
9 -^-v- -17.58
8 -^-v- -19.30
7 -^-v- -23.17
6 -^-v- -23.30
5 -^-v- -26.82
4 -^-v- -272.0
3 -^-v- -272.1
2 -^-v- -273.9
1 -^-v- -274.5
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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 = -156.9394476178 Hartrees
Note: The results for a higher energy conformer are also available.
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