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 0.9952 electrons
__has 50.86% C 1 character in a sp2.68 hybrid
__has 49.14% C 2 character in a sp2.47 hybrid
2. A bonding orbital for C1-C6 with 0.9952 electrons
__has 50.76% C 1 character in a sp2.69 hybrid
__has 49.24% C 6 character in a sp2.48 hybrid
3. A bonding orbital for C1-C10 with 0.9959 electrons
__has 50.91% C 1 character in a sp2.71 hybrid
__has 49.09% C10 character in a sp1.75 hybrid
4. A bonding orbital for C1-H13 with 0.9904 electrons
__has 56.44% C 1 character in a s0.71 p3 hybrid
__has 43.56% H13 character in a s orbital
5. A bonding orbital for C2-H3 with 0.9962 electrons
__has 59.16% C 2 character in a s0.94 p3 hybrid
__has 40.84% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9963 electrons
__has 59.10% C 2 character in a s0.93 p3 hybrid
__has 40.90% H 4 character in a s orbital
7. A bonding orbital for C2-H5 with 0.9962 electrons
__has 59.18% C 2 character in a s0.94 p3 hybrid
__has 40.82% H 5 character in a s orbital
8. A bonding orbital for C6-H7 with 0.9963 electrons
__has 59.13% C 6 character in a s0.94 p3 hybrid
__has 40.87% H 7 character in a s orbital
9. A bonding orbital for C6-H8 with 0.9962 electrons
__has 59.18% C 6 character in a s0.94 p3 hybrid
__has 40.82% H 8 character in a s orbital
10. A bonding orbital for C6-H9 with 0.9963 electrons
__has 59.11% C 6 character in a s0.93 p3 hybrid
__has 40.89% H 9 character in a s orbital
11. A bonding orbital for C10-H11 with 0.9960 electrons
__has 60.25% C10 character in a sp2.16 hybrid
__has 39.75% H11 character in a s orbital
12. A bonding orbital for C10-H12 with 0.9959 electrons
__has 60.21% C10 character in a sp2.17 hybrid
__has 39.79% H12 character in a s orbital
17. A lone pair orbital for C10 with 0.9755 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 6 C10 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9937 electrons
__has 51.85% C 1 character in a sp2.77 hybrid
__has 48.15% C 2 character in a sp2.51 hybrid
2. A bonding orbital for C1-C6 with 0.9931 electrons
__has 51.96% C 1 character in a sp2.78 hybrid
__has 48.04% C 6 character in a sp2.53 hybrid
3. A bonding orbital for C1-C10 with 0.9952 electrons
__has 56.00% C 1 character in a sp2.56 hybrid
__has 44.00% C10 character in a sp1.78 hybrid
4. A bonding orbital for C1-H13 with 0.9754 electrons
__has 60.85% C 1 character in a s0.71 p3 hybrid
__has 39.15% H13 character in a s orbital
5. A bonding orbital for C2-H3 with 0.9965 electrons
__has 59.06% C 2 character in a s0.94 p3 hybrid
__has 40.94% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9965 electrons
__has 58.98% C 2 character in a s0.93 p3 hybrid
__has 41.02% H 4 character in a s orbital
7. A bonding orbital for C2-H5 with 0.9963 electrons
__has 59.03% C 2 character in a s0.94 p3 hybrid
__has 40.97% H 5 character in a s orbital
8. A bonding orbital for C6-H7 with 0.9965 electrons
__has 59.07% C 6 character in a s0.95 p3 hybrid
__has 40.93% H 7 character in a s orbital
9. A bonding orbital for C6-H8 with 0.9963 electrons
__has 59.01% C 6 character in a s0.94 p3 hybrid
__has 40.99% H 8 character in a s orbital
10. A bonding orbital for C6-H9 with 0.9965 electrons
__has 58.98% C 6 character in a s0.93 p3 hybrid
__has 41.02% H 9 character in a s orbital
11. A bonding orbital for C10-H11 with 0.9969 electrons
__has 54.77% C10 character in a sp2.12 hybrid
__has 45.23% H11 character in a s orbital
12. A bonding orbital for C10-H12 with 0.9969 electrons
__has 54.74% C10 character in a sp2.13 hybrid
__has 45.26% H12 character in a s orbital
-With core pairs on: C 1 C 2 C 6 C10 -
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, 4, for C1-H13 with
the lone pair acceptor orbital, 17, for C10 is 32.4 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.
Only the spin up electron orbital energies are given.
21 ----- 2.134
20 ----- 2.067
19 ----- 1.904
18 ----- 1.591
17 -^--- -4.508
16 -^-v- -8.094
15 -^-v- -8.128
14 -^-v- -8.472
13 -^-v- -8.859
12 -^-v- -9.277
11 -^-v- -10.60
10 -^-v- -10.83
9 -^-v- -11.24
8 -^-v- -13.55
7 -^-v- -16.37
6 -^-v- -16.66
5 -^-v- -19.79
4 -^-v- -265.9
3 -^-v- -265.9
2 -^-v- -266.5
1 -^-v- -266.6
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 = -157.8267739477 Hartrees
Top of page.
-> Return to Molecular Structure Page.
-> Return to Chemistry Home Page