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 O1-C2 with 0.9985 electrons
__has 71.98% O 1 character in a sp1.78 hybrid
__has 28.02% C 2 character in a s0.79 p3 hybrid
2. A bonding orbital for O1-H12 with 0.9952 electrons
__has 78.75% O 1 character in a s0.79 p3 hybrid
__has 21.25% H12 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9950 electrons
__has 53.99% C 2 character in a sp2.51 hybrid
__has 46.01% C 3 character in a s0.97 p3 hybrid
4. A bonding orbital for C2-C7 with 0.9971 electrons
__has 53.77% C 2 character in a sp1.92 hybrid
__has 46.23% C 7 character in a sp2.71 hybrid
5. A bonding orbital for C2-H11 with 0.9899 electrons
__has 57.75% C 2 character in a s0.60 p3 hybrid
__has 42.25% H11 character in a s orbital
6. A bonding orbital for C3-H4 with 0.9933 electrons
__has 61.96% C 3 character in a sp2.80 hybrid
__has 38.04% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9956 electrons
__has 62.02% C 3 character in a sp2.77 hybrid
__has 37.98% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 0.9963 electrons
__has 60.66% C 3 character in a s0.88 p3 hybrid
__has 39.34% H 6 character in a s orbital
9. A bonding orbital for C7-H8 with 0.9937 electrons
__has 60.92% C 7 character in a s0.91 p3 hybrid
__has 39.08% H 8 character in a s orbital
10. A bonding orbital for C7-H9 with 0.9937 electrons
__has 61.10% C 7 character in a s0.97 p3 hybrid
__has 38.90% H 9 character in a s orbital
11. A bonding orbital for C7-H10 with 0.9907 electrons
__has 62.64% C 7 character in a sp2.91 hybrid
__has 37.36% H10 character in a s orbital
16. A lone pair orbital for O1 with 0.9939 electrons
__made from a sp1.32 hybrid
17. A lone pair orbital for O1 with 0.9893 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 7 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9983 electrons
__has 68.01% O 1 character in a sp1.71 hybrid
__has 31.99% C 2 character in a s0.80 p3 hybrid
2. A bonding orbital for O1-H12 with 0.9954 electrons
__has 75.20% O 1 character in a s0.84 p3 hybrid
__has 24.80% H12 character in a s orbital
3. A bonding orbital for C2-C3 with 0.9291 electrons
__has 58.62% C 2 character in a sp2.52 hybrid
__has 41.38% C 3 character in a s0.95 p3 hybrid
4. A bonding orbital for C2-C7 with 0.9945 electrons
__has 53.96% C 2 character in a sp1.90 hybrid
__has 46.04% C 7 character in a sp2.72 hybrid
5. A bonding orbital for C2-H11 with 0.8315 electrons
__has 70.29% C 2 character in a s0.58 p3 hybrid
__has 29.71% H11 character in a s orbital
6. A bonding orbital for C3-H4 with 0.9924 electrons
__has 61.51% C 3 character in a sp2.84 hybrid
__has 38.49% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9958 electrons
__has 61.48% C 3 character in a sp2.85 hybrid
__has 38.52% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 0.9857 electrons
__has 61.33% C 3 character in a s0.94 p3 hybrid
__has 38.67% H 6 character in a s orbital
9. A bonding orbital for C7-H8 with 0.9911 electrons
__has 61.43% C 7 character in a s0.93 p3 hybrid
__has 38.57% H 8 character in a s orbital
10. A bonding orbital for C7-H9 with 0.9933 electrons
__has 61.20% C 7 character in a s0.95 p3 hybrid
__has 38.80% H 9 character in a s orbital
11. A bonding orbital for C7-H10 with 0.9915 electrons
__has 62.49% C 7 character in a sp2.92 hybrid
__has 37.51% H10 character in a s orbital
16. A lone pair orbital for O1 with 0.9929 electrons
__made from a sp1.42 hybrid
17. A lone pair orbital for O1 with 0.2451 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 7 -
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, 3, for C2-C3 with
the second lone pair acceptor orbital, 17, for O1 is 40.4 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H11 with
the second lone pair acceptor orbital, 17, for O1 is 206. 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 ----- -3.102
20 ----- -3.266
19 ----- -4.381
18 ----- -5.245
17 -^--- -13.45
16 -^-v- -14.85
15 -^-v- -14.99
14 -^-v- -15.38
13 -^-v- -15.54
12 -^-v- -15.82
11 -^-v- -17.49
10 -^-v- -18.22
9 -^-v- -19.50
8 -^-v- -21.73
7 -^-v- -23.37
6 -^-v- -25.84
5 -^-v- -33.58
4 -^-v- -272.1
3 -^-v- -272.5
2 -^-v- -275.4
1 -^-v- -514.9
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 = -194.0695521262 Hartrees
Top of page.
-> Return to Molecular Structure Page.
-> Return to Chemistry Home Page