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 H1-O2 with 0.9915 electrons
__has 16.69% H 1 character in a s orbital
__has 83.31% O 2 character in a sp2.84 hybrid
2. A bonding orbital for O2-C3 with 0.9979 electrons
__has 67.96% O 2 character in a sp1.78 hybrid
__has 32.04% C 3 character in a sp2.52 hybrid
3. A bonding orbital for O2-C3 with 0.9965 electrons
__has 84.26% O 2 character in a p3 hybrid
__has 15.74% C 3 character in a p3 hybrid
4. A bonding orbital for C3-C4 with 0.9947 electrons
__has 50.36% C 3 character in a sp1.80 hybrid
__has 49.64% C 4 character in a sp2.95 hybrid
5. A bonding orbital for C3-C13 with 0.9949 electrons
__has 51.31% C 3 character in a sp1.77 hybrid
__has 48.69% C13 character in a sp2.64 hybrid
6. A bonding orbital for C4-H5 with 0.9738 electrons
__has 62.49% C 4 character in a s0.82 p3 hybrid
__has 37.51% H 5 character in a s orbital
7. A bonding orbital for C4-H6 with 0.9867 electrons
__has 62.57% C 4 character in a s0.95 p3 hybrid
__has 37.43% H 6 character in a s orbital
8. A bonding orbital for C4-C7 with 0.9923 electrons
__has 53.06% C 4 character in a sp2.43 hybrid
__has 46.94% C 7 character in a sp2.77 hybrid
9. A bonding orbital for C7-H8 with 0.9929 electrons
__has 60.66% C 7 character in a s0.92 p3 hybrid
__has 39.34% H 8 character in a s orbital
10. A bonding orbital for C7-H9 with 0.9941 electrons
__has 60.08% C 7 character in a s0.83 p3 hybrid
__has 39.92% H 9 character in a s orbital
11. A bonding orbital for C7-C10 with 0.9977 electrons
__has 50.11% C 7 character in a sp2.51 hybrid
__has 49.89% C10 character in a sp2.19 hybrid
12. A bonding orbital for C10-H11 with 0.9954 electrons
__has 61.64% C10 character in a sp2.57 hybrid
__has 38.36% H11 character in a s orbital
13. A bonding orbital for C10-H12 with 0.9955 electrons
__has 62.73% C10 character in a sp2.26 hybrid
__has 37.27% H12 character in a s orbital
14. A bonding orbital for C13-H14 with 0.9859 electrons
__has 62.24% C13 character in a s0.96 p3 hybrid
__has 37.76% H14 character in a s orbital
15. A bonding orbital for C13-H15 with 0.9930 electrons
__has 62.96% C13 character in a sp2.84 hybrid
__has 37.04% H15 character in a s orbital
16. A bonding orbital for C13-H16 with 0.9746 electrons
__has 62.73% C13 character in a s0.87 p3 hybrid
__has 37.27% H16 character in a s orbital
23. A lone pair orbital for O2 with 0.9867 electrons
__made from a sp1.62 hybrid
24. A lone pair orbital for C10 with 0.8843 electrons
__made from a s0.34 p3 hybrid
-With core pairs on: O 2 C 3 C 4 C 7 C10 C13 -
Up Electrons
1. A bonding orbital for H1-O2 with 0.9775 electrons
__has 23.61% H 1 character in a s orbital
__has 76.39% O 2 character in a s0.73 p3 hybrid
2. A bonding orbital for O2-C3 with 0.9980 electrons
__has 67.32% O 2 character in a sp1.72 hybrid
__has 32.68% C 3 character in a sp2.51 hybrid
3. A bonding orbital for O2-C3 with 0.9962 electrons
__has 82.83% O 2 character in a p3 hybrid
__has 17.17% C 3 character in a p3 hybrid
4. A bonding orbital for C3-C4 with 0.9939 electrons
__has 50.70% C 3 character in a sp1.81 hybrid
__has 49.30% C 4 character in a sp2.92 hybrid
5. A bonding orbital for C3-C13 with 0.9919 electrons
__has 51.76% C 3 character in a sp1.75 hybrid
__has 48.24% C13 character in a sp2.66 hybrid
6. A bonding orbital for C4-H5 with 0.9741 electrons
__has 62.30% C 4 character in a s0.82 p3 hybrid
__has 37.70% H 5 character in a s orbital
7. A bonding orbital for C4-H6 with 0.9871 electrons
__has 62.33% C 4 character in a s0.95 p3 hybrid
__has 37.67% H 6 character in a s orbital
8. A bonding orbital for C4-C7 with 0.9891 electrons
__has 51.71% C 4 character in a sp2.45 hybrid
__has 48.29% C 7 character in a sp2.92 hybrid
9. A bonding orbital for C7-H8 with 0.9917 electrons
__has 61.32% C 7 character in a s0.88 p3 hybrid
__has 38.68% H 8 character in a s orbital
10. A bonding orbital for C7-H9 with 0.9708 electrons
__has 64.43% C 7 character in a s0.89 p3 hybrid
__has 35.57% H 9 character in a s orbital
11. A bonding orbital for C7-C10 with 0.9961 electrons
__has 53.98% C 7 character in a sp2.45 hybrid
__has 46.02% C10 character in a sp1.79 hybrid
12. A bonding orbital for C10-H11 with 0.9950 electrons
__has 57.71% C10 character in a sp2.16 hybrid
__has 42.29% H11 character in a s orbital
13. A bonding orbital for C10-H12 with 0.9959 electrons
__has 58.51% C10 character in a sp2.08 hybrid
__has 41.49% H12 character in a s orbital
14. A bonding orbital for C13-H14 with 0.9861 electrons
__has 62.19% C13 character in a s0.96 p3 hybrid
__has 37.81% H14 character in a s orbital
15. A bonding orbital for C13-H15 with 0.9931 electrons
__has 62.89% C13 character in a sp2.84 hybrid
__has 37.11% H15 character in a s orbital
16. A bonding orbital for C13-H16 with 0.9747 electrons
__has 62.65% C13 character in a s0.87 p3 hybrid
__has 37.35% H16 character in a s orbital
23. A lone pair orbital for O2 with 0.9857 electrons
__made from a sp1.28 hybrid
-With core pairs on: O 2 C 3 C 4 C 7 C10 C13 -
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, 1, for H1-O2 with
the lone pair acceptor orbital, 24, for C10 is 28.2 kJ/mol.
The interaction of bonding donor orbital, 6, for C4-H5 with
the second antibonding acceptor orbital, 167, for O2-C3 is 33.5 kJ/mol.
The interaction of bonding donor orbital, 10, for C7-H9 with
the lone pair acceptor orbital, 24, for C10 is 41.6 kJ/mol.
The interaction of bonding donor orbital, 16, for C13-H16 with
the second antibonding acceptor orbital, 167, for O2-C3 is 36.3 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.
28 ----- -2.712
27 ----- -3.127
26 ----- -3.559
25 ----- -8.533
24 -^--- -10.50
23 -^-v- -13.57
22 -^-v- -14.17
21 -^-v- -14.37
20 -^-v- -14.77
19 -^-v- -14.91
18 -^-v- -15.38
17 -^-v- -15.55
16 -^-v- -16.15
15 -^-v- -17.05
14 -^-v- -17.48
13 -^-v- -18.20
12 -^-v- -20.05
11 -^-v- -20.79
10 -^-v- -22.50
9 -^-v- -24.59
8 -^-v- -25.54
7 -^-v- -33.42
6 -^-v- -271.7
5 -^-v- -271.8
4 -^-v- -271.9
3 -^-v- -272.3
2 -^-v- -275.5
1 -^-v- -514.1
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 = -271.5387582757 Hartrees
Note: This ion results from the McLafferty rearrangemnt of
2-pentanone radical cation, CH3CH2CH2COCH3+•.
Other similar conformations of this ion dissociate in
calculations to ethylene and
propenol radical cation, H2C=COHCH3+•.
So this calculation should be considered a transient intermediate, at best.
Other lower energy metastable conformers may also exist. The 'all trans'
pentenol radical
cation trans conformer is higher in energy.
* The Lewis Structure calculation (NBO analysis) was run without
diffuse functions to decrease the size of the calculation.
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