
Tell me about the atomic charges, dipole moment,
bond lengths,
angles,
bond orders,
molecular orbital energies,
or total energy.
Tell me about the best Lewis structure.
The Lewis structure is built for the up and down electrons,
separately. Note that the up and down structures can be very
different.
1. A bonding orbital for H1O2 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 O2C3 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 O2C3 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 C3C4 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 C3C13 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 C4H5 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 C4H6 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 C4C7 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 C7H8 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 C7H9 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 C7C10 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 C10H11 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 C10H12 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 C13H14 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 C13H15 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 C13H16 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 
1. A bonding orbital for H1O2 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 O2C3 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 O2C3 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 C3C4 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 C3C13 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 C4H5 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 C4H6 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 C4C7 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 C7H8 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 C7H9 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 C7C10 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 C10H11 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 C10H12 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 C13H14 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 C13H15 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 C13H16 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 
The interaction of bonding donor orbital, 1, for H1O2 with the lone pair acceptor orbital, 24, for C10 is 28.2 kJ/mol.
The interaction of bonding donor orbital, 6, for C4H5 with the second antibonding acceptor orbital, 167, for O2C3 is 33.5 kJ/mol.
The interaction of bonding donor orbital, 10, for C7H9 with the lone pair acceptor orbital, 24, for C10 is 41.6 kJ/mol.
The interaction of bonding donor orbital, 16, for C13H16 with the second antibonding acceptor orbital, 167, for O2C3 is 36.3 kJ/mol.
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
Total electronic energy = 271.5387582757 Hartrees
Note: This ion results from the McLafferty rearrangemnt of
2pentanone radical cation, CH_{3}CH_{2}CH_{2}COCH_{3}^{+}•.
Other similar conformations of this ion dissociate in
calculations to ethylene and
propenol radical cation, H_{2}C=COHCH_{3}^{+}•.
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.