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 0.9458 electrons
__has 76.84% O 1 character in a s0.87 p3 hybrid
__has 23.16% C 2 character in a s0.88 p3 d0.95 hybrid
2. A bonding orbital for O1-C2 with 0.9321 electrons
__has 85.89% O 1 character in a s0.50 p3 hybrid
__has 14.11% C 2 character in a s0.84 p3 d2.07 hybrid
3. A bonding orbital for C2-N3 with 0.9898 electrons
__has 38.13% C 2 character in a sp2.29 hybrid
__has 61.87% N 3 character in a sp1.82 hybrid
4. A bonding orbital for C2-N3 with 0.9478 electrons
__has 7.52% C 2 character in a s0.13 p3 d1.70 hybrid
__has 92.48% N 3 character in a p3 hybrid
5. A bonding orbital for C2-C8 with 0.9907 electrons
__has 48.77% C 2 character in a sp1.72 hybrid
__has 51.23% C 8 character in a sp2.76 hybrid
6. A bonding orbital for N3-C4 with 0.9946 electrons
__has 61.59% N 3 character in a sp1.87 hybrid
__has 38.41% C 4 character in a sp2.87 hybrid
7. A bonding orbital for C4-H5 with 0.9965 electrons
__has 58.57% C 4 character in a s0.98 p3 hybrid
__has 41.43% H 5 character in a s orbital
8. A bonding orbital for C4-H6 with 0.9977 electrons
__has 57.99% C 4 character in a s0.90 p3 hybrid
__has 42.01% H 6 character in a s orbital
9. A bonding orbital for C4-H7 with 0.9983 electrons
__has 59.17% C 4 character in a sp2.74 hybrid
__has 40.83% H 7 character in a s orbital
10. A bonding orbital for C8-H9 with 0.9871 electrons
__has 61.38% C 8 character in a s0.96 p3 hybrid
__has 38.62% H 9 character in a s orbital
11. A bonding orbital for C8-H10 with 0.9945 electrons
__has 60.43% C 8 character in a s0.98 p3 hybrid
__has 39.57% H10 character in a s orbital
12. A bonding orbital for C8-H11 with 0.9929 electrons
__has 60.81% C 8 character in a s0.97 p3 hybrid
__has 39.19% H11 character in a s orbital
18. A lone pair orbital for O1 with 0.9912 electrons
__made from a sp0.59 hybrid
19. A lone pair orbital for O1 with 0.9653 electrons
__made from a p3 hybrid
20. A lone pair orbital for N3 with 0.9739 electrons
__made from a sp2.41 hybrid
-With core pairs on: O 1 C 2 N 3 C 4 C 8 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9985 electrons
__has 62.42% O 1 character in a sp1.77 hybrid
__has 37.58% C 2 character in a sp2.22 hybrid
2. A bonding orbital for O1-C2 with 0.9482 electrons
__has 44.05% O 1 character in a p3 hybrid
__has 55.95% C 2 character in a p3 hybrid
3. A bonding orbital for C2-N3 with 0.9963 electrons
__has 43.78% C 2 character in a sp2.11 hybrid
__has 56.22% N 3 character in a sp1.94 hybrid
4. A bonding orbital for C2-C8 with 0.9944 electrons
__has 51.03% C 2 character in a sp1.75 hybrid
__has 48.97% C 8 character in a sp2.82 hybrid
5. A bonding orbital for N3-C4 with 0.9941 electrons
__has 56.71% N 3 character in a sp1.96 hybrid
__has 43.29% C 4 character in a sp2.73 hybrid
6. A bonding orbital for C4-H5 with 0.9881 electrons
__has 60.55% C 4 character in a s0.93 p3 hybrid
__has 39.45% H 5 character in a s orbital
7. A bonding orbital for C4-H6 with 0.9795 electrons
__has 62.25% C 4 character in a s0.95 p3 hybrid
__has 37.75% H 6 character in a s orbital
8. A bonding orbital for C4-H7 with 0.9971 electrons
__has 59.68% C 4 character in a sp2.90 hybrid
__has 40.32% H 7 character in a s orbital
9. A bonding orbital for C8-H9 with 0.9917 electrons
__has 60.10% C 8 character in a s0.96 p3 hybrid
__has 39.90% H 9 character in a s orbital
10. A bonding orbital for C8-H10 with 0.9944 electrons
__has 60.03% C 8 character in a s0.99 p3 hybrid
__has 39.97% H10 character in a s orbital
11. A bonding orbital for C8-H11 with 0.9948 electrons
__has 60.33% C 8 character in a s0.98 p3 hybrid
__has 39.67% H11 character in a s orbital
17. A lone pair orbital for O1 with 0.9903 electrons
__made from a sp0.58 hybrid
18. A lone pair orbital for O1 with 0.9576 electrons
__made from a p3 hybrid
19. A lone pair orbital for N3 with 0.9579 electrons
__made from a sp2.07 hybrid
-With core pairs on: O 1 C 2 N 3 C 4 C 8 -
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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 the second bonding donor orbital, 2, for O1-C2 with
the second lone pair acceptor orbital, 20, for N3 is 88.9 kJ/mol.
The interaction of bonding donor orbital, 7, for C4-H6 with
the second lone pair acceptor orbital, 20, for N3 is 34.7 kJ/mol.
The interaction of the second lone pair donor orbital, 18, for O1 with
the antibonding acceptor orbital, 148, for C2-N3 is 53.0 kJ/mol.
The interaction of the second lone pair donor orbital, 18, for O1 with
the antibonding acceptor orbital, 149, for C2-C8 is 44.0 kJ/mol.
The interaction of lone pair donor orbital, 19, for N3 with
the antibonding acceptor orbital, 146, for O1-C2 is 27.8 kJ/mol.
The interaction of the second lone pair donor orbital, 20, for N3 with
the second antibonding acceptor orbital, 147, for O1-C2 is 50.5 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.
24 ----- 2.343
23 ----- 1.712
22 ----- 1.364
21 ----- -1.301
20 -^--- -6.384
19 -^-v- -6.473
18 -^-v- -7.519
17 -^-v- -8.960
16 -^-v- -9.821
15 -^-v- -10.28
14 -^-v- -10.57
13 -^-v- -11.49
12 -^-v- -11.67
11 -^-v- -12.05
10 -^-v- -13.24
9 -^-v- -17.06
8 -^-v- -18.74
7 -^-v- -22.60
6 -^-v- -26.25
5 -^-v- -266.5
4 -^-v- -267.4
3 -^-v- -269.2
2 -^-v- -378.4
1 -^-v- -506.6
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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 = -247.9393086383 Hartrees
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