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-N2 with 0.9971 electrons
__has 39.33% C 1 character in a s0.88 p3 hybrid
__has 60.67% N 2 character in a sp2.17 hybrid
2. A bonding orbital for C1-C5 with 0.9970 electrons
__has 50.31% C 1 character in a sp2.60 hybrid
__has 49.69% C 5 character in a sp1.80 hybrid
3. A bonding orbital for C1-C8 with 0.9955 electrons
__has 51.10% C 1 character in a sp2.53 hybrid
__has 48.90% C 8 character in a sp2.56 hybrid
4. A bonding orbital for C1-H12 with 0.9893 electrons
__has 58.10% C 1 character in a s0.82 p3 hybrid
__has 41.90% H12 character in a s orbital
5. A bonding orbital for N2-H3 with 0.9961 electrons
__has 67.39% N 2 character in a s0.97 p3 hybrid
__has 32.61% H 3 character in a s orbital
6. A bonding orbital for N2-H4 with 0.9961 electrons
__has 67.61% N 2 character in a s0.97 p3 hybrid
__has 32.39% H 4 character in a s orbital
7. A bonding orbital for C5-H6 with 0.9956 electrons
__has 60.02% C 5 character in a sp2.18 hybrid
__has 39.98% H 6 character in a s orbital
8. A bonding orbital for C5-H7 with 0.9957 electrons
__has 60.26% C 5 character in a sp2.15 hybrid
__has 39.74% H 7 character in a s orbital
9. A bonding orbital for C8-H9 with 0.9960 electrons
__has 58.82% C 8 character in a s0.93 p3 hybrid
__has 41.18% H 9 character in a s orbital
10. A bonding orbital for C8-H10 with 0.9956 electrons
__has 59.30% C 8 character in a s0.94 p3 hybrid
__has 40.70% H10 character in a s orbital
11. A bonding orbital for C8-H11 with 0.9960 electrons
__has 59.92% C 8 character in a s0.96 p3 hybrid
__has 40.08% H11 character in a s orbital
16. A lone pair orbital for N2 with 0.9901 electrons
__made from a s0.72 p3 hybrid
17. A lone pair orbital for C5 with 0.9738 electrons
__made from a p3 hybrid
-With core pairs on: C 1 N 2 C 5 C 8 -
Up Electrons
1. A bonding orbital for C1-N2 with 0.9890 electrons
__has 43.66% C 1 character in a s0.90 p3 hybrid
__has 56.34% N 2 character in a sp2.67 hybrid
2. A bonding orbital for C1-C5 with 0.9965 electrons
__has 55.34% C 1 character in a sp2.49 hybrid
__has 44.66% C 5 character in a sp1.80 hybrid
3. A bonding orbital for C1-C8 with 0.9946 electrons
__has 51.95% C 1 character in a sp2.62 hybrid
__has 48.05% C 8 character in a sp2.58 hybrid
4. A bonding orbital for C1-H12 with 0.9884 electrons
__has 59.02% C 1 character in a s0.79 p3 hybrid
__has 40.98% H12 character in a s orbital
5. A bonding orbital for N2-H3 with 0.9958 electrons
__has 66.78% N 2 character in a s0.93 p3 hybrid
__has 33.22% H 3 character in a s orbital
6. A bonding orbital for N2-H4 with 0.9957 electrons
__has 67.01% N 2 character in a s0.94 p3 hybrid
__has 32.99% H 4 character in a s orbital
7. A bonding orbital for C5-H6 with 0.9967 electrons
__has 54.61% C 5 character in a sp2.13 hybrid
__has 45.39% H 6 character in a s orbital
8. A bonding orbital for C5-H7 with 0.9967 electrons
__has 54.85% C 5 character in a sp2.10 hybrid
__has 45.15% H 7 character in a s orbital
9. A bonding orbital for C8-H9 with 0.9962 electrons
__has 58.69% C 8 character in a s0.93 p3 hybrid
__has 41.31% H 9 character in a s orbital
10. A bonding orbital for C8-H10 with 0.9954 electrons
__has 59.17% C 8 character in a s0.94 p3 hybrid
__has 40.83% H10 character in a s orbital
11. A bonding orbital for C8-H11 with 0.9961 electrons
__has 59.92% C 8 character in a s0.97 p3 hybrid
__has 40.08% H11 character in a s orbital
16. A lone pair orbital for N2 with 0.9775 electrons
__made from a sp2.97 hybrid
-With core pairs on: C 1 N 2 C 5 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.
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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.
21 ----- 2.264
20 ----- 2.112
19 ----- 1.935
18 ----- 1.188
17 -^--- -4.430
16 -^-v- -6.317
15 -^-v- -8.182
14 -^-v- -8.793
13 -^-v- -8.952
12 -^-v- -10.09
11 -^-v- -10.68
10 -^-v- -11.07
9 -^-v- -12.31
8 -^-v- -14.10
7 -^-v- -16.50
6 -^-v- -18.38
5 -^-v- -22.02
4 -^-v- -265.9
3 -^-v- -266.4
2 -^-v- -267.2
1 -^-v- -377.1
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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 = -173.8768236550 Hartrees
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