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.
Hybridization in the Best Lewis Structure
1. A bonding orbital for C1-N2 with 1.9979 electrons
__has 36.58% C 1 character in a sp2.08 hybrid
__has 63.42% N 2 character in a sp1.42 hybrid
2. A bonding orbital for C1-N2 with 1.9947 electrons
__has 42.37% C 1 character in a p-pi orbital ( 99.79% p 0.21% d)
__has 57.63% N 2 character in a p-pi orbital ( 99.88% p 0.12% d)
3. A bonding orbital for C1-H3 with 1.9902 electrons
__has 60.39% C 1 character in a sp1.90 hybrid
__has 39.61% H 3 character in a s orbital
4. A bonding orbital for C1-H4 with 1.9876 electrons
__has 59.21% C 1 character in a sp1.99 hybrid
__has 40.79% H 4 character in a s orbital
5. A bonding orbital for N2-H5 with 1.9869 electrons
__has 70.00% N 2 character in a sp2.87 hybrid
__has 30.00% H 5 character in a s orbital
6. A bonding orbital for N2-O6 with 1.9966 electrons
__has 53.32% N 2 character in a sp2.00 hybrid
__has 46.68% O 6 character in a s0.76 p3 hybrid
10. A lone pair orbital for O6 with 1.9883 electrons
__made from a sp0.25 hybrid
11. A lone pair orbital for O6 with 1.9375 electrons
__made from a p3 hybrid
12. A lone pair orbital for O6 with 1.7300 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
86. A antibonding orbital for C1-N2 with 0.2627 electrons
__has 57.63% C 1 character in a p-pi orbital ( 99.79% p 0.21% d)
__has 42.37% N 2 character in a p-pi orbital ( 99.88% p 0.12% d)
-With core pairs on: C 1 N 2 O 6 -
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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 bonding donor orbital, 4, for C1-H4 with
the antibonding acceptor orbital, 90, for N2-O6 is 32.9 kJ/mol.
The interaction of lone pair donor orbital, 10, for O6 with
the antibonding acceptor orbital, 85, for C1-N2 is 22.8 kJ/mol.
The interaction of the second lone pair donor orbital, 11, for O6 with
the antibonding acceptor orbital, 85, for C1-N2 is 51.6 kJ/mol.
The interaction of the second lone pair donor orbital, 11, for O6 with
the antibonding acceptor orbital, 89, for N2-H5 is 80.5 kJ/mol.
The interaction of the third lone pair donor orbital, 12, for O6 with
the second antibonding acceptor orbital, 86, for C1-N2 is 444. 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.
16 ----- 2.598
15 ----- 2.070
14 ----- 0.360
13 ----- -2.296
12 -^-v- -5.922
11 -^-v- -6.036
10 -^-v- -10.38
9 -^-v- -11.26
8 -^-v- -11.96
7 -^-v- -13.59
6 -^-v- -16.41
5 -^-v- -21.41
4 -^-v- -27.78
3 -^-v- -267.6
2 -^-v- -381.2
1 -^-v- -506.2
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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 = -169.8763061433 Hartrees
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