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 N1-O2 with 1.9945 electrons
__has 38.67% N 1 character in a s0.67 p3 hybrid
__has 61.33% O 2 character in a s0.94 p3 hybrid
2. A bonding orbital for N1-O2 with 1.9966 electrons
__has 38.78% N 1 character in a p-pi orbital ( 99.65% p 0.35% d)
__has 61.22% O 2 character in a p-pi orbital ( 99.86% p 0.14% d)
3. A bonding orbital for N1-Cl3 with 1.9842 electrons
__has 53.65% N 1 character in a s0.47 p3 hybrid
__has 46.35% Cl 3 character in a s0.30 p3 hybrid
4. A bonding orbital for O2-O4 with 1.9878 electrons
__has 65.28% O 2 character in a sp2.91 hybrid
__has 34.72% O 4 character in a s0.33 p3 hybrid
13. A lone pair orbital for N1 with 1.9981 electrons
__made from a sp0.45 hybrid
14. A lone pair orbital for O2 with 1.9941 electrons
__made from a sp0.95 hybrid
15. A lone pair orbital for Cl3 with 1.9993 electrons
__made from a sp0.12 hybrid
16. A lone pair orbital for Cl3 with 1.9814 electrons
__made from a s0.08 p3 hybrid
17. A lone pair orbital for Cl3 with 1.9293 electrons
__made from a p-pi orbital ( 99.97% p)
18. A lone pair orbital for O4 with 1.9983 electrons
__made from a sp0.22 hybrid
19. A lone pair orbital for O4 with 1.9618 electrons
__made from a s0.29 p3 hybrid
20. A lone pair orbital for O4 with 1.6711 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)
101. A antibonding orbital for N1-O2 with 0.3942 electrons
__has 61.22% N 1 character in a p-pi orbital ( 99.65% p 0.35% d)
__has 38.78% O 2 character in a p-pi orbital ( 99.86% p 0.14% d)
-With core pairs on: N 1 O 2 Cl 3 Cl 3 Cl 3 Cl 3 Cl 3 O 4 -
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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, 3, for N1-Cl3 with
the antibonding acceptor orbital, 103, for O2-O4 is 21.4 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for Cl3 with
the antibonding acceptor orbital, 100, for N1-O2 is 29.3 kJ/mol.
The interaction of the third lone pair donor orbital, 17, for Cl3 with
the second antibonding acceptor orbital, 101, for N1-O2 is 103. kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O4 with
the antibonding acceptor orbital, 100, for N1-O2 is 59.9 kJ/mol.
The interaction of the third lone pair donor orbital, 20, for O4 with
the second antibonding acceptor orbital, 101, for N1-O2 is 502. 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.
24 ----- 1.549
23 ----- 0.106
22 ----- -3.344
21 ----- -5.530
20 -^-v- -7.309
19 -^-v- -7.602
18 -^-v- -8.821
17 -^-v- -10.08
16 -^-v- -10.09
15 -^-v- -13.80
14 -^-v- -14.04
13 -^-v- -14.59
12 -^-v- -17.53
11 -^-v- -22.14
10 -^-v- -25.80
9 -^-v- -32.47
8 -^-v- -192.1
7 -^-v- -192.1
6 -^-v- -192.6
5 -^-v- -250.6
4 -^-v- -382.0
3 -^-v- -508.7
2 -^-v- -512.9
1 -^-v- -2731.
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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 = -665.3083846273 Hartrees
*Note: Compare with the lower energy isomer
ClNO2, nitrylchloride
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