ClNO2, nitrylchloride*

CL3
\
N1 = O2
//
O4
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.

Atomic Charges and Dipole Moment

N1 charge= 0.518
O2 charge=-0.196
CL3 charge=-0.126
O4 charge=-0.196
with a dipole moment of 0.18901 Debye

Bond Lengths:

between N1 and O2: distance=1.206 ang___ between N1 and CL3: distance=1.954 ang___
between N1 and O4: distance=1.205 ang___

Bond Angles:

for CL3-N1-O2: angle=113.3 deg___ for O4-O2-N1: angle=23.29 deg___

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Bond Orders (Mulliken):

between N1 and O2: order=1.527___ between N1 and CL3: order=0.931___
between N1 and O4: order=1.529___

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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 1.9937 electrons
__has 49.99% N 1 character in a sp1.47 hybrid
__has 50.01% O 2 character in a s0.95 p3 hybrid

2. A bonding orbital for N1-Cl3 with 1.9783 electrons
__has 56.79% N 1 character in a s0.76 p3 hybrid
__has 43.21% Cl 3 character in a s0.14 p3 hybrid

3. A bonding orbital for N1-O4 with 1.9938 electrons
__has 49.96% N 1 character in a sp1.47 hybrid
__has 50.04% O 4 character in a s0.95 p3 hybrid

4. A bonding orbital for N1-O4 with 1.9974 electrons
__has 34.17% N 1 character in a p-pi orbital ( 99.61% p 0.39% d)
__has 65.83% O 4 character in a p-pi orbital ( 99.80% p 0.20% d)

13. A lone pair orbital for O2 with 1.9777 electrons
__made from a sp0.34 hybrid

14. A lone pair orbital for O2 with 1.8344 electrons
__made from a s0.05 p3 hybrid

15. A lone pair orbital for O2 with 1.4932 electrons
__made from a p-pi orbital ( 99.82% p 0.18% d)

16. A lone pair orbital for Cl3 with 1.9968 electrons
__made from a s orbital

17. A lone pair orbital for Cl3 with 1.9938 electrons
__made from a p-pi orbital ( 99.99% p)

18. A lone pair orbital for Cl3 with 1.9760 electrons
__made from a p-pi orbital ( 99.98% p)

19. A lone pair orbital for O4 with 1.9777 electrons
__made from a sp0.34 hybrid

20. A lone pair orbital for O4 with 1.8346 electrons
__made from a s0.05 p3 hybrid

101. A antibonding orbital for N1-Cl3 with 0.2777 electrons
__has 43.21% N 1 character in a s0.76 p3 hybrid
__has 56.79% Cl 3 character in a s0.14 p3 hybrid

103. A antibonding orbital for N1-O4 with 0.5174 electrons
__has 65.83% N 1 character in a p-pi orbital ( 99.61% p 0.39% d)
__has 34.17% O 4 character in a p-pi orbital ( 99.80% p 0.20% 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, 2, for N1-Cl3 with the antibonding acceptor orbital, 101, for N1-Cl3 is 22.6 kJ/mol.

The interaction of the second bonding donor orbital, 4, for N1-O4 with the third lone pair acceptor orbital, 15, for O2 is 55.8 kJ/mol.

The interaction of the second bonding donor orbital, 4, for N1-O4 with the second antibonding acceptor orbital, 103, for N1-O4 is 23.6 kJ/mol.

The interaction of lone pair donor orbital, 13, for O2 with the antibonding acceptor orbital, 102, for N1-O4 is 41.9 kJ/mol.

The interaction of the second lone pair donor orbital, 14, for O2 with the antibonding acceptor orbital, 101, for N1-Cl3 is 264. kJ/mol.

The interaction of the second lone pair donor orbital, 14, for O2 with the antibonding acceptor orbital, 102, for N1-O4 is 63.7 kJ/mol.

The interaction of the third lone pair donor orbital, 15, for O2 with the second antibonding acceptor orbital, 103, for N1-O4 is 1221 kJ/mol.

The interaction of the third lone pair donor orbital, 18, for Cl3 with the second antibonding acceptor orbital, 103, for N1-O4 is 35.5 kJ/mol.

The interaction of lone pair donor orbital, 19, for O4 with the antibonding acceptor orbital, 100, for N1-O2 is 41.9 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O4 with the antibonding acceptor orbital, 100, for N1-O2 is 63.8 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O4 with the antibonding acceptor orbital, 101, for N1-Cl3 is 264. 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 ----- 4.715

23 ----- 2.963


22 ----- -4.462

21 ----- -4.723


20 -^-v- -8.024

19 -^-v- -8.497

18 -^-v- -9.157

17 -^-v- -9.583

16 -^-v- -9.870


15 -^-v- -14.50

14 -^-v- -14.98

13 -^-v- -15.17


12 -^-v- -16.89


11 -^-v- -21.46


10 -^-v- -29.11


9 -^-v- -33.03


8 -^-v- -191.0
7 -^-v- -191.0

6 -^-v- -191.5


5 -^-v- -249.5


4 -^-v- -385.7


3 -^-v- -509.8 2 -^-v- -509.8


1 -^-v- -2730.

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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 = -665.4203445062 Hartrees

*Note: Compare with the higher energy isomers ClNOO, nitrosyl chloride peroxide and trans-ClONO

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