Oxalylchloride

Cl3O6
\ //
C1 - C2
// \
O4Cl5
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

C1 charge= 0.382
C2 charge= 0.383
CL3 charge=-0.054
O4 charge=-0.328
CL5 charge=-0.055
O6 charge=-0.328
with a dipole moment of 0.01238 Debye

Bond Lengths:

between C1 and C2: distance=1.565 ang___ between C1 and CL3: distance=1.785 ang___
between C1 and O4: distance=1.198 ang___ between C1 and CL5: distance=2.773 ang___
between C2 and CL3: distance=2.773 ang___ between C2 and CL5: distance=1.785 ang___
between C2 and O6: distance=1.199 ang___

Bond Angles:

for CL3-C1-C2: angle=111.5 deg___ for O4-C1-C2: angle=125.1 deg___
for CL5-C2-C1: angle=111.5 deg___ for O6-C2-C1: angle=125.1 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.682___ between C1 and CL3: order=1.083___
between C1 and O4: order=1.974___ between C1 and CL5: order=-0.114___
between C2 and CL3: order=-0.114___ between C2 and CL5: order=1.083___
between C2 and O6: order=1.974___

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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 C1-C2 with 1.9793 electrons
__has 50.00% C 1 character in a sp1.88 hybrid
__has 50.00% C 2 character in a sp1.88 hybrid

2. A bonding orbital for C1-Cl3 with 1.9836 electrons
__has 45.34% C 1 character in a sp2.47 hybrid
__has 54.66% Cl 3 character in a s0.47 p3 hybrid

3. A bonding orbital for C1-O4 with 1.9983 electrons
__has 34.66% C 1 character in a sp1.69 hybrid
__has 65.34% O 4 character in a sp1.34 hybrid

4. A bonding orbital for C1-O4 with 1.9862 electrons
__has 33.82% C 1 character in a p-pi orbital ( 99.50% p 0.50% d)
__has 66.18% O 4 character in a p-pi orbital ( 99.76% p 0.24% d)

5. A bonding orbital for C2-Cl5 with 1.9836 electrons
__has 45.34% C 2 character in a sp2.47 hybrid
__has 54.66% Cl 5 character in a s0.47 p3 hybrid

6. A bonding orbital for C2-O6 with 1.9983 electrons
__has 34.66% C 2 character in a sp1.69 hybrid
__has 65.34% O 6 character in a sp1.34 hybrid

7. A bonding orbital for C2-O6 with 1.9862 electrons
__has 33.82% C 2 character in a p-pi orbital ( 99.50% p 0.50% d)
__has 66.18% O 6 character in a p-pi orbital ( 99.76% p 0.24% d)

22. A lone pair orbital for Cl3 with 1.9941 electrons
__made from a sp0.15 hybrid

23. A lone pair orbital for Cl3 with 1.9715 electrons
__made from a p3 hybrid

24. A lone pair orbital for Cl3 with 1.9194 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)

25. A lone pair orbital for O4 with 1.9783 electrons
__made from a sp0.74 hybrid

26. A lone pair orbital for O4 with 1.8468 electrons
__made from a p3 hybrid

27. A lone pair orbital for Cl5 with 1.9941 electrons
__made from a sp0.15 hybrid

28. A lone pair orbital for Cl5 with 1.9715 electrons
__made from a p3 hybrid

29. A lone pair orbital for Cl5 with 1.9194 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)

30. A lone pair orbital for O6 with 1.9783 electrons
__made from a sp0.74 hybrid

31. A lone pair orbital for O6 with 1.8469 electrons
__made from a p3 hybrid

152. A antibonding orbital for C1-C2 with 0.1366 electrons
__has 50.00% C 1 character in a sp1.88 hybrid
__has 50.00% C 2 character in a sp1.88 hybrid

153. A antibonding orbital for C1-Cl3 with 0.1115 electrons
__has 54.66% C 1 character in a sp2.47 hybrid
__has 45.34% Cl 3 character in a s0.47 p3 hybrid

156. A antibonding orbital for C2-Cl5 with 0.1115 electrons
__has 54.66% C 2 character in a sp2.47 hybrid
__has 45.34% Cl 5 character in a s0.47 p3 hybrid

-With core pairs on: C 1 C 2 Cl 3 Cl 3 Cl 3 Cl 3 Cl 3 O 4 Cl 5 Cl 5 Cl 5 Cl 5 Cl 5 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 the second bonding donor orbital, 4, for C1-O4 with the second antibonding acceptor orbital, 158, for C2-O6 is 24.3 kJ/mol.

The interaction of the second bonding donor orbital, 7, for C2-O6 with the second antibonding acceptor orbital, 155, for C1-O4 is 24.3 kJ/mol.

The interaction of the second lone pair donor orbital, 23, for Cl3 with the antibonding acceptor orbital, 152, for C1-C2 is 23.6 kJ/mol.

The interaction of the second lone pair donor orbital, 23, for Cl3 with the antibonding acceptor orbital, 154, for C1-O4 is 30.0 kJ/mol.

The interaction of the third lone pair donor orbital, 24, for Cl3 with the second antibonding acceptor orbital, 155, for C1-O4 is 116. kJ/mol.

The interaction of the second lone pair donor orbital, 26, for O4 with the antibonding acceptor orbital, 152, for C1-C2 is 142. kJ/mol.

The interaction of the second lone pair donor orbital, 26, for O4 with the antibonding acceptor orbital, 153, for C1-Cl3 is 205. kJ/mol.

The interaction of the second lone pair donor orbital, 28, for Cl5 with the antibonding acceptor orbital, 152, for C1-C2 is 23.6 kJ/mol.

The interaction of the second lone pair donor orbital, 28, for Cl5 with the antibonding acceptor orbital, 157, for C2-O6 is 30.0 kJ/mol.

The interaction of the third lone pair donor orbital, 29, for Cl5 with the second antibonding acceptor orbital, 158, for C2-O6 is 116. kJ/mol.

The interaction of the second lone pair donor orbital, 31, for O6 with the antibonding acceptor orbital, 152, for C1-C2 is 142. kJ/mol.

The interaction of the second lone pair donor orbital, 31, for O6 with the antibonding acceptor orbital, 156, for C2-Cl5 is 205. 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.

35 ----- -0.384


34 ----- -1.772

33 ----- -2.135


32 ----- -4.976


31 -^-v- -7.750

30 -^-v- -8.614

29 -^-v- -8.880
28 -^-v- -8.897

27 -^-v- -9.071

26 -^-v- -9.328


25 -^-v- -11.44

24 -^-v- -12.16

23 -^-v- -12.83
22 -^-v- -12.92

21 -^-v- -13.36

20 -^-v- -14.31


19 -^-v- -17.80


18 -^-v- -22.27
17 -^-v- -22.29


16 -^-v- -28.20

15 -^-v- -28.54


14 -^-v- -191.3 13 -^-v- -191.3

12 -^-v- -191.4 11 -^-v- -191.4

10 -^-v- -191.8 9 -^-v- -191.8


8 -^-v- -249.8 7 -^-v- -249.8


6 -^-v- -271.6 5 -^-v- -271.6


4 -^-v- -508.5 3 -^-v- -508.5


2 -^-v- -2731. 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 = -1147.2257622110 Hartrees

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