CH3COCl, Acetylchloride

H3O7
\ //
H5 - C1 - C2
/ \
H4Cl6
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=-0.517
C2 charge= 0.545
H3 charge= 0.192
H4 charge= 0.192
H5 charge= 0.154
CL6 charge=-0.189
O7 charge=-0.377
with a dipole moment of 3.06053 Debye

Bond Lengths:

between C1 and C2: distance=1.505 ang___ between C1 and H3: distance=1.105 ang___
between C1 and H4: distance=1.104 ang___ between C1 and H5: distance=1.097 ang___
between C1 and CL6: distance=2.807 ang___ between C1 and O7: distance=2.425 ang___
between C2 and CL6: distance=1.848 ang___ between C2 and O7: distance=1.200 ang___

Bond Angles:

for H3-C1-C2: angle=107.8 deg___ for H4-C1-C2: angle=108.0 deg___
for H5-C1-C2: angle=112.9 deg___ for CL6-C2-C1: angle=113.2 deg___
for O7-C2-C1: angle=126.9 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.817___ between C1 and H3: order=0.970___
between C1 and H4: order=0.970___ between C1 and H5: order=0.968___
between C1 and CL6: order=-0.100___ between C1 and O7: order=-0.050___
between C2 and CL6: order=0.959___ between C2 and O7: order=1.934___

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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 1.9900 electrons
__has 49.66% C 1 character in a sp2.80 hybrid
__has 50.34% C 2 character in a sp1.42 hybrid

2. A bonding orbital for C1-H3 with 1.9748 electrons
__has 61.39% C 1 character in a s0.95 p3 hybrid
__has 38.61% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9753 electrons
__has 61.39% C 1 character in a s0.95 p3 hybrid
__has 38.61% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9911 electrons
__has 61.25% C 1 character in a sp2.88 hybrid
__has 38.75% H 5 character in a s orbital

5. A bonding orbital for C2-Cl6 with 1.9868 electrons
__has 40.74% C 2 character in a s0.92 p3 hybrid
__has 59.26% Cl 6 character in a s0.46 p3 hybrid

6. A bonding orbital for C2-O7 with 1.9980 electrons
__has 33.82% C 2 character in a sp1.80 hybrid
__has 66.18% O 7 character in a sp1.29 hybrid

7. A bonding orbital for C2-O7 with 1.9958 electrons
__has 30.23% C 2 character in a p-pi orbital ( 99.43% p 0.56% d)
__has 69.77% O 7 character in a p-pi orbital ( 99.77% p 0.23% d)

16. A lone pair orbital for Cl6 with 1.9933 electrons
__made from a sp0.16 hybrid

17. A lone pair orbital for Cl6 with 1.9820 electrons
__made from a p3 hybrid

18. A lone pair orbital for Cl6 with 1.9363 electrons
__made from a p-pi orbital ( 99.95% p)

19. A lone pair orbital for O7 with 1.9749 electrons
__made from a sp0.78 hybrid

20. A lone pair orbital for O7 with 1.8368 electrons
__made from a p3 hybrid

119. A antibonding orbital for C2-Cl6 with 0.1432 electrons
__has 59.26% C 2 character in a s0.92 p3 hybrid
__has 40.74% Cl 6 character in a s0.46 p3 hybrid

-With core pairs on: C 1 C 2 Cl 6 Cl 6 Cl 6 Cl 6 Cl 6 O 7 -

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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 C1-H3 with the second antibonding acceptor orbital, 121, for C2-O7 is 29.9 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-H4 with the second antibonding acceptor orbital, 121, for C2-O7 is 28.6 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H5 with the antibonding acceptor orbital, 120, for C2-O7 is 24.3 kJ/mol.

The interaction of the second lone pair donor orbital, 17, for Cl6 with the antibonding acceptor orbital, 120, for C2-O7 is 28.5 kJ/mol.

The interaction of the third lone pair donor orbital, 18, for Cl6 with the second antibonding acceptor orbital, 121, for C2-O7 is 90.5 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O7 with the antibonding acceptor orbital, 115, for C1-C2 is 88.1 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O7 with the antibonding acceptor orbital, 119, for C2-Cl6 is 272. 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 ----- 2.107

23 ----- 1.612


22 ----- -0.995


21 ----- -2.632


20 -^-v- -7.321

19 -^-v- -7.844

18 -^-v- -8.028


17 -^-v- -9.978

16 -^-v- -10.44


15 -^-v- -11.75

14 -^-v- -12.01

13 -^-v- -12.31


12 -^-v- -13.97


11 -^-v- -19.05


10 -^-v- -21.10


9 -^-v- -27.39


8 -^-v- -190.3
7 -^-v- -190.3

6 -^-v- -190.6


5 -^-v- -248.7


4 -^-v- -267.4


3 -^-v- -270.6


2 -^-v- -507.5


1 -^-v- -2729.

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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 = -613.5509459324 Hartrees

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