CH3ClO, CH3Cl->O

H3
|
C1 - Cl2
/ | \
H4H5O6
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=-0.473
CL2 charge= 0.315
H3 charge= 0.200
H4 charge= 0.213
H5 charge= 0.213
O6 charge=-0.469
with a dipole moment of 4.85153 Debye

Bond Lengths:

between C1 and CL2: distance=1.872 ang___ between C1 and H3: distance=1.102 ang___
between C1 and H4: distance=1.098 ang___ between C1 and H5: distance=1.099 ang___
between C1 and O6: distance=2.847 ang___ between CL2 and O6: distance=1.614 ang___

Bond Angles:

for H3-C1-CL2: angle=105.6 deg___ for H4-C1-CL2: angle=106.1 deg___
for H5-C1-CL2: angle=106.1 deg___ for O6-CL2-C1: angle=109.2 deg___

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Bond Orders (Mulliken):

between C1 and CL2: order=0.772___ between C1 and H3: order=0.947___
between C1 and H4: order=0.940___ between C1 and H5: order=0.940___
between C1 and O6: order=0.061___ between CL2 and O6: order=0.808___

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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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-Cl2 with 1.9919 electrons
__has 39.75% C 1 character in a s0.61 p3 hybrid
__has 60.25% Cl 2 character in a s0.52 p3 hybrid

2. A bonding orbital for C1-H3 with 1.9934 electrons
__has 60.42% C 1 character in a sp2.63 hybrid
__has 39.58% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9965 electrons
__has 61.13% C 1 character in a sp2.57 hybrid
__has 38.87% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9965 electrons
__has 61.15% C 1 character in a sp2.58 hybrid
__has 38.85% H 5 character in a s orbital

5. A bonding orbital for Cl2-O6 with 1.9943 electrons
__has 57.43% Cl 2 character in a s0.68 p3 hybrid
__has 42.57% O 6 character in a s0.23 p3 hybrid

13. A lone pair orbital for Cl2 with 1.9971 electrons
__made from a sp0.48 hybrid

14. A lone pair orbital for Cl2 with 1.9831 electrons
__made from a p-pi orbital ( 99.96% p)

15. A lone pair orbital for O6 with 1.9987 electrons
__made from a sp0.09 hybrid

16. A lone pair orbital for O6 with 1.9865 electrons
__made from a p-pi orbital ( 99.96% p)

17. A lone pair orbital for O6 with 1.9364 electrons
__made from a s0.06 p3 hybrid

-With core pairs on: C 1 Cl 2 Cl 2 Cl 2 Cl 2 Cl 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 the third lone pair donor orbital, 17, for O6 with the antibonding acceptor orbital, 93, for C1-Cl2 is 68.8 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.

21 ----- 2.810

20 ----- 1.329


19 ----- -1.741

18 ----- -1.965


17 -^-v- -5.083


16 -^-v- -6.195


15 -^-v- -9.613

14 -^-v- -10.30


13 -^-v- -11.80
12 -^-v- -11.86

11 -^-v- -12.00


10 -^-v- -17.20


9 -^-v- -20.34


8 -^-v- -25.65


7 -^-v- -192.8

6 -^-v- -193.1

5 -^-v- -193.3


4 -^-v- -251.4


3 -^-v- -268.3


2 -^-v- -505.9


1 -^-v- -2732.

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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 = -575.2799971735 Hartrees

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