1-chloro-2-propene, allyl chloride, CH2=CHCH2Cl

H5
\
H8C3 - H4
\ //
C1 - C2
/ | \
Cl7H9H6
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=-0.263
C2 charge= 0.028
C3 charge=-0.494
H4 charge= 0.196
H5 charge= 0.219
H6 charge= 0.129
CL7 charge=-0.156
H8 charge= 0.179
H9 charge= 0.162
with a dipole moment of 2.15070 Debye

Bond Lengths:

between C1 and C2: distance=1.495 ang___ between C1 and C3: distance=2.499 ang___
between C1 and CL7: distance=1.850 ang___ between C1 and H8: distance=1.101 ang___
between C1 and H9: distance=1.103 ang___ between C2 and C3: distance=1.344 ang___
between C2 and H5: distance=2.133 ang___ between C2 and H6: distance=1.099 ang___
between C2 and CL7: distance=2.759 ang___ between C2 and H8: distance=2.169 ang___
between C3 and H4: distance=1.095 ang___ between C3 and H5: distance=1.097 ang___

Bond Angles:

for C3-C2-C1: angle=123.3 deg___ for H4-C3-C2: angle=121.6 deg___
for H5-C3-C2: angle=121.5 deg___ for H6-C2-C1: angle=115.9 deg___
for CL7-C1-C2: angle=110.6 deg___ for H8-C1-C2: angle=112.4 deg___
for H9-C1-C2: angle=112.2 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.875___ between C1 and C3: order=0.150___
between C1 and CL7: order=0.827___ between C1 and H8: order=0.985___
between C1 and H9: order=0.965___ between C2 and C3: order=1.840___
between C2 and H5: order=-0.055___ between C2 and H6: order=0.909___
between C2 and CL7: order=-0.104___ between C2 and H8: order=-0.083___
between C3 and H4: order=0.965___ between C3 and H5: order=0.985___

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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-C2 with 1.9911 electrons
__has 51.46% C 1 character in a sp2.08 hybrid
__has 48.54% C 2 character in a sp2.12 hybrid

2. A bonding orbital for C1-Cl7 with 1.9869 electrons
__has 42.14% C 1 character in a s0.66 p3 hybrid
__has 57.86% Cl 7 character in a s0.50 p3 hybrid

3. A bonding orbital for C1-H8 with 1.9901 electrons
__has 60.38% C 1 character in a sp2.96 hybrid
__has 39.62% H 8 character in a s orbital

4. A bonding orbital for C1-H9 with 1.9851 electrons
__has 60.55% C 1 character in a s0.97 p3 hybrid
__has 39.45% H 9 character in a s orbital

5. A bonding orbital for C2-C3 with 1.9927 electrons
__has 51.13% C 2 character in a sp1.56 hybrid
__has 48.87% C 3 character in a sp1.53 hybrid

6. A bonding orbital for C2-C3 with 1.9666 electrons
__has 50.27% C 2 character in a p3 hybrid
__has 49.73% C 3 character in a p3 hybrid

7. A bonding orbital for C2-H6 with 1.9794 electrons
__has 60.09% C 2 character in a sp2.50 hybrid
__has 39.91% H 6 character in a s orbital

8. A bonding orbital for C3-H4 with 1.9869 electrons
__has 59.61% C 3 character in a sp2.32 hybrid
__has 40.39% H 4 character in a s orbital

9. A bonding orbital for C3-H5 with 1.9874 electrons
__has 59.15% C 3 character in a sp2.34 hybrid
__has 40.85% H 5 character in a s orbital

18. A lone pair orbital for Cl7 with 1.9978 electrons
__made from a sp0.18 hybrid

19. A lone pair orbital for Cl7 with 1.9856 electrons
__made from a p3 hybrid

20. A lone pair orbital for Cl7 with 1.9812 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 C 3 Cl 7 Cl 7 Cl 7 Cl 7 Cl 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 the second bonding donor orbital, 6, for C2-C3 with the antibonding acceptor orbital, 126, for C1-Cl7 is 37.9 kJ/mol.

The interaction of bonding donor orbital, 7, for C2-H6 with the antibonding acceptor orbital, 133, for C3-H5 is 22.6 kJ/mol.

The interaction of bonding donor orbital, 8, for C3-H4 with the antibonding acceptor orbital, 125, for C1-C2 is 29.4 kJ/mol.

The interaction of bonding donor orbital, 9, for C3-H5 with the antibonding acceptor orbital, 131, for C2-H6 is 26.3 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 ----- 1.922

23 ----- 1.666


22 ----- -0.257


21 ----- -1.944


20 -^-v- -6.905

19 -^-v- -7.076

18 -^-v- -7.359


17 -^-v- -9.055

16 -^-v- -9.878

15 -^-v- -10.75

14 -^-v- -11.19

13 -^-v- -12.13


12 -^-v- -14.07


11 -^-v- -16.65


10 -^-v- -19.29


9 -^-v- -21.23


8 -^-v- -189.8
7 -^-v- -189.8

6 -^-v- -190.2


5 -^-v- -248.2


4 -^-v- -266.7

3 -^-v- -267.0


2 -^-v- -268.1


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 = -577.5823015705 Hartrees

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