## 2-chloro-1-propene, C3H5Cl

 Cl8 H7 H6 \ | / C3 - C4 // \ H1 - C2 H5 \ H9
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

H1 charge= 0.215
C2 charge=-0.561
C3 charge= 0.235
C4 charge=-0.449
H5 charge= 0.161
H6 charge= 0.148
H7 charge= 0.150
CL8 charge=-0.128
H9 charge= 0.227
with a dipole moment of 1.77603 Debye

## Bond Lengths:

between H1 and C2: distance=1.093 ang___ between C2 and C3: distance=1.340 ang___
between C2 and C4: distance=2.548 ang___ between C2 and CL8: distance=2.707 ang___
between C2 and H9: distance=1.096 ang___ between C3 and C4: distance=1.499 ang___
between C3 and H5: distance=2.151 ang___ between C3 and CL8: distance=1.786 ang___
between C4 and H5: distance=1.103 ang___ between C4 and H6: distance=1.105 ang___
between C4 and H7: distance=1.105 ang___

## Bond Angles:

for C3-C2-H1: angle=122.2 deg___ for C4-C3-C2: angle=127.5 deg___
for H5-C4-C3: angle=110.5 deg___ for H6-C4-C3: angle=110.6 deg___
for H7-C4-C3: angle=110.6 deg___ for CL8-C3-C2: angle=119.3 deg___
for H9-C2-H1: angle=118.1 deg___

## Bond Orders (Mulliken):

between H1 and C2: order=0.968___ between C2 and C3: order=1.874___
between C2 and C4: order=0.218___ between C2 and CL8: order=0.144___
between C2 and H9: order=0.949___ between C3 and C4: order=0.731___
between C3 and H5: order=-0.101___ between C3 and CL8: order=0.528___
between C4 and H5: order=1.022___ between C4 and H6: order=0.959___
between C4 and H7: order=0.958___

## 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 H1-C2 with 1.9846 electrons
__has 39.65% H 1 character in a s orbital
__has 60.35% C 2 character in a sp2.25 hybrid

2. A bonding orbital for C2-C3 with 1.9939 electrons
__has 48.70% C 2 character in a sp1.53 hybrid
__has 51.30% C 3 character in a sp1.36 hybrid

3. A bonding orbital for C2-C3 with 1.9790 electrons
__has 50.00% C 2 character in a p-pi orbital ( 99.82% p 0.18% d)
__has 50.00% C 3 character in a p-pi orbital ( 99.86% p 0.14% d)

4. A bonding orbital for C2-H9 with 1.9769 electrons
__has 59.68% C 2 character in a sp2.34 hybrid
__has 40.32% H 9 character in a s orbital

5. A bonding orbital for C3-C4 with 1.9903 electrons
__has 50.96% C 3 character in a sp1.79 hybrid
__has 49.04% C 4 character in a sp2.38 hybrid

6. A bonding orbital for C3-Cl8 with 1.9864 electrons
__has 43.47% C 3 character in a s0.85 p3 hybrid
__has 56.53% Cl 8 character in a s0.63 p3 hybrid

7. A bonding orbital for C4-H5 with 1.9834 electrons
__has 59.91% C 4 character in a s0.94 p3 hybrid
__has 40.09% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9827 electrons
__has 60.35% C 4 character in a s0.91 p3 hybrid
__has 39.65% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 1.9824 electrons
__has 60.34% C 4 character in a s0.91 p3 hybrid
__has 39.66% H 7 character in a s orbital

18. A lone pair orbital for Cl8 with 1.9910 electrons

19. A lone pair orbital for Cl8 with 1.9775 electrons

20. A lone pair orbital for Cl8 with 1.9533 electrons
__made from a p-pi orbital ( 99.98% p)

-With core pairs on: C 2 C 3 C 4 Cl 8 Cl 8 Cl 8 Cl 8 Cl 8 -

#### 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, 1, for H1-C2 with the antibonding acceptor orbital, 129, for C3-C4 is 36.4 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-H9 with the antibonding acceptor orbital, 130, for C3-Cl8 is 49.2 kJ/mol.

The interaction of bonding donor orbital, 7, for C4-H5 with the antibonding acceptor orbital, 130, for C3-Cl8 is 35.1 kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H6 with the second antibonding acceptor orbital, 127, for C2-C3 is 21.8 kJ/mol.

The interaction of bonding donor orbital, 9, for C4-H7 with the second antibonding acceptor orbital, 127, for C2-C3 is 22.6 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for Cl8 with the antibonding acceptor orbital, 126, for C2-C3 is 20.5 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for Cl8 with the antibonding acceptor orbital, 129, for C3-C4 is 22.1 kJ/mol.

The interaction of the third lone pair donor orbital, 20, for Cl8 with the second antibonding acceptor orbital, 127, for C2-C3 is 76.7 kJ/mol.

## 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 ----- 1.979
23 ----- 1.807

22 ----- -0.379

21 ----- -1.285

20 -^-v- -6.314

19 -^-v- -7.448

18 -^-v- -8.357

17 -^-v- -9.213

16 -^-v- -9.589

15 -^-v- -10.71

14 -^-v- -11.18

13 -^-v- -11.80

12 -^-v- -13.44

11 -^-v- -17.36

10 -^-v- -18.87

9 -^-v- -21.69

8 -^-v- -190.1
7 -^-v- -190.1

6 -^-v- -190.5

5 -^-v- -248.5

4 -^-v- -266.4

3 -^-v- -266.6

2 -^-v- -268.3

1 -^-v- -2729.

## 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 = -577.5885652334 Hartrees