cis-1-chloro-1-propene, C3H5Cl

H6
/
H5 - C4 - H7
\
C3 - H8
//
Cl1 - C2
\
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

CL1 charge=-0.048
C2 charge=-0.344
C3 charge= 0.020
C4 charge=-0.203
H5 charge= 0.095
H6 charge= 0.083
H7 charge= 0.082
H8 charge= 0.095
H9 charge= 0.218
with a dipole moment of 1.77735 Debye

Bond Lengths:

between CL1 and C2: distance=1.768 ang___ between CL1 and C3: distance=2.751 ang___
between CL1 and C4: distance=3.254 ang___ between C2 and C3: distance=1.340 ang___
between C2 and H9: distance=1.093 ang___ between C3 and C4: distance=1.501 ang___
between C3 and H5: distance=2.165 ang___ between C3 and H8: distance=1.100 ang___
between C4 and H5: distance=1.102 ang___ between C4 and H6: distance=1.105 ang___
between C4 and H7: distance=1.106 ang___

Bond Angles:

for C3-C2-CL1: angle=123.9 deg___ for C4-C3-C2: angle=127.5 deg___
for H5-C4-C3: angle=111.6 deg___ for H6-C4-C3: angle=110.6 deg___
for H7-C4-C3: angle=110.6 deg___ for H8-C3-C2: angle=114.9 deg___
for H9-C2-CL1: angle=111.9 deg___

Top of page.

Bond Orders (Mulliken):

between CL1 and C2: order=0.734___ between CL1 and C3: order=0.069___
between CL1 and C4: order=-0.055___ between C2 and C3: order=1.906___
between C2 and H9: order=0.916___ between C3 and C4: order=0.833___
between C3 and H5: order=-0.104___ between C3 and H8: order=0.904___
between C4 and H5: order=1.029___ between C4 and H6: order=0.965___
between C4 and H7: order=0.965___

Top of page.

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 Cl1-C2 with 1.9913 electrons
__has 56.42% Cl 1 character in a s0.63 p3 hybrid
__has 43.58% C 2 character in a s0.97 p3 hybrid

2. A bonding orbital for C2-C3 with 1.9934 electrons
__has 49.77% C 2 character in a sp1.31 hybrid
__has 50.23% C 3 character in a sp1.59 hybrid

3. A bonding orbital for C2-C3 with 1.9822 electrons
__has 53.61% C 2 character in a p-pi orbital ( 99.88% p 0.12% d)
__has 46.39% C 3 character in a p-pi orbital ( 99.83% p 0.17% d)

4. A bonding orbital for C2-H9 with 1.9840 electrons
__has 60.85% C 2 character in a sp2.08 hybrid
__has 39.15% H 9 character in a s orbital

5. A bonding orbital for C3-C4 with 1.9901 electrons
__has 50.57% C 3 character in a sp1.91 hybrid
__has 49.43% C 4 character in a sp2.40 hybrid

6. A bonding orbital for C3-H8 with 1.9693 electrons
__has 59.78% C 3 character in a sp2.66 hybrid
__has 40.22% H 8 character in a s orbital

7. A bonding orbital for C4-H5 with 1.9911 electrons
__has 60.60% C 4 character in a s0.97 p3 hybrid
__has 39.40% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9829 electrons
__has 59.90% C 4 character in a s0.90 p3 hybrid
__has 40.10% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 1.9829 electrons
__has 59.90% C 4 character in a s0.90 p3 hybrid
__has 40.10% H 7 character in a s orbital

18. A lone pair orbital for Cl1 with 1.9949 electrons
__made from a sp0.21 hybrid

19. A lone pair orbital for Cl1 with 1.9767 electrons
__made from a p3 hybrid

20. A lone pair orbital for Cl1 with 1.9544 electrons
__made from a p-pi orbital ( 99.98% p)

-With core pairs on:Cl 1 Cl 1 Cl 1 Cl 1 Cl 1 C 2 C 3 C 4 -

Top of page.

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, 4, for C2-H9 with the antibonding acceptor orbital, 129, for C3-C4 is 30.6 kJ/mol.

The interaction of bonding donor orbital, 6, for C3-H8 with the antibonding acceptor orbital, 125, for Cl1-C2 is 48.9 kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H6 with the second antibonding acceptor orbital, 127, for C2-C3 is 22.8 kJ/mol.

The interaction of bonding donor orbital, 9, for C4-H7 with the second antibonding acceptor orbital, 127, for C2-C3 is 22.8 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for Cl1 with the antibonding acceptor orbital, 126, for C2-C3 is 25.8 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for Cl1 with the antibonding acceptor orbital, 128, for C2-H9 is 25.1 kJ/mol.

The interaction of the third lone pair donor orbital, 20, for Cl1 with the second antibonding acceptor orbital, 127, for C2-C3 is 73.8 kJ/mol.

Top of page.

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 ----- 2.026
23 ----- 1.841


22 ----- -0.213

21 ----- -1.162


20 -^-v- -6.190


19 -^-v- -7.469


18 -^-v- -8.676

17 -^-v- -8.909

16 -^-v- -9.551

15 -^-v- -10.34

14 -^-v- -10.92


13 -^-v- -12.20


12 -^-v- -13.55


11 -^-v- -16.90


10 -^-v- -19.20


9 -^-v- -21.57


8 -^-v- -190.1
7 -^-v- -190.2

6 -^-v- -190.6


5 -^-v- -248.6


4 -^-v- -266.4

3 -^-v- -266.8


2 -^-v- -267.8


1 -^-v- -2729.

Top of page.

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 = -577.5870895479 Hartrees

Top of page.

-> Return to Molecular Structure Page. -> Return to Chemistry Home Page