trans-1-chloro-1-propene, C3H5Cl

H8H7H6
\ | /
C3 - C4
// \
Cl1 - C2H5
\
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=-0.067
C2 charge=-0.372
C3 charge= 0.082
C4 charge=-0.378
H5 charge= 0.124
H6 charge= 0.123
H7 charge= 0.123
H8 charge= 0.113
H9 charge= 0.250
with a dipole moment of 2.08966 Debye

Bond Lengths:

between CL1 and C2: distance=1.764 ang___ between C2 and C3: distance=1.339 ang___
between C2 and C4: distance=2.504 ang___ between C2 and H9: distance=1.095 ang___
between C3 and C4: distance=1.507 ang___ between C3 and H5: distance=2.176 ang___
between C3 and H8: distance=1.099 ang___ between C4 and H5: distance=1.103 ang___
between C4 and H6: distance=1.106 ang___ between C4 and H7: distance=1.106 ang___

Bond Angles:

for C3-C2-CL1: angle=123.1 deg___ for C4-C3-C2: angle=123.0 deg___
for H5-C4-C3: angle=111.9 deg___ for H6-C4-C3: angle=110.8 deg___
for H7-C4-C3: angle=110.6 deg___ for H8-C3-C2: angle=119.2 deg___
for H9-C2-CL1: angle=112.3 deg___

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Bond Orders (Mulliken):

between CL1 and C2: order=0.836___ between C2 and C3: order=1.868___
between C2 and C4: order=0.088___ between C2 and H9: order=0.921___
between C3 and C4: order=0.809___ between C3 and H5: order=-0.088___
between C3 and H8: order=0.915___ between C4 and H5: order=1.017___
between C4 and H6: order=0.972___ between C4 and H7: order=0.972___

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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 Cl1-C2 with 1.9903 electrons
__has 55.96% Cl 1 character in a s0.63 p3 hybrid
__has 44.04% C 2 character in a s0.99 p3 hybrid

2. A bonding orbital for C2-C3 with 1.9937 electrons
__has 49.81% C 2 character in a sp1.31 hybrid
__has 50.19% C 3 character in a sp1.59 hybrid

3. A bonding orbital for C2-C3 with 1.9807 electrons
__has 53.65% C 2 character in a p-pi orbital ( 99.87% p 0.13% d)
__has 46.35% C 3 character in a p-pi orbital ( 99.82% p 0.18% d)

4. A bonding orbital for C2-H9 with 1.9852 electrons
__has 60.64% C 2 character in a sp2.11 hybrid
__has 39.36% H 9 character in a s orbital

5. A bonding orbital for C3-C4 with 1.9841 electrons
__has 50.40% C 3 character in a sp1.99 hybrid
__has 49.60% C 4 character in a sp2.38 hybrid

6. A bonding orbital for C3-H8 with 1.9794 electrons
__has 60.17% C 3 character in a sp2.53 hybrid
__has 39.83% H 8 character in a s orbital

7. A bonding orbital for C4-H5 with 1.9915 electrons
__has 59.65% C 4 character in a s0.95 p3 hybrid
__has 40.35% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9841 electrons
__has 59.86% C 4 character in a s0.91 p3 hybrid
__has 40.14% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 1.9840 electrons
__has 59.86% C 4 character in a s0.90 p3 hybrid
__has 40.14% 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 1.9774 electrons
__made from a p3 hybrid

20. A lone pair orbital for Cl1 with 1.9552 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 -

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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, 4, for C2-H9 with the antibonding acceptor orbital, 130, for C3-H8 is 21.8 kJ/mol.

The interaction of bonding donor orbital, 5, for C3-C4 with the antibonding acceptor orbital, 125, for Cl1-C2 is 27.1 kJ/mol.

The interaction of bonding donor orbital, 6, for C3-H8 with the antibonding acceptor orbital, 128, for C2-H9 is 25.8 kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H6 with the second antibonding acceptor orbital, 127, for C2-C3 is 20.9 kJ/mol.

The interaction of bonding donor orbital, 9, for C4-H7 with the second antibonding acceptor orbital, 127, for C2-C3 is 21.2 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for Cl1 with the antibonding acceptor orbital, 126, for C2-C3 is 24.5 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for Cl1 with the antibonding acceptor orbital, 128, for C2-H9 is 26.4 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 71.6 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 ----- 1.959

23 ----- 1.555


22 ----- -0.204


21 ----- -1.231


20 -^-v- -6.131


19 -^-v- -7.446


18 -^-v- -8.697

17 -^-v- -9.042

16 -^-v- -9.504

15 -^-v- -10.40

14 -^-v- -11.17

13 -^-v- -11.71


12 -^-v- -13.97


11 -^-v- -16.67


10 -^-v- -19.32


9 -^-v- -21.54


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

6 -^-v- -190.5


5 -^-v- -248.6


4 -^-v- -266.5

3 -^-v- -266.8


2 -^-v- -267.8


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 = -577.5861877629 Hartrees

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