1-dehydro-1-chloroethane radical, CH3CH(•)Cl

H3
\
H4 - C1 - C2 - CL6
/ \
H5H7
The multiplicity is 2.

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=-0.202
C2 charge=-0.196
H3 charge= 0.106
H4 charge= 0.098
H5 charge= 0.102
CL6 charge=-0.068
H7 charge= 0.159
with a dipole moment of 1.57973 Debye

Bond Lengths:

between C1 and C2: distance=1.486 ang___ between C1 and H3: distance=1.112 ang___
between C1 and H4: distance=1.104 ang___ between C1 and H5: distance=1.108 ang___
between C2 and CL6: distance=1.745 ang___ between C2 and H7: distance=1.091 ang___

Bond Angles:

for H3-C1-C2: angle=112.4 deg___ for H4-C1-C2: angle=109.9 deg___
for H5-C1-C2: angle=111.9 deg___ for CL6-C2-C1: angle=119.1 deg___
for H7-C2-C1: angle=125.5 deg___

Top of page.

Bond Orders (Mulliken):

between C1 and C2: order=0.888___ between C1 and H3: order=0.965___
between C1 and H4: order=0.969___ between C1 and H5: order=0.976___
between C2 and CL6: order=0.892___ between C2 and H7: order=0.911___

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. The Lewis structure is built for the up and down electrons, separately. Note that the up and down structures can be very different.

Hybridization in the Best Lewis Structure

Down Electrons

1. A bonding orbital for C1-C2 with 0.9981 electrons
__has 48.09% C 1 character in a sp2.48 hybrid
__has 51.91% C 2 character in a sp1.53 hybrid

2. A bonding orbital for C1-H3 with 0.9985 electrons
__has 58.00% C 1 character in a s0.92 p3 hybrid
__has 42.00% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 0.9925 electrons
__has 59.64% C 1 character in a s0.93 p3 hybrid
__has 40.36% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 0.9970 electrons
__has 58.99% C 1 character in a s0.96 p3 hybrid
__has 41.01% H 5 character in a s orbital

5. A bonding orbital for C2-Cl6 with 0.9957 electrons
__has 45.60% C 2 character in a sp2.97 hybrid
__has 54.40% Cl 6 character in a s0.57 p3 hybrid

6. A bonding orbital for C2-H7 with 0.9945 electrons
__has 62.16% C 2 character in a sp1.94 hybrid
__has 37.84% H 7 character in a s orbital

14. A lone pair orbital for C2 with 0.9726 electrons
__made from a s0.05 p3 hybrid

15. A lone pair orbital for Cl6 with 0.9982 electrons
__made from a sp1.84 hybrid

16. A lone pair orbital for Cl6 with 0.9974 electrons
__made from a sp1.06 hybrid

17. A lone pair orbital for Cl6 with 0.9887 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 Cl 6 Cl 6 Cl 6 Cl 6 Cl 6 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9987 electrons
__has 53.47% C 1 character in a sp2.34 hybrid
__has 46.53% C 2 character in a sp1.54 hybrid

2. A bonding orbital for C1-H3 with 0.9849 electrons
__has 62.33% C 1 character in a s0.93 p3 hybrid
__has 37.67% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 0.9924 electrons
__has 60.31% C 1 character in a s0.90 p3 hybrid
__has 39.69% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 0.9896 electrons
__has 61.67% C 1 character in a s0.92 p3 hybrid
__has 38.33% H 5 character in a s orbital

5. A bonding orbital for C2-Cl6 with 0.9970 electrons
__has 39.75% C 2 character in a sp2.78 hybrid
__has 60.25% Cl 6 character in a s0.69 p3 hybrid

6. A bonding orbital for C2-H7 with 0.9960 electrons
__has 56.31% C 2 character in a sp1.92 hybrid
__has 43.69% H 7 character in a s orbital

15. A lone pair orbital for Cl6 with 0.9979 electrons
__made from a sp0.23 hybrid

16. A lone pair orbital for Cl6 with 0.9878 electrons
__made from a p3 hybrid

17. A lone pair orbital for Cl6 with 0.9440 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 Cl 6 Cl 6 Cl 6 Cl 6 Cl 6 -

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, 2, for C1-H3 with the lone pair acceptor orbital, 14, for C2 is 24.9 kJ/mol.

The interaction of the third lone pair donor orbital, 17, for Cl6 with the lone pair acceptor orbital, 14, for C2 is 101. 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. Only the spin up electron orbital energies are given.

21 ----- 3.078

20 ----- 2.237

19 ----- 1.638


18 ----- -0.156


17 -^--- -4.404


16 -^-v- -7.516

15 -^-v- -8.485

14 -^-v- -9.362


13 -^-v- -10.57

12 -^-v- -10.73

11 -^-v- -11.68


10 -^-v- -14.74


9 -^-v- -18.43


8 -^-v- -21.72


7 -^-v- -190.3
6 -^-v- -190.4

5 -^-v- -190.7


4 -^-v- -248.8


3 -^-v- -266.6


2 -^-v- -268.1


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 = -538.8301333472 Hartrees

Top of page.

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