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The molecular geometry of 2, 2'-chloro biphenyl was calculated using two
semi-empirical methods (AM1 and PM3) as well as the ab initio HF-SCF
method with three different basis sets (6-21G, 6-31G, and DZV).
Table 1: Dipoles, dihedral angles, and energies for each level of theory.
2,2'-chlorobiphenyl
| Dipole (Debye)
| Dihedral Angle (°)
| Engergy (Hartree)
|
AM1
| 1.526426
| 90.3
| -87.9499
|
PM3
| 1.052166
| 85.0
| -80.0244
|
6-21G
| 2.468097
| 85.0
| -1377.4957
|
6-31G
| 3.139907
| 84.8
| -1377.8424
|
DZV
| 2.962393
| 92.2
| -1377.8
|
Literature
| -------
| 84.9(3)
| -------
|
Besides reference (3), data concerning bond lengths and bond angles
could not be found for this molecule. A close comparison molecule was
chlorobenzene, and data for the corresponding bond lengths and angles
for literature comparison can be found using this link:
https://cccbdb.nist.gov/exp2.asp (2). The following buttons show the calculated geometries for each level of theory.
Molecular orbitals were also calculated in the geometry optimization. The HOMO was determined by filling
orbitals starting with the lowest energy orbital and selecting the
highest energy occupied orbital. The LUMO was determined by taking the
lowest energy orbital that was not occupied by electrons.
For comparison vibrational frequencies, no data could be found for this
molecule. For a comparison IR spectrum, here is a link to a spectrum for
chlorobenzene, which would have similar stretches
http://webbook.nist.gov/cgi/cbook.cgi?ID=C108907&Units=CAL&Type=IR-SPEC.
Here are some example vibrations from this 2, 2'-chlorobiphenyl
Similar to the vibrational frequencies, no electronic transition data
could be found for comparison to the calculations made. The following
link shows a UV-Vis spectrum for a similar molecule, chlorobenzene.
http://webbook.nist.gov/cgi/cbook.cgi?ID=C108907&Units=CAL&Mask=400#UV-Vis-Spec.
Table 2: UV-Vis absorption energy for ab initio methods
|
UV-Vis Absorption (cm-1)
|
6-21G
|
52909.92
|
6-31G
|
51858.32
|
DZV
|
50692.79
|
Based on template by A. Herráez as modified by J. Gutow
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