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These trends can be attributed to the fact that the dipoles of the substituents in a cis isomer will add up to give an overall molecular dipole. In a trans isomer, the dipoles of the substituents will cancel out [7] due to being on opposite sides of the molecule. Trans isomers also tend to have lower densities than their cis counterparts ...
Industrially both isomers arise as byproducts of the production of vinyl chloride, which is produced on a vast scale. Unlike 1,1-dichloroethylene, the 1,2-dichloroethylene isomers do not polymerize. [1] trans-1,2-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications. [5]
In the cis isomer the two polar C−Cl bonds are on the same side of the C=C double bond and the molecular dipole moment is 1.90 D. In the trans isomer, the dipole moment is zero because the two C−Cl bonds are on opposite sides of the C=C and cancel (and the two bond moments for the much less polar C−H bonds also cancel).
The trans isomer is more stable by approximately 50 kJ/mol, and the barrier to isomerization in the ground state is approximately 100 kJ/mol. Azobenzene photoisomerization. The trans form (left) can be converted to the cis form (right) using a UV wavelength of 300–400 nm. Visible illumination at >400 nm converts the molecule back to the trans ...
The transition dipole moment is useful for determining if transitions are allowed under the electric dipole interaction. For example, the transition from a bonding π {\displaystyle \pi } orbital to an antibonding π ∗ {\displaystyle \pi ^{*}} orbital is allowed because the integral defining the transition dipole moment is nonzero.
The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]
The cis isomer has C 2v symmetry and the trans isomer has C 2h symmetry. These isomers can interconvert, but the process is slow enough at low temperature that the two can separated by low-temperature fractionation. [clarification needed] The trans isomer is less thermodynamically stable [2] but can be stored in glass vessels
Most o-xylene is produced by cracking petroleum, which affords a distribution of aromatic compounds, including xylene isomers. m -Xylene is isomerized to o -xylene. Net production was approximately 500,000 tons in the year 2000.