What are the symmetry elements of the isomers of dichlorocyclobutane?
1 Answer
Since you have not specified which isomers, I will simply list four of them (assuming they are on different carbons):
From left to right, we have the cis-1,3, trans-1,3, trans-1,2, and cis-1,2 isomers. I will label them from left to right, isomers (1), (2), (3), and (4).
(1):
(2):
(3):
(4):
So basically:
(1): Identity, one rotation axis, two reflection planes
(2): Identity, one rotation axis, one point of inversion, one reflection plane
(3): Identity, one rotation axis
(4): Identity, one reflection plane
DISCLAIMER: Long answer! Possibly difficult to visualize...
The possible, primary symmetry elements overall (for any compound) are:
E , the identity element, for completeness's sake.C_n , the principal rotation axis, where a rotation of360^@/n about this axis returns the original molecule. This is defined to require the largest rotation angle to return the original molecule.
We define this to be along thebb(z) axis.C_n' , any other rotation axis, defined similarly; just something that isn't the previously-definedC_n . It could be perpendicular.sigma_v , the vertical reflection plane, colinear with the principal rotation axisC_n . Generally, crosses through atoms.sigma_h , the horizontal reflection plane, generally on the plane of a cyclic molecule that is perpendicular to theC_n axis.
If noC_n axis exists except for the trivialC_1 (C_1 = E ), then we assign a reflection plane assigma_h .sigma_d , the dihedral reflection plane, generally in between two atoms, bisecting a bond (this is not common unlesssigma_v andsigma_h are also identified).i , the point of inversion. Basically you take the coordinates(x,y,z) and swap them with the coordinates(-x,-y,-z) .
Obviously, all four isomers have
ISOMER (1)
- There is one
C_n axis through the ring, through the plane of the screen. That is abb(C_2) principal rotation axis, along thez -axis. Therefore, the plane of the ring is thexy -plane. - There is one
bb(sigma_v(xz)) vertical reflection plane bisecting the molecule through carbon-1 and carbon-3 (perpendicular to the ring). - There is one more
bb(sigma_v(yz)) vertical reflection plane bisecting the molecule through carbon-2 and carbon-4 (perpendicular to the ring).
That, by the way, assigns this molecule to a
ISOMER (2)
Compared to (1), there is no longer a
- There is one
bb(C_2) axis bisecting the molecule through carbon-2 and carbon-4. We now define that as itsz -axis. Let the plane of the molecule be theyz -plane, then (so that thex axis is through the plane of the screen). - There is one point of inversion,
bb(i) . Try taking carbon-1 and carbon-3, and switching their coordinates. Your chlorines would exactly swap places. - There is one
bb(sigma_h(xz)) vertical reflection plane bisecting the molecule through carbon-1 and carbon-3 (perpendicular to the ring). Since it is perpendicular toC_2 , it is still considered "horizontal". We've just reoriented our axes.
That, by the way, assigns this molecule to a
ISOMER (3)
Compared to (2), there is no point of inversion
Using the same reasoning as in (1) and (2):
- There is a
bb(C_2) principal rotation axis bisecting theC_1-C_2 bond, and we define that as thez -axis sincen is as low as possible (C_1 = E ).
And I think that's it... I cannot find any reflection planes. There is no point of inversion as I mentioned before, since the chlorines are both on the same side.
So this is, by the way, assigned to a
ISOMER (4)
Compared to (3), there is actually a reflection plane, but no
- All I see is a
bb(sigma_h) reflection plane, since there is noC_n axis I can find. This is bisecting the molecule through theC_1-C_2 bond (perpendicular to the plane of the screen).
So this is, by the way, assigned to the
Does this make sense? It may require you to pull out a model kit to visualize this.