Table 3. Comparing properties of isomers 2, 22, and 23via DFT calculations ^a .

Subs.	d(C–I)	d(I–F)	q C	q I	q F	θ C–I–F	θ F–I–F	φ C–C–I–F b
o-CF3	2.13 Å	2.01 Å c	–0.248	1.419	–0.627 d	86° e	172°	40° f
m-CF3	2.13 Å	2.02 Å g	–0.251	1.409	–0.628	87°	174°	0°
p-CF3	2.13 Å	2.03 Å h	–0.300	1.502	–0.649	87°	175°	0°

^aCalculations peformed at wB97xD/cc-pvdz, with a cc-pvdz-PP basis set used for the iodine atom. C refers to ipso carbon atom and F refers to fluorine atom bound to iodine, unless otherwise specified.

^bDihedral angle of C_ortho–C_ipso–I–F.

^cAverage between 2.00 and 2.02 (not equal bond lengths).

^dAverage between –0.621 and –0.633.

^eAverage between 85° and 87°.

^fF atom proximal to substituent (dihedral angle is 38° for distal F).

^gStructure is nearly symmetric about F–I–F (mirror plane).

^hStructure is symmetric about F–I–F (mirror plane).