We are studying a group of substituted cyclohexenecarboxylic acids whose enantiomers differ only in the placement of the double bond in the cyclohexene ring. Twelve of such molecules were synthesized before and characterized by X-ray single crystal structures. These molecules were analyzed using the bond angles, lengths and other data from X-ray crystallography. The placement of the double bond for each molecule was determined using the bond lengths (Å) and known values for various double and single bonds in a ring. The results of the analysis showed that the lengths were very similar based on the hybridization of the carbons. The single bonds lengths ranged from 1.456-1.509 Å, with the outermost values having only a 3.6% difference. The average of all single bond lengths assigned to the twelve molecules was 1.47 Å, which results in a 4.7% difference from the single bond length known to literature. Double bond lengths ranged from 1.346-1.363 Å and in the same manner had a 1.3% difference. The average double bond length of molecules, 1.36 Å, resulted in a 2.2% different when compared to literature length of double bonds. Furthermore, the dimerization of the carboxylic acids was analyzed using these proven placements of double bonds in the structure. All but one molecule were shown to dimerize in the R-S packing. One discrepant molecule, however, dimerized in the R-R configuration for one dimer and the S-S for the other.

Study of the solid-state enantiomeric interaction of a group of substituted cyclohexenecarboxylic acids using X-ray crystallography

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