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Sharma CVK , Panneerselvam K , Shimoni L , Katz H , Carrell HL , Desiraju GR
3-(3',5'-Dinitrophenyl)-4-(2',5'-Dimethoxyphenyl)Cyclobutane- 1,2-Dicarboxylic Acid - Engineered Topochemical Synthesis and Molecular and Supramolecular Properties
Chemistry of Materials. 1994 Aug;6(8) :1282-1292
PMID: ISI:A1994PC72100027   
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The title compound (1b), synthesized using the principles of crystal engineering, exhibits interesting molecular and supramolecular properties. Diacid 1b crystallizes in the triclinic space group P1BAR, a = 8.150(1), b = 8.927(2), c = 17.894(4) angstrom; alpha = 98.91(1), beta = 97.60(1), gamma = 110.62(2)-degrees, and the structure was solved and refined to an R factor of 0.063 on 2910 nonzero reflections. Intramolecular charge transfer in 1b was studied spectroscopically. Through-bond coupling (TBC) and the resultant C-C bond elongation are observed in lb to a moderate extent. A more general Cambridge Structural Database (CSD) study on 1,2-diphenylethanes provides clear evidence for the molecular attributes required for TBC. Diacid 1b forms a host- guest complex with toluene in which the orientation of the guest molecule is perfectly tuned to the steric and electronic requirements of the host. The toluene guest molecule induces a convergent supramolecular cage, while another divergent supermolecule results because of the zigzag hydrogen-bonded chains of carboxyl groups. A water molecule, seemingly inadvertently trapped in the carboxyl channels, is not involved in hydrogen bonding but is a mere space filler. A general analysis of the solvation properties of benzene, toluene, and water is presented.
English Article PC721 CHEM MATER