STRUCTURES OF CHLORALIDE, D-LACTIC ACID CHLORALIDE, MALIC-ACID CHLORALIDE AND CITRIC-ACID CHLORALIDE

The crystal and molecular structures of chloralide (1), D-lactic acid chloralide (2), malic acid chloralide (3) and citric acid chloralide ( 4) have been determined by X-ray diffraction methods. Compound 1 cryst allizes in the monoclinic space group, P2(1)/c, a = 6.201(2), b = 17.1 1(2), c = 10.357(6) Angstrom, beta = 95.21(4)degrees, Z = 4; compound 2 in the monoclinic space group P2(1), a = 7.600(4), b = 5.902(4), c = 9.743(6) Angstrom, beta = 99.20(5), Z = 2; compound 3 in the monoclin ic space group P2(1)/c, a = 16.500(6), b = 5.819(3), c = 10.120(4) Ang strom, beta = 98.41(3), Z = 4; compound 4 in the monoclinic space grou p P2(1)/c, a = 12.041(3), b = 6.1190(10), c = 17.259(4) Angstrom, beta = 101.85(2), Z = 4. The five-membered ring systems of all the compoun ds are slightly twisted out-of-plane, that of compound 4 being the mos t puckered. The CCl3 group is trans to the second CCl3 group in 1, to the CH3 group in 2 and to the CH(2)COoH group in 3. The two CH2COOH gr oups in 4 are disposed axially with respect to the ring. Dipole moment and Kerr constant data for D-lactic acid chloralide suggest a structu re in solution which is consistent with the X-ray results. The IR spec tra of 2, 3 and 4 are discussed in relation to the structures of these compounds.