Health & Environmental Research Online (HERO)


Print Feedback Export to File
1989983 
Journal Article 
DDT: Participation in untraviolet-detectable, charge-transfer complexation 
Wilson WE, , JR; Fishbein L, , JR; Clements ST, , JR 
1971 
1 
Science
ISSN: 0036-8075
EISSN: 1095-9203 
HAPAB/71/01069 
171 
REF:19 
HAPAB The charge-transfer interaction of the chlorophenyl groups of o,p'- and p,p'-DDT, -DDD, -DDMS and -DDA and bis(p-chlorophenyl)-methane alone and with TCNE (tetracyanoethylene) were studied using UV (ultraviolet) spectroscopy. Solutions of 0.00001, 0.00002 and 0.00003 M DDT were prepared in 10, 20 and 30% 2-propanol in water, respectively. UV spectra of DDT in hexane, isoamyl alcohol, isobutanol, 2-propanol or 30% 2-propanol were qualitatively similar (absorption maxima at 220 and 237 nm, with a shoulder at 237 nm). A solution of 0.00002 M DDT in 20% 2-propanol gave a single absorption maximum at 240 nm. The UV absorbance changes were assumed to be evidence of selfassociation of DDT and that the bathochromic shifts observed in the UV spectrum represented intermolecular charge-transfer complexation of DDT with DDT. The spectrum obtained from 0.00001 M DDT in 10% 2-propanol in water with pure 2-propanol as a reference was qualitatively the same as that reported to represent a charge-transfer complex involving DDT and some unknown component of cockroach nerve cord (Matsumura and O'Brien, 1966). TCNE formed yellow complexes with chlorobenzene, benzene and toluene and the charge-transfer band was most intense with toluene (402 nm). The weaker TCNE-benzene and -chlorobenzene bands occurred at about 380 nm. TCNE also formed yellow complexes with DDT and the DDT metabolites used in this study. The charge-transfer bands for TCNE-DDT, -DDD and -DDMS were essentially the same; they simulated that for chlorobenzene, but absorbance values were much lower than would be expected from These data give evidence that, although the chlorophenyl groups of DDT, DDD or DDMS are weaker electron donors than chlorobenzene, the p-chlorophenyl groups of DDT can participate in charge-transfer interaction with TCNE. 1971