Mass spectrometric studies of the toxaphene components 2-exo,3-endo,5-exo,6-endo,8,8,10,10-octachlorobornane (T2) and 2-exo,3-endo,5-exo,6-endo,8,8,9,10,10-nonachlorobornane (T12).
The electron capture negative ion mass spectra of the title compounds show prominent [M-Cl]- ions, and low-abundance ions formed by further elimination of HCl or Cl2. The electron ionization positive ion mass spectra are complex, but structurally informative fragmentations are observed. In particular, fragmentations involving elimination of C2H2Cl2, and not of C2H4, C2H3Cl, C2HCl3 or C2Cl4, indicate that two chlorines are bound to the C2-C3 and C5-C6 units of a norbornane skeleton. Furthermore, from M+., elimination of HCl is enhanced with respect to Cl., relative to toxicants A and B, which are major components of commercial toxaphene; this result suggests that one chlorine atom is bound to each of carbons 2, 3, 5 and 6. Both compounds have CHCl2 substituents. Several of the fragmentation pathways appear to terminate at ions that may be tropylium analogues.
Stern
G A
GA
Department of Fisheries and Oceans, Freshwater Institute, Winnipeg, Canada.
Muir
D C
DC
Westmore
J B
JB
Buchannon
W D
WD
D000273:Adipose Tissue / Q000737:chemistry; D000818:Animals; D001892:Camphanes / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D006843:Hydrocarbons, Chlorinated / Q000032:analysis*; D013058:Mass Spectrometry; D014112:Toxaphene / Q000032:analysis*; D014907:Whales
D001892:Camphanes; D006843:Hydrocarbons, Chlorinated; C079680:2,3,5,6,8,8,10,10-octachlorobornane; C079681:2,3,5,6,8,8,9,10,10-nonachlorobornane; D014112:Toxaphene