Toxaphene insecticide: Identification and toxicity of a dihydrocamphene component

Landrum, Peter F.; Pollock, Gerald A.; Seiber, James N.; Hope, H.; Swanson, K.L.

doi:10.1016/0045-6535(76)90021-7

Cited by 30 publications

(8 citation statements)

References 6 publications

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“…Finally, a fourth research group identified a compound (11), which does not have the bornane skeleton, and they also identified again compound (5) (Landrum et al, 1975). The non-bornanoid structure of compound (11) was confirmed by X-ray structural analysis (Landrum et al, 1976).…”

Section: B) F~e~~!~!~~-~f_i~~~e~~~~mentioning

confidence: 75%

“…In analyzing the 1 H-NMR spectrum, the assumption was made that both components of Taxicant A are octachlorobornanes. The following table (II) gives a chemical shift data for these compounds (Matsumura et .al., 1975}. The first toxaphene component known to retain the ring structure of camphene 2,5,6-exo,8,8, 9,10-heptachlorodihydrocamphene (11) was determined by single crystal X-ray diffraction method and 1 H-NMR spectroscopy (Landrum et al, 1976 [11]…”

Section: Spectroscopical Studies Of High-chlorinated Bornane Derivativesmentioning

confidence: 99%

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Toxaphene (Camphethlor). A Special Report

1979

Pure and Applied Chemistry

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Section: B) F~e~~!~!~~-~f_i~~~e~~~~mentioning

confidence: 75%

Section: Spectroscopical Studies Of High-chlorinated Bornane Derivativesmentioning

confidence: 99%

Toxaphene (Camphethlor). A Special Report

1979

Pure and Applied Chemistry

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“…5 The formation of polychlorinated dihydrocamphenes is not as easy to understand as it would seem. Landrum et al 7 postulated addition of HCl to the double bond of camphene. According to Krock et al 5 this is very unlikely since an ionic attack at the double bond is more favourable due to the stabilization effect of the Wagner-Meerwein rearrangement resulting in the formation of bornane.…”

Section: Formation Of Polychlorinated Dihydrocamphenesmentioning

confidence: 99%

“…This is indeed the case for all dihydrocamphenes described in this article and reported previously. 6,7,9 Crystal structure of 3-exo,5-exo,6-exo,9,10,10-hexachlorodihydrocamphene (2). The crystal structure of the hexachlorodihydrocxamphene 2 has been determined by single The density of the compound calculated from these values and from the molar mass of 344.90 g is 1.707 g cm -3 .…”

Section: Formation Of Polychlorinated Dihydrocamphenesmentioning

confidence: 99%

“…Actually, these mass spectra must probably be attributed to camphenes, because new insights in synthetic pathways of technical toxaphene indicate the formation of camphenes and dihydrocamphenes. 5 Previously, Landrum et al6,7 reported the identification of a heptachlorodihydrocamphene in technical toxaphene and Hainzl et al 8 reported the isolation of five polychlorocamphenes from a toxaphene standard. In addition, Tribulovich et al 9 showed that cis-and trans-5-exo,10-…”

Section: Introductionmentioning

confidence: 99%

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Syntheses, structures and spectroscopy of polychlorinated dihydrocamphenes. An experimental and theoretical study

Koivisto¹,

Kolehmainen²,

Nikiforov³

et al. 2002

Arkivoc

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Nine novel polychlorinated dihydrocamphenes (1-9) have been isolated from reaction mixtures obtained by the chlorination of lower chlorinated monoterpenes. These compounds are potential congeners of insecticide toxaphene. The H NMR spectral analysis. In the case of 2, the structure has been determined by X-ray methods. Full geometry optimizations have been performed at the ab initio HF/6-31G* level for a comparison with the conformational and structural properties obtained from the NMR-and X-ray experiments. The optimized geometries are in excellent agreement with the experimental structures. In addition, rotation barriers of compounds 7 and 9 have been characterized with the semiempirical AM1 method. The gauge-including atomic orbital (GIAO) method have been employed to calculate 13 C chemical shifts of 1-9 using density functional theory (DFT) at the B3LYP/6-311G* level and the HF/6-31G* optimized structures as geometry input. A comparison of the calculated and experimental data yielded a regression equation, which with added indicator variable (the number of chlorine atoms attached to each carbon) is capable of the accurate prediction of carbon chemical shifts for these compounds.

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Selective sensitivity of highly chlorinated species in negative ion mass spectrometry: Implications for complex mixture analysis

Erhardt-Zabik

Watson

Zabik

1990

Biol. Mass Spectrom.

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In attempts to quantify complex chlorinated hydrocarbon mixtures by negative ion mass spectrometry (MIMS), a selective sensitivity was observed which was not observed using the technique of electron capture detection (ECD) with conventional gas-liquid chromatography. The phenomenon was systematically studied using chlorinated phenols, chlorinated biphenyl isomers and a mixture of chlorinated bicyclic species. Results indicated that for two aromatic series there is an increase in molar response to both ECD and NI/MS with increased degree of c h l 0 r i~-tion. However, overall an increase in molar response was observed for a series of aliphatic bicyclic compounds only when analyzed by NIIMS; i.e. the ECD molar response did not vary with increasing chlorination of the bicyclic system. A procedure for optimizing mass spectrometer parameters has been developed for quantifying complex chlorinated hydrocarbon mixtures. A simple mixture which mimics the halogenation in a complex mixture is used to determine the response of the instrument to various degrees of chlorination. The recommended calibration procedure optimizes instrumental parameters such as moderating gas pressure, filament current and electron energy so that complex chlorinated mixtures such as those found in toxaphene residues can be reliably quantified.

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Toxaphene insecticide: Identification and toxicity of a dihydrocamphene component

Cited by 30 publications

References 6 publications

Toxaphene (Camphethlor). A Special Report

Toxaphene (Camphethlor). A Special Report

Syntheses, structures and spectroscopy of polychlorinated dihydrocamphenes. An experimental and theoretical study

Selective sensitivity of highly chlorinated species in negative ion mass spectrometry: Implications for complex mixture analysis

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