Carbon‐13 NMR spectra of some chlorinated polycyclodiene pesticides

Abstract

~~Carbon-13 NMR spectra have been obtained for aldrin, dieldrin, isodrin, endrin, heptachlor, heptachlor oxide and 24 of theii degradationlconversion products. Chemical shifts were assigned on the basis of (1) comparison among the spectra, (2) single frequency, off-resonance decoupling experiments, (3) substituent effects derived for norbornanes and (4) spectra obtained with an added lanthanide shat reagent. The substituent effects previously reported for norbornanes were found to be applicable for establishing trends in the chemical shifts for many of the compounds studied.

NMR spectroscopy in environmental chemistry:1H and13C NMR parameters of tricyclic polychlorinated C10 hydrocarbons and their oxy derivatives based on two-dimensional NMR techniques

“…An HMBC connectivity between H-3a and C-5 gives the final verification for the correct assignment for C-5 and C-6 of 2. This assignment is also in agreement with that given by ApSimon et al 5 On the other hand, the 1 H and 13 C NMR chemical shift assignments for 3, 4 and 5 reported previously 6 have several deviations in comparison with our present results. Further, as far as we know, the n J(H,H) data for 3 have not been reported previously.…”

Cellular Localization of Dieldrin and Structure–Activity Relationship of Dieldrin Analogues in Dopaminergic Cells

“…1 Desmethylene Dieldrin (1,8,9,10,11,11-Hexachloro-4,5epoxy-2,3-7,6-endotricyclo[6.2.1.0 2,7 ]undec-9-ene). Using methods adapted from literature methods, 14,19,21,22 we added 3chloroperbenzoic acid (mCPBA) (0.08 g, 0.5 mmol) in 2.0 mL of dichloromethane dropwise to desmethylene aldrin (0.1 g, 0.3 mmol) in 2.0 mL of dichloromethane and stirred at room temperature for 2 h. The reaction mixture was extracted twice with water. The organic layer was then dried with magnesium sulfate and the product purified by column chromatography on silica gel with a mobile phase of 4:1 hexanes to acetone, resulting in a 50% yield.…”

“…Using methods adapted from literature methods, ,− we placed hexachlorocyclopentadiene (1.0 g, 0.004 mol, 0.6 mL) and 1,4-cyclohexadiene (1.3 g, 0.016 mol, 1.51 mL) under argon and stirred them at 110 °C for 44 h. The product was purified by column chromatography on silica gel with hexanes as mobile phase, resulting in a 25% yield. 1 H NMR (CDCl 3 ): δ 1.90–1.99 and 2.35–2.44 (m, 4H, CH 2 ), 2.98–3.09 (m, 2H, CH), 5.86 (m, 2H, HCCH).…”

Mechanisms of Toxicity and the Structure-Activity Relationships of Molinate and Dieldrin

“…1 H NMR (CDCl 3 ): δ 1.90--1.99 and 2.35--2.44 (m, 4H, CH 2 ), 2.98--3.09 (m, 2H, CH), 5.86 (m, 2H, HC=CH); 13 C NMR (CDCl 3 ): δ 21.9, 45.8, 82.5, 103.2, 126.7, 131.6; MS (EI) m/z calcd for C 11 H 8 Cl 6 349.9, found m/z 349.9. Desmethylene Dieldrin (1,8,9,10,11,11--hexachloro--4,5-epoxy--2,3--7,6--endo--tricyclo[6.2.1.0 2,7 ]undec--9--ene)Adapted from literature methods(202,208,210,211), 3--chloroperbenzoic acid (mCPBA) (0.08 g, 0.5 mmol) in 2 mL of dichloromethane was added dropwise to a desmethylene aldrin (0.1 g, 0.3 mmol) in 2 mL dichloromethane, and stirred at RT for 2 h. Reaction mixture was extracted twice with water. The organic layer was then dried with magnesium sulfate and the product purified by column chromatography on silica gel with a mobile phase of 4:1 hexanes to acetone, resulting in a 50% yield.…”