NMR spectroscopy in environmental chemistry:1H and13C NMR chemical shift assignments of chlorinated dibenzothiophenes based on two-dimensional NMR techniques andab initio MO and DFT/GIAO calculations

A new potential toxaphene congener: synthesis, GC/EI-MS study, crystal structure, NMR analysis, and ab initio calculations of 3-endo,5-endo-dichloro-7,7-bis-chloromethyl-4-dichloromethyl-tricyclo[2.2.1.02,6]heptane

Abstract A new potential toxaphene congener 3- endo ,5- endo -dichloro-7,7-bis-chloromethyl-4-dichloromethyl-tricyclo[2.2.1.0 2,6 ]heptane 2 has been isolated from reaction mixture obtained by the chlorination of 2- exo ,10,10-trichlorobornane 1 . The X-ray structural analysis of 2 revealed an unusual tricyclic structure, where the two chlorine atoms occupying endo -positions are in close spatial proximity with each other and near to the neighbouring CHCl 2 group. Further, it revealed that the symmetry of the molecule is distorted. The 1 H and 13 C NMR spectra of 2 have been assigned by means of 1 H, 1 H d ouble- q uantum f iltered co rrelation s pectroscop y (DQF COSY), PFG 1 H, 13 C HMQC …