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Com o objetivo de realizar uma analise comparativa do efeito de compressao anelar e do Cl no deslocamento quimico dos carbonos clorados tencionados, foram analisados os deslocamentos quimicos de 27 estruturas policiclicas cloradas e nao cloradas derivadas dos inseticidas “aldrin” (5) e “isodrin” (14). Os compostos foram divididos em quatro grupos de acordo com a conformacao e numero de aneis: tetraciclododecanos endo-exo, tetraciclododecanos endo-endo, pentaciclododecanos e hexaciclododecanos. A comparacao do deslocamento quimico de carbono-13 entre compostos clorados e nao-clorados mostrou que, quando C-9 e C-10 sao carbonos olefinicos, ocorre um deslocamento para baixa frequecia de 0.5-2.4 ppm para os tetraciclododecanos endo-endo e de 4.7-7.6 ppm para os tetraciclododecanos endo-exo. Para C-11, a variacao do deslocamento quimico atinge valores de 49-53 ppm para os tetraciclicos endo-exo e endo-endo, de 54 ppm para o pentaciclico e de 56-59 ppm para os hexaciclicos. A partir desses dados foi possivel observar a influencia da compressao anelar no deslocamento quimico. In order to establish a comparative analysis of chemical shifts caused by ring compression effects or by the presence of a chlorine atom on strained chlorinated carbons, a series of the chlorinated and dechlorinated polycyclic structures derived from “aldrin” (5) and “isodrin” (14) was studied. Compounds were classified in four different groups, according to their conformation and number of ring such as: endo-exo and endo-endo tetracyclics, pentacyclics and hexacyclics. The 13 C chemical shift comparison between the chlorinated and dechlorinated compounds showed that when C-9 and C-10 are olefinic carbons, it occurs a shielding of 0.5-2.4 ppm for endo-endo tetracyclics and of 4.7-7.6 ppm for endo-exo tetracyclic. The chemical shift variation for C-11 reaches 49-53 ppm for endo-exo and endo-endo tetracyclics, 54 ppm for pentacyclic and 56-59 ppm for hexacyclic compounds. From these data, it was possible to observe the influence of ring compression on the chemical shifts.

Skeletal and chlorine effects on 13C-NMR chemical shifts of chlorinated polycyclic systems