Conformationally-defined phenylethylamines

Evaluation of Some Bicyclic Systems as Conformationally-Defined Phenylethylamines. X-Ray Crystallography. Perhaps the ultimate test of the suitability of a chemical structure for preparing conformationally-defined analogs would be their ability to produce biological effects identical to those of the parent compound. Since this ideal is rarely achieved, and since a "wrong" conformer should be inactive, it is useful to have other criteria with which to evaluate these systems. The bicyclic molecules to be examined in the present study are compounds I-VIII (Figure 7), benzobicyclo[2.2.2]octenes, benzobicyclo [2.2.1]heptenes, and 1,2,3,4-tetrahydro-l,4-epoxynaphthalenes. A number of structural parameters... 

Evaluation of Some Bicyclic Systems as Conformationally-Defined Phenylethylamines. CNDO/2 Calculations on Amphetamines. Quantum mechanical studies on phenylethylamine and amphetamine have been carried out previously by Pullman and coworkers (59,67) using both the semi-empirical PCILO and an ab initio method, and by Hall and coworkers (71 ) using an ab initio method. The results of these two groups were quitesimilar. 

Figure 7. Conformationally defined analogs of phenylethylamines (see text)...

Figure 8. Observed values of n from x-ray crystallography of phenylethylamines showing the agreement with the value of this angle from molecular orbital studies and some conformationally defined analogs (see text)...

Figure 12. Comparison of the distances from the nitrogen to the para-oxygen in some conformationally defined analogs of phenylethylamines with those found from x-ray crystallographic studies reported for phenylethylamines (see text)...

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