Comparison of the conformation in the crystal and in solution of 1-(nitromethyl)-3-phenylphthalan

Abstract

In connection with the stereochemical problem posed by 1, 3-disubstituted phthalans, we have determined the crystal structure of trans-1-(nitromethyl)-3_phenylphthalan, I (2). In the crystal, the dihedral angle between the C-H_X and the C-NO_2 bonds is found to be 90" with the nitro group oriented away from the phthalan part of the molecule. It is of special interest to determine whether the same conformation is also favored in solution and to this end we have analyzed the proton magnetic resonance spectra of I in CDCl_3.

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