engleski

Nitro Derivatives of Glutethimide

Crystallographic experiments performed on single crystals of m-nitroglutethimide, 3-(3'-nitrophenyl)-3-ethylpiperidine-2,6-dione, C~13~H~14~N~2~O~4~, (I), and of o,p-dinitroglutethimide, 3-(2',4'-dinitrophenyl)-3-ethylpiperidine-2,6-dione, C~13~H~13~N~3~O~6~, (II), have unambiguously confirmed their molecular structures. According to the HPLC data it has been found that both title compounds are byproducts in the nitration of glutethimide. The six-membered glutarimide rings of (I) and (II) have an envelope conformation with C4 atom out of plane, i.e. with C4-exo puckering in (I), but with C4-endo puckering in (II). Steric hindrances are, most likely, responsible for the observed conformational dissimilarity. The molecular structure of compound (I), unlike compound (II), is very similar to that of aminoglutethimide. Enantiomeric molecules in both compounds are linked together through pairs of symmetric R~2~^2^(8) intermolecular hydrogen bonds forming centrosymmetric racemic dimers.

glutethimide; nitration; puckering; exo; endo

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