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In this study, several N-(p-substituted-arylsulfonyl)phthalimides (1a-e) were synthesized. The synthesized compounds were then examined with respect to their substitution reactions with t-butylamine, diethylamine, cyclohexylamine, and trans-1,2-diaminocyclohexane in acetonitrile. In order to determine the mechanism, substituent effect, activation entropy, and nucleophile effect were used as criteria

The title compound, C12H9N3O4S, synthesized by condensation of 5-nitrothiophene-2-carbaldehyde and 2-methyl-3-nitroaniline, crystallizes in the orthorhombic space group P212121. In the molecule, the aromatic benzene and thiophene rings are twisted with respect to each other, making a dihedral angle of 23.16 (7)°. In the crystal, molecules are linked by intermolecular C—H...O hydrogen bonds into chains extending along the c-axis direction. Weak π–π stacking interactions along the a-axis direction provide additional stabilization of the crystal structure. The roles of the various intermolecular interactions were clarified by Hirshfeld surface analysis, which reveals that the crystal packing is dominated by O...H (39%) and H...H (21.3%) contacts. The crystal studied was refined as a two-component inversion twin.

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In the title compound, C 26 H 19 NO 3 , the phenyl rings form a dihedral angle of 46.8 (1)° and they make dihedral angles of 79.6 (1) and 67.7 (1)° with the naphthalene ring. The hydroxy groups involve in O-H···O intramolecular H-bonds. CommentNaphthylamine moiety is found to be extremely carcinogenic (Sigma Chemical Company, 1994). Naphthylamine is employed as a disinfectant or insecticide (moth balls) and for the preparation of hydronaphthalenes, phthalic acid and anthronilic acid, but mainly for the manufacture of great many derivatives, which are employed in the colour industry (Tedder & Nechvatal, 1967;Kipping & Kipping, 1961). C 26 H 19 NO 3 existence to tautomerizes in liquid phase (Tezcan, 1990). The intramolecular distance in this structure [H3O···O1 2.416 (4) Å], indicates the presence of hydrogen bonding which occur in the tautomeric enol form. The similar structure dibenzoylacetic acid-N-carboxymethylamide (Fabian et al., 1992) is keto form. The crystal structure determination of the title compound was undertaken in order to elucidate the molecular conformation and hydrogen bonding. The structure has the enolic form in solid phase.The bond lengths and angles in this structure are normal and comparable to those observed in dibenzoylacetic acid-Ncarboxymethylamine (Fabian et al., 1992) and 3-endo-(1-naphthylamino)camphor (Yagi, Ohashi, Ishige & Maeda, 1989).The naphthalene ring is planar with a maximum deviation of 0.040 (4) Å for C6. The phenyl ring planes form a dihedral angle of 46.8 (1)° between them. The naphthalene ring make dihedral angles of 79.6 (1)° and 67.7 (1)°, respectively with the two phenyl rings. The hydroxy group involve in O-H···O intramolecular hydrogen bond with the carbonyl oxygen. The detail of the hydrogen bond is O3-H3O 1.11 (5), O3···O1 2.416 (4), H3O···O1 1.35 (5)Å and O3-H3O···O1 157 (5)°. ExperimentalTo a solution of dibenzoyl-L-acetic acid-N-carboxymethyamide (0.325 g m) was added 1-naphthylamine (0.150 g m) and toluene (25 ml). The mixture was boiled under reflux for 3 h.(C=O), δ=172.32-105.95 p.p.m. (olefenic carbon). RefinementThe temperature of the crystal was maintained at 173 (2) K by using the Watlow control systems. The data collection was covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0,