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Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
(2,7-Dimeth-oxy-naphthalen-1-yl)(3-nitro-phen-yl)methanone
Kotaro Kataoka1, Takahiro Nishijima, Atsushi Nagasawa
1Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan.
Abstract:
The title compound, C(19)H(15)NO(5), has an intra-molecular C-H⋯O=C hydrogen bond between a naphthalene H atom and the O atom of the carbonyl group. The inter-planar angle between the naphthalene ring system and the benzene ring is 69.59 (5)°. The dihedral angle between the bridging carbonyl C-C(=O)-C plane and the naphthalene ring system is 61.02 (6)°, which is far larger than that between the bridging carbonyl plane and the benzene ring [12.68 (7)°]. The nitro group is slightly out of the plane of the benzene ring [O-N-C-C torsion angle = 4.97 (17)°]. In the crystal, the packing is mainly stabilized by C-H⋯O inter-actions between an H atom of the benzene ring and an O atom of the nitro group.
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As with other organic compounds, alcohols and phenols...
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The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H