Related Experiment Video
Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1,8-Bis(4-amino-benzo-yl)-2,7-dimeth-oxy-naphthalene
Takahiro Nishijima1, Kotaro Kataoka, 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 {systematic name: [8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C(26)H(22)O(4)N(2), possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis. In the crystal, the mol-ecules inter-act through inter-molecular N-H⋯O hydrogen bonds between the amino and meth-oxy groups on the naphthalene ring systems and N-H⋯π inter-actions between the amino groups and the naphthalene rings. Furthermore, weak C-H⋯O hydrogen bonds and π-π stacking inter-actions between the benzene rings are observed. The centroid-centroid and inter-planar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent mol-ecules are 3.6954 (8) and 3.2375 (5) Å, respectively. The dihedral angle between the mean planes of the benzene ring and the naphthalene ring system is 83.59 (5)°. The benzene ring and the carbonyl group in the benzoyl unit are almost coplanar [C-C-C-O torsion angle = 175.91 (10)°].
Related Concept Videos
Nomenclature of Aromatic Compounds with a Single Substituent
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
NMR Spectroscopy of Aromatic Compounds
Nomenclature of Aryl and Heterocyclic Amines
Electrophilic Aromatic Substitution: Nitration of Benzene
2° Amines to N-Nitrosamines: Reaction with NaNO2

