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Updated: Jun 5, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
N-(4-Amino-phen-yl)-1,8-naphthalimide hemihydrate
Fang-Fang Jian1, Li-Ming Wang, Li Du
1New Materials and Functional Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China.
Abstract:
The title compound, C(18)H(12)N(2)O(2)·0.5H(2)O, was prepared by the reaction of 1,4-phenyl-enediamine with 1,8-naphthalic anhydride in refluxing dimethyl-formamide. The structure is stabilized by N-H⋯O and O-H⋯O hydrogen bonds. There are π-π stacking inter-actions [centroid-centroid distances of 3.718 (2), 3.510 (2) and 3.546 (2) Å] and C-H⋯π inter-actions between the mol-ecules. The water molecule lies on a twofold rotation axis. Its two H atoms are disordered equally over two positions.
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