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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
5-Amino-1-naphthol
Agnieszka Czapik1, Arkadiusz Nitka, Maria Gdaniec
1Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland.
Abstract:
In the title compound, C(10)H(9)NO, the amino and the hydr-oxy groups act both as a single donor and a single acceptor in hydrogen bonding. In the crystal, mol-ecules are connected via chains of inter-molecular ⋯N-H⋯O-H⋯ inter-actions, forming a two-dimensional polymeric structure resembling the hydrogen-bonded mol-ecular assembly found in the crystal structure of naphthalene-1,5-diol. Within this layer, mol-ecules related by a translation along the a axis are arranged into slipped stacks via π-π stacking inter-actions [inter-planar distance = 3.450 (4) Å]. The amino N atom shows sp(3) hybridization and the two attached H atoms are located on the same side of the aromatic ring.
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