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Updated: May 26, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
N,N'-Bis(pyridin-2-yl)benzene-1,4-diamine-naphthalene (2/1)
Barbara Wicher1, Maria Gdaniec
1Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland.
Abstract:
The asymmetric unit of the title compound, C(10)H(8)·2C(16)H(14)N(4), consists of one mol-ecule of N,N'-bis-(pyridin-2-yl)benzene-1,4-diamine (PDAB) and one half of the centrosymmetric naphthalene mol-ecule. The PDAB mol-ecule adopts a non-planar conformation with an E configuration at the two partially double exo C N bonds of the 2-pyridyl-amine units. In the crystal, N-H⋯N hydrogen bonds between the PDAB mol-ecules generate a cyclic R(2) (2)(8) motif, leading to the formation of PDAB tapes extending along [100]. The tapes are arranged into (010) layers and the naphthalene mol-ecules are enclosed in cavities formed between the PDAB layers.
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