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Title: (E)-2-(2-Pyridinyl)-3-(2-pyridinylmethylene)chromanone, a 1:2 condensation product of 2′-hydroxyacetophenone and pyridine-2-aldehyde, showing some interesting properties
Authors: Mondal, Rina
Sepay, Nayim
Mallik, Asok K
Keywords: Chromanone;2′-hydroxyacetophenone;Pyridine-2-aldehyde;2-pyridinylmethylene;Endocyclic isomer;X-ray;DFT
Issue Date: Jul-2019
Publisher: NISCAIR-CSIR, India
Abstract: An efficient synthesis of (E)-2-(2-pyridinyl)-3-(2-pyridinylmethylene)chromanone has been done by treatment of 2′-hydroxyacetophenone and pyridine-2-aldehyde in aqueous methanolic KOH. The compound has been obtained as crystalline precipitate from the reaction medium, which was suitable for spectral analysis and X-ray crystallographic study. It possesses an interesting intramolecular hydrogen bonding between the C2-H and the nitrogen of 2-pyridinylmethylene moiety. At room temperature, it is stable for months in the crystalline state, but in CDCl3 solution it gradually changes to the endocyclic isomer 2-(2-pyridinyl)-3-(2-pyridinylmethyl)chromone. From analysis of the X-ray crystallographic data and DFT studies, possible explanations have been given for the stability of the compound in the crystalline state and its isomerization in solution.
Page(s): 805-810
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.58B(07) [July 2019]

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