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(E)-2-(2-Pyridinyl)-3-(2-pyridinylmethylene)chromanone, a 1:2 condensation product of 2′-hydroxyacetophenone and pyridine-2-aldehyde, showing some interesting properties

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Field	Value

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

Creator	Mondal, Rina Sepay, Nayim Mallik, Asok K

Subject	Chromanone 2′-hydroxyacetophenone Pyridine-2-aldehyde 2-pyridinylmethylene Endocyclic isomer X-ray DFT

Description	805-810 An efficient synthesis of (<em>E</em>)-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 C<sub>2</sub>-H and the nitrogen of 2-pyridinylmethylene moiety. At room temperature, it is stable for months in the crystalline state, but in CDCl<sub>3</sub> 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.

Date	2019-07-11T05:38:07Z 2019-07-11T05:38:07Z 2019-07

Type	Article

Identifier	0975-0983(Online); 0376-4699(Print) http://nopr.niscair.res.in/handle/123456789/49110

Language	en_US

Rights	<img src='http://nopr.niscair.res.in/image/cc-license-sml.png'> <a href='http://creativecommons.org/licenses/by-nc-nd/2.5/in' target='_blank'>CC Attribution-Noncommercial-No Derivative Works 2.5 India</a>

Publisher	NISCAIR-CSIR, India

Source	IJC-B Vol.58B(07) [July 2019]