Crystal Structure of 2-(Ethoxymethylene)malononitrile and DFT Evaluation of the C-H···N≡C Close Contacts Energy

2-(Ethoxymethylene)malononitrile (<b>1)</b> is a very convenient building block for the construction of various heterocycles and it is assumed to be an intermediate in different three-component reactions. Here, we present the results of XRD of (<b>1)</b> demonstrating the lin...

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Bibliographic Details
Main Authors: Vyacheslav S. Grinev, Ilya A. Demeshko, Anna E. Sklyar, Alevtina Yu. Yegorova
Format: Article
Language:English
Published: MDPI AG 2023-11-01
Series:Chemistry Proceedings
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Online Access:https://www.mdpi.com/2673-4583/14/1/10
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Summary:2-(Ethoxymethylene)malononitrile (<b>1)</b> is a very convenient building block for the construction of various heterocycles and it is assumed to be an intermediate in different three-component reactions. Here, we present the results of XRD of (<b>1)</b> demonstrating the linkage of the co-oriented molecules in crystal via C-H···N≡C non-covalent interactions. To evaluate the energy of such interactions, we conducted DFT simulations. The molecules of (<b>1)</b> are linked into infinite chains via C-H···N≡C close contacts with a distance of 2.494 Å. When performing theoretical measurements of the energy of H···N non-covalent interactions by DFT, it was determined by the M06-2X functional, equal to −1.20 kcal/mol, meaning weak attraction.
ISSN:2673-4583