Synthesis, X-ray and DFT Studies of 6-halo-3--ones

The Richter cyclization was used for the synthesis of 6-halo-3-(hydroxymethyl)cinnolin-4(1H)-ones. X-ray analysis revealed that these compounds exist as dimers in their crystal state, wherein two molecules are linked by intermolecular double and bifurcated hydrogen bonds that can explain their low s...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022-09, Vol.58 (8-9), p.432
Main Authors: Babushkina, Anastasia A, Mikhaylov, Vladimir N, Novikov, Alexander S, Sorokoumov, Viktor N, Gureev, Maxim A, Kryukova, Mariya A, Shpakov, Alexander O
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Hydrogen
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container_issue 8-9
container_start_page 432
container_title Chemistry of heterocyclic compounds (New York, N.Y. 1965)
container_volume 58
creator Babushkina, Anastasia A
Mikhaylov, Vladimir N
Novikov, Alexander S
Sorokoumov, Viktor N
Gureev, Maxim A
Kryukova, Mariya A
Shpakov, Alexander O
description The Richter cyclization was used for the synthesis of 6-halo-3-(hydroxymethyl)cinnolin-4(1H)-ones. X-ray analysis revealed that these compounds exist as dimers in their crystal state, wherein two molecules are linked by intermolecular double and bifurcated hydrogen bonds that can explain their low solubility. Theoretical study of bifurcated hydrogen bonds responsible for the dimerization was carried out by DFT calculations as well as by topological analysis of the electron density distribution within the framework of Bader's theory.
doi_str_mv 10.1007/s10593-022-03109-3
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title Synthesis, X-ray and DFT Studies of 6-halo-3--ones
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