Tetrel, Chalcogen, and Charge-Assisted Hydrogen Bonds in 2-((2-Carboxy-1-(substituted)-2-hydroxyethyl)thio) Pyridin-1-ium Chlorides

Reaction of 2-chloro-2-(diethoxymethyl)-3-substitutedoxirane or 1-chloro-1-(substituted) -3,3-diethoxypropan-2-one with pyridine-2-thiol in EtOH at 25 °C yields 3-(diethoxymethyl)-3-hydroxy-2-substituted-2,3-dihydrothiazolo[3,2-a]pyridin-4-ium chlorides, which subsequently, in MeCN at 85°C, transfor...

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Published inCrystals (Basel) Vol. 7; no. 11; p. 327
Main Authors Guseinov, Firudin, Pistsov, Mikhail, Movsumzade, Eldar, Kustov, Leonid, Tafeenko, Victor, Chernyshev, Vladimir, Gurbanov, Atash, Mahmudov, Kamran, Pombeiro, Armando
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.11.2017
Subjects
chalcogen bonding
charge-assisted hydrogen bonding
Chemical bonds
Chlorides
Hydrogen bonds
Hydrogen storage
noncovalent interactions
Substitutes
tetrel bonding
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Summary:Reaction of 2-chloro-2-(diethoxymethyl)-3-substitutedoxirane or 1-chloro-1-(substituted) -3,3-diethoxypropan-2-one with pyridine-2-thiol in EtOH at 25 °C yields 3-(diethoxymethyl)-3-hydroxy-2-substituted-2,3-dihydrothiazolo[3,2-a]pyridin-4-ium chlorides, which subsequently, in MeCN at 85°C, transforms into ring-opening products, 2-((2-carboxy-1-(substituted) -2-hydroxyethyl)thio)pyridin-1-ium chlorides. The tetrel (C•••O) and chalcogen (S•••O) bonds are found in the structures of 5 and 6, respectively. Compound 6 is also present in halogen bonding with a short O•••Cl distance (3.067 Å). Both molecules are stabilized in crystal by tetrel, chalcogen, and multiple charge-assisted hydrogen bonds.
ISSN:2073-4352
2073-4352
DOI:10.3390/cryst7110327