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

1
National University of Science and Technology «MISIS», Moscow 119049, Russian Federation
2
Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119992, Russian Federation
3
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation
4
Kazan National Research Technological University, Kazan 420015, Russian Federation
5
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Lisbon 1049–001, Portugal
6
Department of Chemistry, Baku State University, Baku AZ1148, Azerbaijan
*
Authors to whom correspondence should be addressed.
Academic Editor: Helmut Cölfen
Crystals 2017, 7(11), 327; https://doi.org/10.3390/cryst7110327
Received: 9 October 2017 / Revised: 24 October 2017 / Accepted: 26 October 2017 / Published: 28 October 2017
(This article belongs to the Special Issue Chalcogen Bonding in Crystalline and Catalyst Materials)
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. View Full-Text
Keywords: noncovalent interactions; tetrel bonding; chalcogen bonding; charge-assisted hydrogen bonding noncovalent interactions; tetrel bonding; chalcogen bonding; charge-assisted hydrogen bonding
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Guseinov, F.I.; Pistsov, M.F.; Movsumzade, E.M.; Kustov, L.M.; Tafeenko, V.A.; Chernyshev, V.V.; Gurbanov, A.V.; Mahmudov, K.T.; Pombeiro, A.J.L. Tetrel, Chalcogen, and Charge-Assisted Hydrogen Bonds in 2-((2-Carboxy-1-(substituted)-2-hydroxyethyl)thio) Pyridin-1-ium Chlorides. Crystals 2017, 7, 327.

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