{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,26]],"date-time":"2026-04-26T09:22:28Z","timestamp":1777195348570,"version":"3.51.4"},"reference-count":32,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2017,10,28]],"date-time":"2017-10-28T00:00:00Z","timestamp":1509148800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Crystals"],"abstract":"<jats:p>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 \u00b0C yields 3-(diethoxymethyl)-3-hydroxy-2-substituted-2,3-dihydrothiazolo[3,2-a]pyridin-4-ium chlorides, which subsequently, in MeCN at 85\u00b0C, transforms into ring-opening products, 2-((2-carboxy-1-(substituted) -2-hydroxyethyl)thio)pyridin-1-ium chlorides. The tetrel (C\u00b7\u00b7\u00b7O) and chalcogen (S\u00b7\u00b7\u00b7O) bonds are found in the structures of 5 and 6, respectively. Compound 6 is also present in halogen bonding with a short O\u00b7\u00b7\u00b7Cl distance (3.067 \u00c5). Both molecules are stabilized in crystal by tetrel, chalcogen, and multiple charge-assisted hydrogen bonds.<\/jats:p>","DOI":"10.3390\/cryst7110327","type":"journal-article","created":{"date-parts":[[2017,10,30]],"date-time":"2017-10-30T12:16:23Z","timestamp":1509365783000},"page":"327","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Tetrel, Chalcogen, and Charge-Assisted Hydrogen Bonds in 2-((2-Carboxy-1-(substituted)-2-hydroxyethyl)thio) Pyridin-1-ium Chlorides"],"prefix":"10.3390","volume":"7","author":[{"given":"Firudin","family":"Guseinov","sequence":"first","affiliation":[{"name":"National University of Science and Technology \u00abMISIS\u00bb, Moscow 119049, Russian Federation"},{"name":"Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119992, Russian Federation"},{"name":"N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation"}]},{"given":"Mikhail","family":"Pistsov","sequence":"additional","affiliation":[{"name":"Kazan National Research Technological University, Kazan 420015, Russian Federation"}]},{"given":"Eldar","family":"Movsumzade","sequence":"additional","affiliation":[{"name":"National University of Science and Technology \u00abMISIS\u00bb, Moscow 119049, Russian Federation"},{"name":"N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation"}]},{"given":"Leonid","family":"Kustov","sequence":"additional","affiliation":[{"name":"National University of Science and Technology \u00abMISIS\u00bb, Moscow 119049, Russian Federation"},{"name":"Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119992, Russian Federation"},{"name":"N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation"}]},{"given":"Victor","family":"Tafeenko","sequence":"additional","affiliation":[{"name":"Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119992, Russian Federation"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8514-7471","authenticated-orcid":false,"given":"Vladimir","family":"Chernyshev","sequence":"additional","affiliation":[{"name":"Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow 119992, Russian Federation"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1415-8012","authenticated-orcid":false,"given":"Atash","family":"Gurbanov","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Lisbon 1049\u2013001, Portugal"},{"name":"Department of Chemistry, Baku State University, Baku AZ1148, Azerbaijan"}]},{"given":"Kamran","family":"Mahmudov","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Lisbon 1049\u2013001, Portugal"},{"name":"Department of Chemistry, Baku State University, Baku AZ1148, Azerbaijan"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Lisbon 1049\u2013001, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,10,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"689","DOI":"10.1007\/s00894-008-0279-y","article-title":"Why are dimethyl sulfoxide and dimethyl sulfone such good solvents","volume":"14","author":"Clark","year":"2008","journal-title":"J. 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