Next Article in Journal
High-Pressure Reactivity of Kr and F2—Stabilization of Krypton in the +4 Oxidation State
Previous Article in Journal
Indentation Plasticity and Fracture Studies of Organic Crystals
Article Menu
Issue 11 (November) cover image

Export Article

Open AccessCommunication
Crystals 2017, 7(11), 327; doi:10.3390/cryst7110327

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
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)
View Full-Text   |   Download PDF [5171 KB, uploaded 27 November 2017]   |  

Abstract

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
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Crystals EISSN 2073-4352 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top