Object's details: Oxidation of 2-mercaptopyridine N-oxide upon iodine agent: structural and FT-IR studies on charge-assisted hydrogen bonds CAHB(+) and I…I halogen interactions in 2,2′-dithiobis(pyridine N-oxide) ionic cocrystal

Provider:Repozytorium Uniwersytetu Łódzkiego

Description

Title:
Oxidation of 2-mercaptopyridine N-oxide upon iodine agent: structural and FT-IR studies on charge-assisted hydrogen bonds CAHB(+) and I…I halogen interactions in 2,2′-dithiobis(pyridine N-oxide) ionic cocrystal
Creator:
Wzgarda-Raj, Kinga;
Rybarczyk-Pirek, Agnieszka;
Palusiak, Marcin;
Wojtulewski, S.;
Pindelska, E.
Contributor:
Group of Theoretical and Structural Chemistry, Department of Physical Chemistry, Faculty of Chemistry, University of Łódź, Pomorska 163/165, 90-236 Łódź, Poland;
Department of Theoretical Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland;
Faculty of Pharmacy, Laboratory of Medicine Division, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, Poland
Description:
2-Mercaptopyridine N-oxide (I) undergoes spontaneous dimerization to the disulfide form due to reaction with iodine acting as an oxidizing reagent. As a result, a di-N-oxide disulfide derivative of pyridine is obtained. During the process of crystallization, one of N-oxide groups undergoes protonation and a cation form of disulfide moiety cocrystallizes with I3 − counterion forming a salt structure. Therefore, in the crystalline state, the 2,2′-dithiobis(pyridine N-oxide) molecule exists in a not observed previously form of monocation. Interestingly, the protonated N-oxide group does not form hydrogen-bonded salt bridges (of the CAHB(±) type with I3 − anions) but prefers to be involved in intermolecular interactions with the unprotonated N-oxide group of the adjacent molecule This results in formation of intermolecular CAHB(+) hydrogen bridges finally linking molecules into infinite chains. The crystal structure is also stabilized by other various noncovalent interactions, including iodine...iodine and sulfur...iodine contacts.
Object availability:
free access
Rights:
Uznanie autorstwa 4.0 Międzynarodowe;
http://creativecommons.org/licenses/by/4.0
Date:
2021.08.31;
2019
Type:
Article
Language:
English
Format:
application/pdf
Publisher:
Springer Nature
Relation:
Structural Chemistry;30
Subject:
Mercaptopyridine N-oxide;
Pyridinethione;
Iodine;
Crystal structure;
Disulfide;
FT-IR studies
Identifier:
Wzgarda-Raj, K., Rybarczyk-Pirek, A.J., Wojtulewski, S. et al. Oxidation of 2-mercaptopyridine N-oxide upon iodine agent: structural and FT-IR studies on charge-assisted hydrogen bonds CAHB(+) and I…I halogen interactions in 2,2′-dithiobis(pyridine N-oxide) ionic cocrystal. Struct Chem 30, 827–833 (2019). https://doi.org/10.1007/s11224-019-1290-x;
1040-0400;
http://hdl.handle.net/11089/38963 ;
1572-9001;
10.1007/s11224-019-1290-x
Data provider:
Repozytorium Uniwersytetu Łódzkiego

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Object's details: Oxidation of 2-mercaptopyridine N-oxide upon iodine agent: structural and FT-IR studies on charge-assisted hydrogen bonds CAHB(+) and I…I halogen interactions in 2,2′-dithiobis(pyridine N-oxide) ionic cocrystal

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