Synthesis of Iodinated Thiazolo[2,3-a]isoquinolinium Salts and Their Crystal Strucutres with/without Halogen Bond

Matsumoto, Shoji; Sumida, Ryuta; Tan, Sia Er; Akazome, Motohiro

doi:10.3987/com-18-s(t)47

Cited by 4 publications

(2 citation statements)

References 25 publications

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“…The use of such heterocyclic systems as thiazolo [2,3-a]isoquinolinium cations [40] is very promising in this regard. Syntheses of the related systems, such as 2H-benzo [4,5]thiazolo [2,3-b] [1,3] thiazin-5-ium, are superficially described in the literature [41], and only a few examples of 3,5,6,7-tetrahydro-2H-thiazolo [2,3-b] [1,3]thiazin-4-ium synthesis and transformation have been described [42][43][44] in the context of their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Noncovalent Bonds, Spectral and Thermal Properties of Substituted Thiazolo[2,3-b][1,3]thiazinium Triiodides

et al. 2019

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The interrelation between noncovalent bonds and physicochemical properties is in the spotlight due to the practical aspects in the field of crystalline material design. Such study requires a number of similar substances in order to reveal the effect of structural features on observed properties. For this reason, we analyzed a series of three substituted thiazolo[2,3-b][1,3]thiazinium triiodides synthesized by an iodocyclization reaction. They have been characterized with the use of X-ray diffraction, Raman spectroscopy, and thermal analysis. Various types of noncovalent interactions have been considered, and an S…I chalcogen bond type has been confirmed using the electronic criterion based on the calculated electron density and electrostatic potential. The involvement of triiodide anions in the I…I halogen and S…I chalcogen bonding is reflected in the Raman spectroscopic properties of the I–I bonds: identical bond lengths demonstrate different wave numbers of symmetric triiodide vibration and different values of electron density at bond critical points. Chalcogen and halogen bonds formed by the terminal iodine atom of triiodide anion and numerous cation…cation pairwise interactions can serve as one of the reasons for increased thermal stability and retention of iodine in the melt under heating.

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Section: Introductionmentioning

confidence: 99%

Noncovalent Bonds, Spectral and Thermal Properties of Substituted Thiazolo[2,3-b][1,3]thiazinium Triiodides

et al. 2019

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“…A CSD search revealed only six hits for any pyridinium-1vinyl-1-ether fragment (CSD Version 5.43, Update 4, November 2022; Groom et al, 2016). Of these, five were of substituted isoquinolinium salts, where the vinyl group of the searched fragment corresponds to a C C bond in a thiazole ring fused to the substituted isoquinoline, making them largely unrelated to the title compound (Matsumoto et al, 2018(Matsumoto et al, , 2022. The remaining hit is the related compound and precursor material, I, 2-chloro-1-(1-ethyoxyethenyl)pyridin-1ium trifluoromethanesulfonate, CSD refcode JETTOU (Shapiro et al, 2018).…”

Section: Database Surveymentioning

confidence: 99%

Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate

Krevlin,

Bote,

Crespo

et al. 2023

Acta Cryst E

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The novel bench-stable N-quaternized ketene N,O-acetal, C16H19N2O+·CF3O3S−, was synthesized and its structure determined. The title compound is a rare example of a pyridinium ketene hemiaminal for which a crystal structure has been determined, joining the 2-chloro-1-(1-ethyoxyethenyl)pyridin-1-ium trifluoromethanesulfonate salt from which it was synthesized. The cationic species of the title compound can be defined by three individually planar fragments assembling into a non-coplanar cation. The phenyl substituent extending from the amino nitrogen atom and the ethyoxyvinyl substituent extending from the pyridine N atom are oriented on the same side of the molecule and maintain the closest coplanar relationship of the three fragments. Supramolecular interactions are dominated by C—H...O interactions from the cation to the SO3 side of the trifluoromethanesulfonate anion, forming a two-dimensional substructure.

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Relationship between halogen-halogen interaction and electric conductivity in thiazolo[2,3-a]isoquinolin-7-ium triiodides

Matsumoto

Sumida

Akazome

2022

Journal of Molecular Structure

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Synthesis of Iodinated Thiazolo[2,3-a]isoquinolinium Salts and Their Crystal Strucutres with/without Halogen Bond

Cited by 4 publications

References 25 publications

Noncovalent Bonds, Spectral and Thermal Properties of Substituted Thiazolo[2,3-b][1,3]thiazinium Triiodides

Noncovalent Bonds, Spectral and Thermal Properties of Substituted Thiazolo[2,3-b][1,3]thiazinium Triiodides

Synthesis and crystal structure of a bench-stable pyridinium ketene hemiaminal: 1-(1-ethoxyethenyl)-2-[methyl(phenyl)amino]pyridin-1-ium trifluoromethanesulfonate

Relationship between halogen-halogen interaction and electric conductivity in thiazolo[2,3-a]isoquinolin-7-ium triiodides

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