KFU. Card publication. The second example of doubly enantiophobic behavior during crystallization: a detailed crystallographic, thermochemical and spectroscopic study

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THE SECOND EXAMPLE OF DOUBLY ENANTIOPHOBIC BEHAVIOR DURING CRYSTALLIZATION: A DETAILED CRYSTALLOGRAPHIC, THERMOCHEMICAL AND SPECTROSCOPIC STUDY

Form of presentation

Articles in international journals and collections

Year of publication

2021

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Authors, employees of KFU

Kurbangalieva Almira Rafaelovna, author

Lodochnikova Olga Aleksandrovna, author

Other authors

Gerasimova Darya , author

Zakharychev Dmitriy , author

Sayfina Alina , author

Fayzullin Robert , author

Bibliographic description in the original language

Gerasimova, D. P. The second example of doubly enantiophobic behavior during crystallization: a detailed crystallographic, thermochemical and spectroscopic study / D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, R. R. Fayzullin, A. R. Kurbangalieva, O. A. Lodochnikova // CrystEngComm. – 2021. – V. 23, � 21. – R. 3907–3918.

Annotation

Herein we have found a second example of doubly enantiophobic behavior during the crystallization of rac-1-benzyl-3-chloro-4-[(4-chlorophenyl)sulfanyl]-5-hydroxy-1,5-dihydro-2H-pyrrol-2-one, i.e., the formation of two conglomerates with different crystal structures in the absence of any racemic compounds. In both polymorphic modifications, the main supramolecular motif is appeared to be a hydrogen-bonded chain or helix of different symmetry, which is related to an α-hydroxyamide chain synthon. Additional crosslinking of the homochiral chains in the crystals of both crystalline forms, which is realized through weak, noncovalent interactions, can be a probable reason for the reproducibility and stability of the α-hydroxyamide chain synthon and polymorphic diversity registered. It was shown that each of the conglomerates is thermodynamically stable in certain temperature ranges. For the first time, a binary phase diagram for the chiral system complicated by an enantiotropic phase transition is reconstructed based on experimental data, which is characterized by the presence of a thermodynamic stability permutation line between the two racemic conglomerates.

Keywords

doubly enantiophobic behavior, 1,5-dihydro-2H-pyrrol-2-one, conglomerates

The name of the journal

CRYSTENGCOMM

URL

http://pubs.rsc.org/en/content/articlelanding/2021/ce/d1ce00227a

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=253585&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Kurbangalieva Almira Rafaelovna	ru_RU
dc.contributor.author	Lodochnikova Olga Aleksandrovna	ru_RU
dc.contributor.author	Gerasimova Darya	ru_RU
dc.contributor.author	Zakharychev Dmitriy	ru_RU
dc.contributor.author	Sayfina Alina	ru_RU
dc.contributor.author	Fayzullin Robert	ru_RU
dc.date.accessioned	2021-01-01T00:00:00Z	ru_RU
dc.date.available	2021-01-01T00:00:00Z	ru_RU
dc.date.issued	2021	ru_RU
dc.identifier.citation	Gerasimova, D. P. The second example of doubly enantiophobic behavior during crystallization: a detailed crystallographic, thermochemical and spectroscopic study / D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, R. R. Fayzullin, A. R. Kurbangalieva, O. A. Lodochnikova // CrystEngComm. – 2021. – V. 23, � 21. – �. 3907–3918.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=253585&p_lang=2	ru_RU
dc.description.abstract	CRYSTENGCOMM	ru_RU
dc.description.abstract	Herein we have found a second example of doubly enantiophobic behavior during the crystallization of rac-1-benzyl-3-chloro-4-[(4-chlorophenyl)sulfanyl]-5-hydroxy-1,5-dihydro-2H-pyrrol-2-one, i.e., the formation of two conglomerates with different crystal structures in the absence of any racemic compounds. In both polymorphic modifications, the main supramolecular motif is appeared to be a hydrogen-bonded chain or helix of different symmetry, which is related to an α-hydroxyamide chain synthon. Additional crosslinking of the homochiral chains in the crystals of both crystalline forms, which is realized through weak, noncovalent interactions, can be a probable reason for the reproducibility and stability of the α-hydroxyamide chain synthon and polymorphic diversity registered. It was shown that each of the conglomerates is thermodynamically stable in certain temperature ranges. For the first time, a binary phase diagram for the chiral system complicated by an enantiotropic phase transition is reconstructed based on experimental data, which is characterized by the presence of a thermodynamic stability permutation line between the two racemic conglomerates.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	doubly enantiophobic behavior	ru_RU
dc.subject	1	ru_RU
dc.subject	5-dihydro-2H-pyrrol-2-one	ru_RU
dc.subject	conglomerates	ru_RU
dc.title	The second example of doubly enantiophobic behavior during crystallization: a detailed crystallographic, thermochemical and spectroscopic study	ru_RU
dc.type	Articles in international journals and collections	ru_RU