Tyramine as a prolific coformer in crystal engineering : insights from classical crystal structure analysis and electron density studies

2025
journal article
article
1
dc.abstract.enProlific coformers are compounds that readily form multicomponent crystals with diverse partners, playing a crucial role in crystal engineering by enabling the creation of new solids with enhanced physicochemical properties. In this study, we investigated tyramine as a potentially attractive cocrystallization component, given its reported ability in the Cambridge Structural Database (CSD) to interact with over 60 diverse building blocks. We conducted classical crystal structure and charge density analyses, along with Hirshfeld surface studies, on three distinct tyramine organic salts with L-pyroglutamic acid, D-mandelic acid, and p-aminohippuric acid. This work aimed to determine whether and why tyramine can be considered a prolific coformer. Tyramine cations were evaluated in terms of similarities and differences in intermolecular interactions across these salts. Additionally, we examined the conformation of the aliphatic chain and $ΔpK_{a}$ values for all tyramine salts in the CSD to identify the most significant factors influencing cocrystallization with tyramine. Our findings suggest that proton transfer is a crucial factor in the formation of stable multicomponent materials with tyramine. Furthermore, the selection of coformers for cocrystallization with tyramine should prioritize repeatable synthons, particularly those containing carboxylic groups.
dc.affiliationSzkoła Doktorska Nauk Ścisłych i Przyrodniczych
dc.affiliationWydział Chemii : Zakład Krystalochemii i Krystalofizyki
dc.contributor.authorGrabowski, Szymon - 370479
dc.contributor.authorGryl, Marlena - 141879
dc.date.accession2025-01-28
dc.date.accessioned2025-01-28T13:57:36Z
dc.date.available2025-01-28T13:57:36Z
dc.date.createdat2025-01-23T15:25:28Zen
dc.date.issued2025
dc.date.openaccess0
dc.description.accesstimew momencie opublikowania
dc.description.number1
dc.description.physical109-119
dc.description.versionostateczna wersja wydawcy
dc.description.volume25
dc.identifier.doi10.1021/acs.cgd.4c00834
dc.identifier.eissn1528-7505
dc.identifier.issn1528-7483
dc.identifier.urihttps://ruj.uj.edu.pl/handle/item/546383
dc.identifier.weblinkhttps://pubs.acs.org/doi/10.1021/acs.cgd.4c00834
dc.languageeng
dc.language.containereng
dc.rightsUdzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa
dc.rights.licenceCC-BY
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/legalcode.pl
dc.share.typeinne
dc.subtypeArticle
dc.titleTyramine as a prolific coformer in crystal engineering : insights from classical crystal structure analysis and electron density studies
dc.title.journalCrystal Growth & Design
dc.typeJournalArticle
dspace.entity.typePublicationen
dc.abstract.en
Prolific coformers are compounds that readily form multicomponent crystals with diverse partners, playing a crucial role in crystal engineering by enabling the creation of new solids with enhanced physicochemical properties. In this study, we investigated tyramine as a potentially attractive cocrystallization component, given its reported ability in the Cambridge Structural Database (CSD) to interact with over 60 diverse building blocks. We conducted classical crystal structure and charge density analyses, along with Hirshfeld surface studies, on three distinct tyramine organic salts with L-pyroglutamic acid, D-mandelic acid, and p-aminohippuric acid. This work aimed to determine whether and why tyramine can be considered a prolific coformer. Tyramine cations were evaluated in terms of similarities and differences in intermolecular interactions across these salts. Additionally, we examined the conformation of the aliphatic chain and $ΔpK_{a}$ values for all tyramine salts in the CSD to identify the most significant factors influencing cocrystallization with tyramine. Our findings suggest that proton transfer is a crucial factor in the formation of stable multicomponent materials with tyramine. Furthermore, the selection of coformers for cocrystallization with tyramine should prioritize repeatable synthons, particularly those containing carboxylic groups.
dc.affiliation
Szkoła Doktorska Nauk Ścisłych i Przyrodniczych
dc.affiliation
Wydział Chemii : Zakład Krystalochemii i Krystalofizyki
dc.contributor.author
Grabowski, Szymon - 370479
dc.contributor.author
Gryl, Marlena - 141879
dc.date.accession
2025-01-28
dc.date.accessioned
2025-01-28T13:57:36Z
dc.date.available
2025-01-28T13:57:36Z
dc.date.createdaten
2025-01-23T15:25:28Z
dc.date.issued
2025
dc.date.openaccess
0
dc.description.accesstime
w momencie opublikowania
dc.description.number
1
dc.description.physical
109-119
dc.description.version
ostateczna wersja wydawcy
dc.description.volume
25
dc.identifier.doi
10.1021/acs.cgd.4c00834
dc.identifier.eissn
1528-7505
dc.identifier.issn
1528-7483
dc.identifier.uri
https://ruj.uj.edu.pl/handle/item/546383
dc.identifier.weblink
https://pubs.acs.org/doi/10.1021/acs.cgd.4c00834
dc.language
eng
dc.language.container
eng
dc.rights
Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa
dc.rights.licence
CC-BY
dc.rights.uri
http://creativecommons.org/licenses/by/4.0/legalcode.pl
dc.share.type
inne
dc.subtype
Article
dc.title
Tyramine as a prolific coformer in crystal engineering : insights from classical crystal structure analysis and electron density studies
dc.title.journal
Crystal Growth & Design
dc.type
JournalArticle
dspace.entity.typeen
Publication
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