Enantiotropy of simvastatin as a result of weakened interactions in the crystal lattice: entropy-driven double transitions and the transient modulated phase as seen by solid-state NMR spectroscopy
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F22%3A00552594" target="_blank" >RIV/61389013:_____/22:00552594 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22340/22:43924665
Result on the web
<a href="https://www.mdpi.com/1420-3049/27/3/679" target="_blank" >https://www.mdpi.com/1420-3049/27/3/679</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules27030679" target="_blank" >10.3390/molecules27030679</a>
Alternative languages
Result language
angličtina
Original language name
Enantiotropy of simvastatin as a result of weakened interactions in the crystal lattice: entropy-driven double transitions and the transient modulated phase as seen by solid-state NMR spectroscopy
Original language description
In crystalline molecular solids, in the absence of strong intermolecular interactions, entropy-driven processes play a key role in the formation of dynamically modulated transient phases. Specifically, in crystalline simvastatin, the observed fully reversible enantiotropic behavior is associated with multiple order–disorder transitions: upon cooling, the dynamically disordered high-temperature polymorphic Form I is transformed to the completely ordered low-temperature polymorphic Form III via the intermediate (transient) modulated phase II. This behavior is associated with a significant reduction in the kinetic energy of the rotating and flipping ester substituents, as well as a decrease in structural ordering into two distinct positions. In transient phase II, the conventional three-dimensional structure is modulated by periodic distortions caused by cooperative conformation exchange of the ester substituent between the two states, which is enabled by weakened hydrogen bonding. Based on solid-state NMR data analysis, the mechanism of the enantiotropic phase transition and the presence of the transient modulated phase are documented.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
<a href="/en/project/LTAUSA18011" target="_blank" >LTAUSA18011: Ab Initio Investigation of Polymorphism of Active Pharmaceutical Ingredients Supported by State of the Art NMR Crystallographic and Calorimetric Experiments.</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Molecules
ISSN
1420-3049
e-ISSN
1420-3049
Volume of the periodical
27
Issue of the periodical within the volume
3
Country of publishing house
CH - SWITZERLAND
Number of pages
18
Pages from-to
679
UT code for WoS article
000759813400001
EID of the result in the Scopus database
2-s2.0-85123103085