A Crystalline Dimeric Steroidal Diboronate with Electronically Impeded Rotation
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F23%3A00566053" target="_blank" >RIV/61388955:_____/23:00566053 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/23:00566053
Result on the web
<a href="https://hdl.handle.net/11104/0337490" target="_blank" >https://hdl.handle.net/11104/0337490</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c01676" target="_blank" >10.1021/acs.joc.2c01676</a>
Alternative languages
Result language
angličtina
Original language name
A Crystalline Dimeric Steroidal Diboronate with Electronically Impeded Rotation
Original language description
The dimeric steroid SMR-3, featuring a 1,4-phenyldiboronic ester flanked by two pregnan-triol frameworks, was synthesized to explore the intramolecular dynamics of its central component. The structural data from single-crystal X-ray diffraction studies and the Hirshfeld analyses indicate small steric effects around the aromatic ring that should favor the intended motion. However, solid-state NMR data obtained through VT 13C{1H} CPMAS and 2H spin-echo experiments, using the deuterated analogue SMR-3D4, revealed that this component is rigid even at temperatures where other reported steroidal molecular rotors experience fast rotation (85 °C). A combination of classical molecular dynamics, molecular mechanics, and correlated ab initio calculations allowed us to distinguish the steric and electronic factors that restrict the potential motion in this compound. The experimental and computational data reveal that electronic components dominate the behavior and are responsible for the high rotational barrier in the SMR-3 crystal.
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/GA20-01472S" target="_blank" >GA20-01472S: NMR crystallography of disordered systems</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
88
Issue of the periodical within the volume
1
Country of publishing house
US - UNITED STATES
Number of pages
11
Pages from-to
49-59
UT code for WoS article
000894953200001
EID of the result in the Scopus database
2-s2.0-85143871301