Next Article in Journal
Ion-Trap Mass Spectrometric Analysis of Bisphenol A Interactions With Titanium Dioxide Nanoparticles and Milk Proteins
Next Article in Special Issue
Regioselective and Stereodivergent Synthesis of Enantiomerically Pure Vic-Diamines from Chiral β-Amino Alcohols with 2-Pyridyl and 6-(2,2′-Bipyridyl) Moieties
Previous Article in Journal
Digital PCR as an Emerging Tool for Monitoring of Microbial Biodegradation
Previous Article in Special Issue
Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry
Open AccessArticle

Trityl-Containing Alcohols—An Efficient Chirality Transmission Process from Inductor to the Stereodynamic Propeller and their Solid-State Structural Diversity

1
Department of Chemistry Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61614 Poznań, Poland
2
Centre for Advanced Technologies Adam Mickiewicz University, Uniwersytetu Poznańskiego 10, 61614 Poznań, Poland
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(3), 707; https://doi.org/10.3390/molecules25030707
Received: 15 January 2020 / Revised: 3 February 2020 / Accepted: 4 February 2020 / Published: 6 February 2020
(This article belongs to the Special Issue Stereochemistry in Action)
The cascade process of a dynamic chirality transmission from the permanent chirality center to the stereodynamic triphenylmethyl group has been studied for series of optically active trityl derivatives. The structural analysis, carried out with the use of complementary methods, enabled us to determine the mechanism of chirality transfer. The process of chirality transmission involves a set of weak but complementary electrostatic interactions. The induction of helicity in a trityl propeller is revealed by rising non-zero cotton effects in the area of trityl UV-absorption. The presence of an additional stereogenic center in close proximity to the trityl-containing stereogenic center significantly affects the sign and, to a lesser extent, magnitude of the respective cotton effects. Despite the bulkiness of the trityl, in the crystalline phase, the molecules under study strictly fill the space. In the crystal, molecules form aggregates stabilized by OH•••O hydrogen bonds. However, the presence of two trityl groups precludes formation of OH•••O hydrogen bonding. Additionally, the trityl group seems to be responsible for the formation of the solid solutions by e.g., racemates of trans- and cis-2-tritylcyclohexanol. Therefore, the trityl group acts as a supramolecular protective group, which in turn can be used in the crystal engineering. View Full-Text
Keywords: chirality transmission; induced circular dichroism; stereoselective synthesis; trityl chirality transmission; induced circular dichroism; stereoselective synthesis; trityl
Show Figures

Figure 1

MDPI and ACS Style

Górczyńska, S.; Brzdonkiewicz, A.; Jelecki, M.; Czapik, A.; Stasiak, B.; Kwit, M. Trityl-Containing Alcohols—An Efficient Chirality Transmission Process from Inductor to the Stereodynamic Propeller and their Solid-State Structural Diversity. Molecules 2020, 25, 707.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop