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Protection function of the trityl group in supramolecular systems formed by chiral triphenylacetic acid amides

Wioletta Bendzińska-Berus

Abstract

The thesis presents the results of the X-ray investigations crystal structures of chiral derivatives of triphenylacetamide. The work has concentrated on the ability of the trityl group to hinder the proton donor ability of the neighboring amide NH functionality and the influence of this phenomenon on the intra- and intermolecular interactions in crystals. Analysis of a relatively high crystal population allowed to establish conditions necessary to reactivate the NH proton donor function. This takes place upon inclusion of solvent molecules that possess strong hydrogen bond acceptors or by inserting an extra spacer between the trityl and amide functionalities. The thesis also concerned a possibility of transmitting information from the stereogenic center to the trityl receiver. It has been postulated that information is transmitted through a system of weak intramolecular hydrogen bonds and dipolar interactions. It has been established that trityl group maintains its helical conformation in crystals, despite the presence of two such groups in vicinal positions in a molecule. The conditions leading to a significant deformation of the trityl propeller has been established.
Record ID
UAM910a4d12d837421b9e1d317581b532d1
Diploma type
Doctor of Philosophy
Author
Title in Polish
Funkcja blokująca grupy trytylowej w układach supramolekularnych tworzonych przez chiralne amidy kwasu trifenylooctowego
Title in English
Protection function of the trityl group in supramolecular systems formed by chiral triphenylacetic acid amides
Language
pol (pl) Polish
Certifying Unit
Wydział Chemii [nowa struktura organizacyjna] (SNŚ/WC)
Scientific discipline (2.0)
6.5 chemical sciences
Status
Finished
Year of creation
2018
Defense Date
11-06-2018
Title date
11-06-2018
Supervisor
Urszula Rychlewska Urszula Rychlewska,, Wydział Chemii [nowa struktura organizacyjna] (SNŚ/WC)Szkoła Nauk Ścisłych [nowa struktura organizacyjna] (SNŚ)
URL
http://hdl.handle.net/10593/23552 Opening in a new tab
Keywords in English
X-ray analysis, inclusion compounds, trityl group, steric hindrance, chirality
Abstract in English
The thesis presents the results of the X-ray investigations crystal structures of chiral derivatives of triphenylacetamide. The work has concentrated on the ability of the trityl group to hinder the proton donor ability of the neighboring amide NH functionality and the influence of this phenomenon on the intra- and intermolecular interactions in crystals. Analysis of a relatively high crystal population allowed to establish conditions necessary to reactivate the NH proton donor function. This takes place upon inclusion of solvent molecules that possess strong hydrogen bond acceptors or by inserting an extra spacer between the trityl and amide functionalities. The thesis also concerned a possibility of transmitting information from the stereogenic center to the trityl receiver. It has been postulated that information is transmitted through a system of weak intramolecular hydrogen bonds and dipolar interactions. It has been established that trityl group maintains its helical conformation in crystals, despite the presence of two such groups in vicinal positions in a molecule. The conditions leading to a significant deformation of the trityl propeller has been established.
Thesis file
  • File: 1
    Praca doktorska_W.Bendzińska-Berus.pdf
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Uniform Resource Identifier
https://researchportal.amu.edu.pl/info/phd/UAM910a4d12d837421b9e1d317581b532d1/
URN
urn:amu-prod:UAM910a4d12d837421b9e1d317581b532d1

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