Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution

Cornelia Uncuta, Emeric Bartha, Dragos Gherase, Ioan Andrei Loas, Florina Teodorescu, Richard A. Varga, Nicolas Vanthuyne, Christian Roussel, Ulf Berg

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskriftPeer review

2 Citeringar (SciVal)

Sammanfattning

A homologous series of chiral bis-ketals and mixed hemiketal-ketals with rigid bicyclo[3.3.1]-3,7-dioxanonane skeleton has been prepared. The crystallization mode (conglomerate or racemic compound) was established by chiral HPLC with double UV/polarimetric detection. The study of the solid-state structure by single crystal X-ray diffraction disclosed interesting CH ... pi intermolecular interactions. Hindering of rotation of phenyl groups at (hemi)ketalic centres was found to occur. A H-1-DNMR study gave activation barriers Delta G(#) of 15.9 kcal mol(-1) in the ketalic moiety and 10.3 kcal mol(-1) in the hemiketalic moiety. The experimental results were substantiated by MM and OFT calculations for ground and transition states. (c) 2011 Published by Elsevier B.V.
Originalspråkengelska
Sidor (från-till)20-30
TidskriftJournal of Molecular Structure
Volym989
Utgåva1-3
DOI
StatusPublished - 2011

Bibliografisk information

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Ämnesklassifikation (UKÄ)

  • Organisk kemi

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