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

Uncuta, Cornelia ; Bartha, Emeric ; Gherase, Dragos ; Loas, Ioan Andrei ; Teodorescu, Florina ; Varga, Richard A. ; Vanthuyne, Nicolas ; Roussel, Christian and Berg, Ulf LU (2011) In Journal of Molecular Structure 989(1-3). p.20-30
Abstract
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... (More)
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. (Less)
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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
X-ray analyses, Conglomerate, CH/pi interactions, DNMR, Hindered, rotation barriers, DFT calculations
in
Journal of Molecular Structure
volume
989
issue
1-3
pages
20 - 30
publisher
Elsevier
external identifiers
  • wos:000288832800003
  • scopus:79952185766
ISSN
0022-2860
DOI
10.1016/j.molstruc.2010.12.028
language
English
LU publication?
yes
additional info
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)
id
6b046c55-4306-4f56-958d-95ed1c8e65cf (old id 1925819)
date added to LUP
2016-04-01 13:27:32
date last changed
2020-01-12 12:23:47
@article{6b046c55-4306-4f56-958d-95ed1c8e65cf,
  abstract     = {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.},
  author       = {Uncuta, Cornelia and Bartha, Emeric and Gherase, Dragos and Loas, Ioan Andrei and Teodorescu, Florina and Varga, Richard A. and Vanthuyne, Nicolas and Roussel, Christian and Berg, Ulf},
  issn         = {0022-2860},
  language     = {eng},
  number       = {1-3},
  pages        = {20--30},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Structure},
  title        = {Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution},
  url          = {http://dx.doi.org/10.1016/j.molstruc.2010.12.028},
  doi          = {10.1016/j.molstruc.2010.12.028},
  volume       = {989},
  year         = {2011},
}