Advanced

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)
Please use this url to cite or link to this publication:
author
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
id
6b046c55-4306-4f56-958d-95ed1c8e65cf (old id 1925819)
date added to LUP
2011-05-11 08:22:45
date last changed
2017-01-01 05:41:03
@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},
  keyword      = {X-ray analyses,Conglomerate,CH/pi interactions,DNMR,Hindered,rotation barriers,DFT calculations},
  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},
  volume       = {989},
  year         = {2011},
}