Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution
(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:
https://lup.lub.lu.se/record/1925819
- author
- Uncuta, Cornelia ; Bartha, Emeric ; Gherase, Dragos ; Loas, Ioan Andrei ; Teodorescu, Florina ; Varga, Richard A. ; Vanthuyne, Nicolas ; Roussel, Christian and Berg, Ulf LU
- organization
- publishing date
- 2011
- 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
- 2022-01-27 19:19:43
@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}},
keywords = {{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}},
doi = {{10.1016/j.molstruc.2010.12.028}},
volume = {{989}},
year = {{2011}},
}