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Synthesis and self-aggregation of enantiopure and racemic molecular tweezers based on the bicyclo[3.3.1]nonane framework.

Wallentin, Carl-Johan LU ; Wixe, Torbjörn LU ; Wendt, Ola LU ; Bergquist, Karl-Erik LU and Wärnmark, Kenneth LU (2010) In Chemistry - A European Journal 16(13). p.3994-4002
Abstract
A pair of molecular tweezers (syn-4) that consists of quinoline and pyrazine units fused to a bicyclic framework is presented. The tweezers were synthesised both as a racemic mixture (rac-4) and an enantiomerically pure form ((R,R,R,R)-4) starting from either racemic or enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione (3). Homochiral dimers were observed in the solid state for rac-4. The self-association of both rac-4 and (R,R,R,R)-4 was studied in solution. A weak self-association constant in CDCl(3) was estimated by (1)H NMR spectroscopic dilution titration experiments in both cases, following several proton resonances. For this purpose, a general normalisation model for the accurate determination of association constants from... (More)
A pair of molecular tweezers (syn-4) that consists of quinoline and pyrazine units fused to a bicyclic framework is presented. The tweezers were synthesised both as a racemic mixture (rac-4) and an enantiomerically pure form ((R,R,R,R)-4) starting from either racemic or enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione (3). Homochiral dimers were observed in the solid state for rac-4. The self-association of both rac-4 and (R,R,R,R)-4 was studied in solution. A weak self-association constant in CDCl(3) was estimated by (1)H NMR spectroscopic dilution titration experiments in both cases, following several proton resonances. For this purpose, a general normalisation model for the accurate determination of association constants from multiple datasets was developed. In contrast to the solid state, no diastereomeric discrimination was observed for rac-4 in solution. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemistry - A European Journal
volume
16
issue
13
pages
3994 - 4002
publisher
John Wiley & Sons
external identifiers
  • wos:000276735900016
  • pmid:20187041
  • scopus:77950287608
ISSN
1521-3765
DOI
10.1002/chem.200902925
language
English
LU publication?
yes
id
3fe71624-b194-4b7b-8ec4-54d3116e34a0 (old id 1582821)
date added to LUP
2010-04-21 12:03:10
date last changed
2018-05-29 11:25:07
@article{3fe71624-b194-4b7b-8ec4-54d3116e34a0,
  abstract     = {A pair of molecular tweezers (syn-4) that consists of quinoline and pyrazine units fused to a bicyclic framework is presented. The tweezers were synthesised both as a racemic mixture (rac-4) and an enantiomerically pure form ((R,R,R,R)-4) starting from either racemic or enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione (3). Homochiral dimers were observed in the solid state for rac-4. The self-association of both rac-4 and (R,R,R,R)-4 was studied in solution. A weak self-association constant in CDCl(3) was estimated by (1)H NMR spectroscopic dilution titration experiments in both cases, following several proton resonances. For this purpose, a general normalisation model for the accurate determination of association constants from multiple datasets was developed. In contrast to the solid state, no diastereomeric discrimination was observed for rac-4 in solution.},
  author       = {Wallentin, Carl-Johan and Wixe, Torbjörn and Wendt, Ola and Bergquist, Karl-Erik and Wärnmark, Kenneth},
  issn         = {1521-3765},
  language     = {eng},
  number       = {13},
  pages        = {3994--4002},
  publisher    = {John Wiley & Sons},
  series       = {Chemistry - A European Journal},
  title        = {Synthesis and self-aggregation of enantiopure and racemic molecular tweezers based on the bicyclo[3.3.1]nonane framework.},
  url          = {http://dx.doi.org/10.1002/chem.200902925},
  volume       = {16},
  year         = {2010},
}