TY - JOUR
T1 - Improved synthesis and conformational analysis of an A,D-1,10-phenanthroline-bridged calix[6]arene
AU - Eggert, J.P.W.
AU - Harrowfield, J.M.
AU - Luning, U.
AU - Skelton, Brian
AU - White, Allan
AU - Loffler, F.
AU - Konrad, S.
PY - 2005
Y1 - 2005
N2 - The synthesis of the A,D-1,10-phenanthroline-bridged calix[6]arene 3 is improved by applying a new strategy for the synthesis of the important intermediate 2,9-bis(bromomethyl)-1,10-phenanthroline (2) and variation of the bridging conditions. Crystals were obtained from two different solvent systems. Two structures were determined by X-ray studies. Both analyses reveal a rare conformation for A,D-bridged ca-lix[6]arenes (uduuuu). Calculations with different methods were performed for this and other relevant conformers, and revealed various local minima. The uduuuu conformation also explains the molecular asymmetry evident in low-temperature NMR spectra of metal complexes of 3. (c) Wiley-VCH Verlag GmbH T Co. KGaA, 69451 Weinheim, Germany, 2005).
AB - The synthesis of the A,D-1,10-phenanthroline-bridged calix[6]arene 3 is improved by applying a new strategy for the synthesis of the important intermediate 2,9-bis(bromomethyl)-1,10-phenanthroline (2) and variation of the bridging conditions. Crystals were obtained from two different solvent systems. Two structures were determined by X-ray studies. Both analyses reveal a rare conformation for A,D-bridged ca-lix[6]arenes (uduuuu). Calculations with different methods were performed for this and other relevant conformers, and revealed various local minima. The uduuuu conformation also explains the molecular asymmetry evident in low-temperature NMR spectra of metal complexes of 3. (c) Wiley-VCH Verlag GmbH T Co. KGaA, 69451 Weinheim, Germany, 2005).
U2 - 10.1002/ejoc.200400684
DO - 10.1002/ejoc.200400684
M3 - Article
VL - 2005
SP - 1348
EP - 1353
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1099-0690
ER -