About: Synthesis and Conformational Properties of Partially Alkylated Methylene-Bridged Resorc[4]arenes - Study of the %22Flip-Flop%22 Inversion     Goto   Sponge   NotDistinct   Permalink

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  • The deprotection of resorc[4]arene octaisopropyl ether 5 by boron trichloride in dichlormethane has been found to give a parent resorc[4]arene, 1, as well as a mixture of partially alkylated derivates, 6, 7, 8 and 9, the ratio of which depended on the conditions used. The conformational behaviour of the prepared alkyl ethers was studied with temperature-dependent 1H NMR spectroscopy and quantum chemical calculations.It was found that the compounds 6, 7 and 8 interconvert between two possible identical crown conformations (flip-flop inversion). The activation free energy deltaG values for this process, obtaining by NMR, strongly depends on the number of hydroxy groups in the molecule; an increase in their number generally increases the values of deltaG.
  • The deprotection of resorc[4]arene octaisopropyl ether 5 by boron trichloride in dichlormethane has been found to give a parent resorc[4]arene, 1, as well as a mixture of partially alkylated derivates, 6, 7, 8 and 9, the ratio of which depended on the conditions used. The conformational behaviour of the prepared alkyl ethers was studied with temperature-dependent 1H NMR spectroscopy and quantum chemical calculations.It was found that the compounds 6, 7 and 8 interconvert between two possible identical crown conformations (flip-flop inversion). The activation free energy deltaG values for this process, obtaining by NMR, strongly depends on the number of hydroxy groups in the molecule; an increase in their number generally increases the values of deltaG. (en)
Title
  • Synthesis and Conformational Properties of Partially Alkylated Methylene-Bridged Resorc[4]arenes - Study of the %22Flip-Flop%22 Inversion
  • Synthesis and Conformational Properties of Partially Alkylated Methylene-Bridged Resorc[4]arenes - Study of the %22Flip-Flop%22 Inversion (en)
skos:prefLabel
  • Synthesis and Conformational Properties of Partially Alkylated Methylene-Bridged Resorc[4]arenes - Study of the %22Flip-Flop%22 Inversion
  • Synthesis and Conformational Properties of Partially Alkylated Methylene-Bridged Resorc[4]arenes - Study of the %22Flip-Flop%22 Inversion (en)
skos:notation
  • RIV/61989592:15310/06:00009828!RIV10-MSM-15310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • S, Z(MSM6046137305)
http://linked.open...iv/cisloPeriodika
  • 19
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 502778
http://linked.open...ai/riv/idVysledku
  • RIV/61989592:15310/06:00009828
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • conformation analysis; density functional theory; partially alkylated resorc[4]arene; transition state (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [77F881560ED5]
http://linked.open...i/riv/nazevZdroje
  • European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 2006
http://linked.open...iv/tvurceVysledku
  • Dvořáková, Hana
  • Čajan, Michal
  • Štursa, Jan
  • Moravcová, Jitka
http://linked.open...n/vavai/riv/zamer
issn
  • 1434-193X
number of pages
http://localhost/t...ganizacniJednotka
  • 15310
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