2365-73-3Relevant academic research and scientific papers
Aromatic triazole foldamers induced by C-H...X (X = F, Cl) intramolecular hydrogen bonding
Shang, Jie,Gallagher, Nolan M.,Bie, Fusheng,Li, Qiaolian,Che, Yanke,Wang, Ying,Jiang, Hua
, p. 5134 - 5144 (2014/06/23)
Aryl-triazole oligomers based on isobutyl 4-fluorobenzoate and isobutyl 4-chlorobenzoate were designed and synthesized. Crystal structure and 1H-1H NOESY experiments demonstrate that the oligomers adopt stable helical conformation, which are induced by C5-H...X-C (X = F, Cl) intramolecular hydrogen bonding between triazole protons and halogen atoms. The stabilities of the folded conformations are confirmed by DFT calculations, which show that each C5-H...F-C planar interaction lowers the energy by ~3 kcal mol-1 on average, and by ~1 kcal mol-1 when C5-H...Cl-C bridges are formed. The hydrogen-bonding networks are disrupted in competitive hydrogen-bonding media such as DMSO, generating the unfolded oligomers.
Self-assembly of vesicles from the stacking of a dipodal F?H-N hydrogen bonded arylamide foldamer
Wang, Lu,Xiao, Ze-Yun,Hou, Jun-Li,Wang, Gui-Tao,Jiang, Xi-Kui,Li, Zhan-Ting
experimental part, p. 10544 - 10551 (2010/02/27)
In this paper, we report the synthesis and self-assembling behavior of an F?H-N hydrogen bonding-induced arylamide-based dipodal foldamer. SEM, AFM, TEM, and XRD studies reveal that this preorganized oligomer stacks to form vesicles in methanol-chloroform
F...H-N hydrogen bonding driven foldamers: Efficient receptors for dialkylammonium ions
Li, Chuang,Ren, Shi-Fang,Hou, Jun-Li,Yi, Hui-Ping,Zhu, Shi-Zheng,Jiang, Xi-Kui,Li, Zhan-Ting
, p. 5725 - 5729 (2007/10/03)
(Graph Presented) Intramolecular F...H-N hydrogen bonds have been utilized for the first time to construct a new series of foldamers from aromatic amides (see picture; R1 = H, Me; R2 = CON(n-C 8H17)2)
A new, efficient glycosylation method for oligosaccharide synthesis under neutral conditions: Preparation and use of new DISAL donors
Petersen,Jensen
, p. 6268 - 6275 (2007/10/03)
Efficient, stereoselective glycosylation methods are required for the synthesis of complex oligosaccharides as tools in glycobiology. All glycosylation methods, which have found wide acceptance, rely on Lewis acid activation of glycosyl donors prior to glycosylation. Here, we present a new and efficient method for glycosylation under neutral or mildly basic conditions. Glycosides of methyl 2-hydroxy-3,5-dinitrobenzoate (DISAL) and its para regioisomer, methyl 4-hydroxy-3,5-dinitrobenzoate, were prepared by nucleophilic aromatic substitution. In a first demonstration of their potential as glycosyl donors, stereospecific glycosylation of methanol was achieved. In the glycosylation of more hindered alcohols, the β-donor proved more reactive, and α-glucosides were predominantly formed. Glycosylation of protected monosaccharides, with free 6-0H or 3-OH, proceeded smoothly in 1-methyl-2-pyrrolidinone (NMP) at 40-60 °C in the absence of Lewis acids and bases in good to excellent yields. Glycosylation of 3-OH gave the α-linked disaccharide only.
