Complexing properties of a bisdianhydro-D-mannitolo-30-crown-10 derivative in the solution and solid states; X-ray crystal structure

Abstract

X-Ray crystallography has revealed that the chiral 30-crown-10 derivative DD-(2) adopts a basketlike conformation when it forms a 1 : 1 : 1 complex with (S)-[PhCHMeNH,]+ Cl0,-and H20 in the solid state; lH n.m.r. spectroscopy suggests that 1 : 1 : 1 complexes of this type between (i) D D -( ~) , RINH,+ cations, and H,O, and (ii) D D -( ~) , RINH,+ cations, and R2NH2 are also stable in solution.

Diastereoselective Self-Assembly of Double- and Triple-Stranded Helicates from a d-Isomannide Derivative

“…d -Isomannide was first described in 1882 by Fauconnier, but its structure was not elucidated until 1946 in asymmetric catalysis, for the self-assembly of [2]catenanes, and the construction of crown ether derivatives for the recognition of ammonium salts; very recently, the photoswitching behavior of a diazobenzene analogue has been investigated . Additionally, 4-pyridyl-substituted ligands have been prepared from d -isomannide and d -isosorbide that form triple-stranded coordination networks of helical shape with HgCl 2 …”

Structure of a chiral monopyrido crown ether: 1,4:1',4':3,6:3',6'-tetraanhydro-5,5'-O-oxydiethylene-2,2'-O-[pyridine-2,6-diylbis(methylene)]-di-D-mannitol

“…'face-to-face' conformation compatible with the creation of a hydrophilic cavity for binding of two guest species simultaneously (Metcalfe, Stoddart, Jones, Crawshaw, Gavuzzo & Williams, 1981). By contrast, we have found more recently in the 1:2 adduct of DD-(2) with BH3NH a that, although the same type of host geometry is adopted, the conformation of one of the polyether chains is subtly modified such that the resulting complexation of the two BH3NH 3 guest molecules is to both sides of the host (ShahriariZavareh, Stoddart, Williams, Allwood & Williams, 1985).…”

“…As part of a research programme directed towards the synthesis of chiral crown ethers incorporating carbohydrate residues (Stoddart, 1979(Stoddart, , 1981Crawshaw, Laidler, Metcalfe, Pettman, Stoddart & Wolstenholme, 1982), 1,4:3,6-dianhydro-D-mannitol ID-(1)I (Montgomery & Wiggins, 1948;Goodwin, Hodge & Weisleder, 1980) has been identified as a readily available and inexpensive synthetic precursor (Metcalfe, Stoddart, Jones, Crawshaw, Quick & Williams, 1981;Metcalfe, Stoddart, Jones, Crawshaw, Gavuzzo & Williams, 1981). This diol D-(1) may be regarded as a 'chiral triethylene glycol unit' (HO-…”

Structure of a chiral bisanisylene crown ether, 1,4:1',4':3,6:3',6'-tetraanhydro-2,2':5,5'-bis-O-[2-methoxy-1,3-phenylenebis(methylene)]di-D-mannitol

“…In order to confer greater rigidity upon receptor molecules such as DD-(1) (Metcalfe, Stoddart, Jones, Crawshaw, Quick & Williams, 1981;Metcalfe, Stoddart, Jones, Crawshaw, Gavuzzo & Williams, 1981) and DD-(2) (Crawshaw, Stoddart & Williams, 1986) containing 1,4:3,6-dianhydro-D-mannitol, it was decided to appeal to 2-substituted-l,3-xylylene units as constitutional building blocks and rigid spacer groups.…”

“…In order to confer greater rigidity upon receptor molecules such as DD- (1) (Metcalfe, Stoddart, Jones, Crawshaw, Quick & Williams, 1981;Metcalfe, Stoddart, Jones, Crawshaw, Gavuzzo & Williams, 1981) and DD-(2) (Crawshaw, Stoddart & Williams, 1986) containing 1,4:3,6-dianhydro-D-mannitol, it was decided to appeal to 2-substituted-l,3-xylylene units as constitutional building blocks and rigid spacer groups. Since the first report (Vfgtle & Weber, 1974) of the use of these units in the synthesis of macrocyclic hosts, they have found wide application (McKervey & Mulholland, 1977;Newcomb, Moore & Cram, 1977;van der Leij, Oosternik, Hall & Reinhoudt, 1981;McKervey & O'Connor, 1982).…”