TUD Organische ChemieImmelGraphicsGalleryCrown AcetalsView or Print this frame onlyView or Print (this frame only)

Top of Page Crown Acetals
Comparison of the cyclodextrin derived crown acetals with 30-crown-12, 35-crown-14, and 40-crown-16 skeletal backbones (all X-ray crystal structures).

Crown Acetals cyclo[-CH(CH2OAc)-CH(CH2OAc)-O-CH(CH2OAc)-O-]n with n = 6-8

30-Crown-12 Hexaacetal
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hir1 hir2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 001 010 100
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cpk1 cpk2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 rib2 rib3
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mod1 mod2 mod3 rib6 riba6 crown crown1 crown2
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prt1 prt2 prt3 prta prtb prtc prtab prtbb prtbc
35-Crown-14 Heptaacetal
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hir1 hir2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 001 010 100
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cpk1 cpk2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 rib2 rib3
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mod1 mod2 mod3 rib7 riba7 crown
40-Crown-14 Octaacetal
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001a 001b 001c 001d 010a 010b 010c 010d 100a 100b 100c 100d
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hir1 hir2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 001 010 100
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cpk1 cpk2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 rib2 rib3
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30-Crown-12 Hexaacetal, 35-Crown-14 Heptaacetal, and 40-Crown-14 Octaacetal
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riba1 riba2 riba3 riba4 ribb1 ribb2b ribb2 ribb3 ribb4
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ribc1 ribc2 ribc3 ribc4 ribd1 ribd2 ribd3b ribd3 ribd4
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For details see:

Molecular Modeling of Saccharides, Part XXVII. Synthesis and Molecular Geometry of an Achiral 30-Crown-12 Polyacetal from α-Cyclodextrin. S. Immel, T. Nakagawa, H. J. Lindner, and F. W. Lichtenthaler, Chem. Eur. J. 2000, 6, 3366-3371.
Abstract / Fulltext PDF

Molecular Modeling of Saccharides, Part XXIX. Hydroxymethyl-substituted crown acetals with 35-C-14 and 40-C-16 skeletal backbones: Synthesis and molecular geometries. S. Immel, F. W. Lichtenthaler, H. J. Lindner, and T. Nakagawa, Tetrahedron: Asymmetry 2001, 12, 2767-2774.
Abstract / Fulltext PDF
Top of Page Crown Acetals
Solid-state structure of a crown acetal with 30-crown-12 skeletal backbone (X-ray crystal structure).

Crown Acetals cyclo[-CH(CH2OH)-CH(CH2OH)-O-CH(CH2OH)-O-]n with n = 6

30-Crown-12 Hexaacetal
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001a 001b 001c 001d 010a 010b 010c 010d 100a 100b 100c 100d
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hir1 hir2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 001 010 100
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cpk1 cpk2 ell1 ell2 bal1 bal2 hyd1 hyd2 rib1 rib2 rib3
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© Copyright PD Dr. S. Immel

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