Co-crystallised alpha- and beta-Anomers of 2,3,4,6-Tetra-acetyl-D-glucopyranose, in which the alpha- and beta-Anomers are Randomly Distributed in the Hydrogen-bonded Chains of Molecules

Thomas C. Baddeley, William T. A. Harrison, R. Alan Howie, Janet M. S. Skakle, James Lewis Wardell

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1 Citation (Scopus)

Abstract

A co-crystallised sample of alpha- and beta-2,3,4, 6-tetra-O-acetyl-D-glucopyranose [alpha:beta = 1: 2.86(8)], (alpha, beta-1), has been isolated from a solution of 2,3,4,6-tetra-O-acetyl-D- glucopyranose in moist ethyl acetate/diethyl ether. In contrast, pure b-2,3,4,6-tetra-O-acetyl-D- glucopyranose, (beta-1) was isolated on crystallisation from diethyl ethyl/petroleum ether. Species (alpha,beta- 1) is a solid solution in which approximately one in four of the molecules in the b- form is randomly substituted by a molecule of the a- anomer. The hydrogen bonded zig-zag chain connectivity of the pure b- anomer is maintained in the solid solution along the b direction. Since the parent D-glucopyranose compounds differ in their molecular packing and, therefore in structure, the solid solution phenonmenon in the case of their tetraacetyl derivatives is unexpected. Compound (beta- 1) and the (alpha, beta-1) solid solution crystallize in the orthorhombic space group P2(1)2(1)2(1):a = 7.8612( 4) angstrom, b = 10.2045( 5) angstrom, c = 20.7362( 11) angstrom, and Z = 4 for (alpha- 1) at 120( 2) K; and a = 7.9674(5) A, b = 10.2547( 4) angstrom, c = 21.1565( 10) angstrom, and Z = 4 for ( alpha, beta-1) at 291(2) K.

Original languageEnglish
Pages (from-to)853-858
Number of pages6
JournalJournal of Chemical Crystallography
Volume37
Issue number12
DOIs
Publication statusPublished - Dec 2007

Keywords

  • co-crystallised anomers
  • solid solution
  • glucopyranose derivatives
  • acetals
  • glucose

Cite this

@article{0c44e838672f480e8e11439b9daf5eba,
title = "Co-crystallised alpha- and beta-Anomers of 2,3,4,6-Tetra-acetyl-D-glucopyranose, in which the alpha- and beta-Anomers are Randomly Distributed in the Hydrogen-bonded Chains of Molecules",
abstract = "A co-crystallised sample of alpha- and beta-2,3,4, 6-tetra-O-acetyl-D-glucopyranose [alpha:beta = 1: 2.86(8)], (alpha, beta-1), has been isolated from a solution of 2,3,4,6-tetra-O-acetyl-D- glucopyranose in moist ethyl acetate/diethyl ether. In contrast, pure b-2,3,4,6-tetra-O-acetyl-D- glucopyranose, (beta-1) was isolated on crystallisation from diethyl ethyl/petroleum ether. Species (alpha,beta- 1) is a solid solution in which approximately one in four of the molecules in the b- form is randomly substituted by a molecule of the a- anomer. The hydrogen bonded zig-zag chain connectivity of the pure b- anomer is maintained in the solid solution along the b direction. Since the parent D-glucopyranose compounds differ in their molecular packing and, therefore in structure, the solid solution phenonmenon in the case of their tetraacetyl derivatives is unexpected. Compound (beta- 1) and the (alpha, beta-1) solid solution crystallize in the orthorhombic space group P2(1)2(1)2(1):a = 7.8612( 4) angstrom, b = 10.2045( 5) angstrom, c = 20.7362( 11) angstrom, and Z = 4 for (alpha- 1) at 120( 2) K; and a = 7.9674(5) A, b = 10.2547( 4) angstrom, c = 21.1565( 10) angstrom, and Z = 4 for ( alpha, beta-1) at 291(2) K.",
keywords = "co-crystallised anomers, solid solution, glucopyranose derivatives, acetals, glucose",
author = "Baddeley, {Thomas C.} and Harrison, {William T. A.} and Howie, {R. Alan} and Skakle, {Janet M. S.} and Wardell, {James Lewis}",
year = "2007",
month = "12",
doi = "10.1007/s10870-007-9259-9",
language = "English",
volume = "37",
pages = "853--858",
journal = "Journal of Chemical Crystallography",
issn = "1074-1542",
publisher = "Springer New York",
number = "12",

}

TY - JOUR

T1 - Co-crystallised alpha- and beta-Anomers of 2,3,4,6-Tetra-acetyl-D-glucopyranose, in which the alpha- and beta-Anomers are Randomly Distributed in the Hydrogen-bonded Chains of Molecules

AU - Baddeley, Thomas C.

AU - Harrison, William T. A.

AU - Howie, R. Alan

AU - Skakle, Janet M. S.

AU - Wardell, James Lewis

PY - 2007/12

Y1 - 2007/12

N2 - A co-crystallised sample of alpha- and beta-2,3,4, 6-tetra-O-acetyl-D-glucopyranose [alpha:beta = 1: 2.86(8)], (alpha, beta-1), has been isolated from a solution of 2,3,4,6-tetra-O-acetyl-D- glucopyranose in moist ethyl acetate/diethyl ether. In contrast, pure b-2,3,4,6-tetra-O-acetyl-D- glucopyranose, (beta-1) was isolated on crystallisation from diethyl ethyl/petroleum ether. Species (alpha,beta- 1) is a solid solution in which approximately one in four of the molecules in the b- form is randomly substituted by a molecule of the a- anomer. The hydrogen bonded zig-zag chain connectivity of the pure b- anomer is maintained in the solid solution along the b direction. Since the parent D-glucopyranose compounds differ in their molecular packing and, therefore in structure, the solid solution phenonmenon in the case of their tetraacetyl derivatives is unexpected. Compound (beta- 1) and the (alpha, beta-1) solid solution crystallize in the orthorhombic space group P2(1)2(1)2(1):a = 7.8612( 4) angstrom, b = 10.2045( 5) angstrom, c = 20.7362( 11) angstrom, and Z = 4 for (alpha- 1) at 120( 2) K; and a = 7.9674(5) A, b = 10.2547( 4) angstrom, c = 21.1565( 10) angstrom, and Z = 4 for ( alpha, beta-1) at 291(2) K.

AB - A co-crystallised sample of alpha- and beta-2,3,4, 6-tetra-O-acetyl-D-glucopyranose [alpha:beta = 1: 2.86(8)], (alpha, beta-1), has been isolated from a solution of 2,3,4,6-tetra-O-acetyl-D- glucopyranose in moist ethyl acetate/diethyl ether. In contrast, pure b-2,3,4,6-tetra-O-acetyl-D- glucopyranose, (beta-1) was isolated on crystallisation from diethyl ethyl/petroleum ether. Species (alpha,beta- 1) is a solid solution in which approximately one in four of the molecules in the b- form is randomly substituted by a molecule of the a- anomer. The hydrogen bonded zig-zag chain connectivity of the pure b- anomer is maintained in the solid solution along the b direction. Since the parent D-glucopyranose compounds differ in their molecular packing and, therefore in structure, the solid solution phenonmenon in the case of their tetraacetyl derivatives is unexpected. Compound (beta- 1) and the (alpha, beta-1) solid solution crystallize in the orthorhombic space group P2(1)2(1)2(1):a = 7.8612( 4) angstrom, b = 10.2045( 5) angstrom, c = 20.7362( 11) angstrom, and Z = 4 for (alpha- 1) at 120( 2) K; and a = 7.9674(5) A, b = 10.2547( 4) angstrom, c = 21.1565( 10) angstrom, and Z = 4 for ( alpha, beta-1) at 291(2) K.

KW - co-crystallised anomers

KW - solid solution

KW - glucopyranose derivatives

KW - acetals

KW - glucose

U2 - 10.1007/s10870-007-9259-9

DO - 10.1007/s10870-007-9259-9

M3 - Article

VL - 37

SP - 853

EP - 858

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

SN - 1074-1542

IS - 12

ER -