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Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose

Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose
Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose
A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P2(1) space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P2(1) space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R-3(3) (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P2(1)2(1)2(1) space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P2(1) space group and featured the primary amide groups forming R-2(3)(8) motifs generating a 2(1) ladder.
glucose, cellobiose, primary amides, crystal engineering
0008-6215
29-39
Moynihan, Humphrey A.
4eab6271-11cc-451e-abbf-09b030ee0f2e
Hayes, John A.
df09dc8d-39ca-4a73-a3e6-ed00db6a7256
Eccles, Kevin S.
8e77a90b-b39b-49d8-ae48-42f8573fb242
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lawrence, Simon E.
9f9d8451-35de-4ee7-8c47-ed6e84748b56
Moynihan, Humphrey A.
4eab6271-11cc-451e-abbf-09b030ee0f2e
Hayes, John A.
df09dc8d-39ca-4a73-a3e6-ed00db6a7256
Eccles, Kevin S.
8e77a90b-b39b-49d8-ae48-42f8573fb242
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lawrence, Simon E.
9f9d8451-35de-4ee7-8c47-ed6e84748b56

Moynihan, Humphrey A., Hayes, John A., Eccles, Kevin S., Coles, Simon J. and Lawrence, Simon E. (2013) Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose. Carbohydrate Research, 374, 29-39. (doi:10.1016/j.carres.2013.03.024).

Record type: Article

Abstract

A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P2(1) space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P2(1) space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R-3(3) (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P2(1)2(1)2(1) space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P2(1) space group and featured the primary amide groups forming R-2(3)(8) motifs generating a 2(1) ladder.

Full text not available from this repository.

More information

e-pub ahead of print date: 2 April 2013
Published date: 7 June 2013
Keywords: glucose, cellobiose, primary amides, crystal engineering
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 362489
URI: http://eprints.soton.ac.uk/id/eprint/362489
ISSN: 0008-6215
PURE UUID: cabb24b0-f021-4b6b-9654-63b307d6eaa6
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 25 Feb 2014 13:57
Last modified: 13 Jul 2021 01:37

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