Molecular and crystal structures of N-(n-heptyl)- and N-(n-decyl)-d-gluconamide

Anke Müller-Fahrnow*, Rolf Hilgenfeld, Holger Hesse, Wolfram Saenger, Beate Pfannemüller

*Corresponding author for this work
38 Citations (Scopus)


The crystal structures are described of N-(n-heptyl)-d-gluconamide (1) [space group P1, a = 5.183(7), b = 16.18(1), c = 4.803(5) Å, α = 94.2(1)°, β = 96.1(1)°, γ = 99.0(1)°] and of N-(n-decyl)-d-gluconamide (2) [space group P21, a = 5.255(2), b = 35.97(1), c = 4.807(2) Å, β = 94.81(3)°], and compared with that of N-(n-octyl)-d-gluconamide (3). In contrast to other amphiphilic molecules which form bilayers and crystallise in the tail-to-tail mode, the N-(n-alkyl)-d-gluconamides form monolayers and crystallise in sheet-like head-to-tail arrangements stabilised by intra- and inter-molecular NH ··· O and OH ··· O hydrogen bonds. Compounds (2 and 3) with an even number of alkyl carbon atoms crystallise in space group P21 and those (1) with odd numbers in P1. This situation is correlated with a change in torsion angles around the first CC bond in the alkyl chain and the packing is such that the head CH2OH group interacts virtually identically with the tail group CH2CH3 in each crystal structure. This specific interaction might explain why these molecules form gels in aqueous solution.

Original languageEnglish
JournalCarbohydrate Research
Issue number2
Pages (from-to)165-174
Number of pages10
Publication statusPublished - 15.05.1988

Research Areas and Centers

  • Academic Focus: Center for Infection and Inflammation Research (ZIEL)


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