Add time:08/27/2019         Source:sciencedirect.com

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 NH ··· O and OH ··· 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 CC 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.

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