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Issue 45, 2017
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Salts of 4-aminobutyric acid and 6-aminohexanoic acid behaving as molecular Velcro

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Abstract

The crystal structures of eight novel carboxyalkylammonium salts, (+H3N(CH2)nCOOH)X, are reported, with n = 4 and X = Cl, Br and I in structures 1, 2 and 3, respectively, and n = 6 and X = Cl, Br·0.5H2O, Cl·0.5H2O, NO3 and ClO4 in structures 4, 5, 6, 7 and 8. The members of this family of compounds were found to display significant structural diversity, and a careful analysis of the structures employing the principles of crystal engineering was done to explain the observed trends and differences, specifically also the interdigitation or non-interdigitation of alkyl chains. It was found that a primary hydrogen bonding network formed between the ammonium groups and halide or oxo-anions, which plays a major structure-directing role. The structures may be likened to molecular Velcro, in which secondary hydrogen bonding interactions involving the carboxylic acid groups act as “hooks” to link primary networks.

Graphical abstract: Salts of 4-aminobutyric acid and 6-aminohexanoic acid behaving as molecular Velcro

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Publication details

The article was received on 04 Sep 2017, accepted on 30 Oct 2017 and first published on 31 Oct 2017


Article type: Paper
DOI: 10.1039/C7CE01597F
Citation: CrystEngComm, 2017,19, 6821-6836
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    Salts of 4-aminobutyric acid and 6-aminohexanoic acid behaving as molecular Velcro

    M. Rademeyer and B. van der Westhuizen, CrystEngComm, 2017, 19, 6821
    DOI: 10.1039/C7CE01597F

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