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Inclusion complexes of selected amines with pillar[5]arenes: experimental and molecular dynamics study

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Abstract

Selected amines were allowed to form inclusion complexes with selected synthesized pillar[5]arenes. Formation of inclusion complexes were confirmed by MALDI–TOF, ESI–MS analyses and 1H NMR spectroscopy. The complexation was supported by molecular dynamics calculations. Various pillar[5]arenes have been synthesized by BF3·OEt2 (Lewis acid) catalyzed cyclization of 1,4-disubstitutedbenzenes with paraformaldehyde. Selected synthesized host macrocycles; DMpillar[5]arene (7), DPpillar[5]arene (8a), DPGpillar[5]arene (8b) were allowed to form inclusion complexes with N-containing guests; hexamethylenediamine (GA), di-n-octyl amine (GB) and diethyl amine (GC). Host–guest complex formation of the selected pillar[5]arenes with the N-containing guests has been confirmed by MALDI–TOF, ESI–MS analyses and 1H NMR spectroscopy. ESI–MS revealed highly intense ion peaks that correspond to [pillar[5]arene@GA+Na]+ for inclusion complexes of pillar[5]arenes with hexamethylenediamine (GA). ESI–MS confirmed formation of inclusion complexes between pillar[5]arenes with di-n-octyl amine (GB) and diethyl amine (GC) as evidenced by intense peaks that corresponds to [pillar[5]arene@GB+H]+ and [pillar[5]arene@GC+H]+, respectively. Performed molecular dynamics (MD) simulations provided supportive results that indicate the formation of stable complexes between the three pillar[5]arene hosts and the guests included in this study. Hydrogen bonding and CH–π interactions were found amongst the factors that contribute significantly to the stability of these complexes.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Sultan Qaboos University, PO Box 36, Al Khoudh 123, Muscat, Sultanate of Oman

    Hamad H. Al Mamari, Iman Al Harrasi, Khulood Al Hadhrami, Yousuf Al Lawati & Fakhreldin O. Suliman

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  1. Hamad H. Al Mamari
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  2. Iman Al Harrasi
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  3. Khulood Al Hadhrami
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  4. Yousuf Al Lawati
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  5. Fakhreldin O. Suliman
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Correspondence to Hamad H. Al Mamari.

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Al Mamari, H.H., Al Harrasi, I., Al Hadhrami, K. et al. Inclusion complexes of selected amines with pillar[5]arenes: experimental and molecular dynamics study. J Incl Phenom Macrocycl Chem 96, 297–306 (2020). https://doi.org/10.1007/s10847-019-00971-1

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