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Sodium cation complexation in a macrocycle containing thymines as sidearm donor groups

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Abstract

Previous studies of macrocycles having alkyl sidearms terminated in adenine or thymine have been focused on intermolecular association. Electrospray mass spectrometric analyses suggested that sodium complexation could be a major alternative process in the presence of the appropriate cation. Sodium cation complexation by N,N′-bis(3-(1-thyminyl)propyl)-4,13-diaza-18-crown-6 has been confirmed by X-ray crystallographic analysis. A sodium cation is bound in the center of the macroring. The four ether oxygens and two thyminyl carbonyl donors have the shortest contacts with the two, macroring nitrogen atoms being somewhat more remote. Neither the iodide counterion nor an acetone of solvation appears to interact with the sodium cation. Crystal Data: Triclinic, \(P_{\bar 1} \) , a = 11.9371(12), b = 12.1588(13), c = 13.7885(14) Å, α = 78.083(2)°, β = 83.213(2)°, γ = 78.997(2)°, and Dcalc = 1.392 g cm−3, Z = 2.

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Authors and Affiliations

  1. Bioorganic Chemistry Program & Dept. of Molecular Biology & Pharmacology, Washington University School of Medicine, 660 S. Euclid Ave., Campus Box 8103, St. Louis, Missouri, 63110

    Stephen L. De Wall, Otto F. Schall & George W. Gokel

  2. Dept. of Chemistry, University of Missouri, 601 S. College Ave., Columbia, Missouri, 65211

    Leonard J. xbour

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  1. Stephen L. De Wall
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  3. Otto F. Schall
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  4. George W. Gokel
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Wall, S.L.D., xbour, L.J., Schall, O.F. et al. Sodium cation complexation in a macrocycle containing thymines as sidearm donor groups. Journal of Chemical Crystallography 30, 227–231 (2000). https://doi.org/10.1023/A:1009534904760

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