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Di- and triindolylmethanes: molecular structures and spectroscopic characterization of potentially bidentate and tridentate ligands

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Abstract

4-Bromophenyldi(3-methylindol-2-yl)methane (2) and 2-methoxyphenyldi(3-methylindol-2-yl)methane (3) were prepared by sulfuric-acid-catalyzed reactions of 3-methylindole with 4-bromobenzaldehyde and o-anisaldehyde, respectively. Di(3-methylindol-2-yl)phenylmethane (1) and tri(3-methylindol-2-yl)methane (4) were similarly prepared as described previously. Spectroscopic data (1H, 13C NMR) and the X-ray crystal structures for 1 ⋅C2H5OH and 2–4 are reported. The molecular structure of 1 ⋅C2H5OH shows hydrogen bonding of both indolyl NH protons to the oxygen of an ethanol molecule. Crystal data for 1 ⋅C2H5OH: Orthorhombic, Pca21, a = 23.9782(17) Å, b = 8.4437(7) Å, c = 11.3029(9) Å, V = 2288.4(3) Å3, R 1 = 0.0597. Crystal data for 2: Orthorhombic, P212121, a = 8.911(3) Å, b = 9.584(4) Å, c = 24.040(11) Å, V = 2053.0(14) Å3, R 1 = 0.0454. Crystal data for 3: Monoclinic, P21/c, a = 9.737(2) Å, b = 25.035(6) Å, c = 9.359(2) Å, β = 114.853(4)○, V = 2070.2(8) Å3, R 1 = 0.0511. Crystal data for 4: Trigonal, R3, a = 14.2214(10) Å, c = 9.6190(10) Å, V = 1684.8(2) Å3, R 1 = 0.0425.

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Authors and Affiliations

  1. Department of Chemistry, University of Toledo, Toledo, Ohio, 43606-3390

    Mark R. Mason, Thomas S. Barnard, Mawuto F. Segla, Baohan Xie & Kristin Kirschbaum

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  1. Mark R. Mason
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  2. Thomas S. Barnard
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  3. Mawuto F. Segla
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  4. Baohan Xie
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  5. Kristin Kirschbaum
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Correspondence to Mark R. Mason.

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Mason, M.R., Barnard, T.S., Segla, M.F. et al. Di- and triindolylmethanes: molecular structures and spectroscopic characterization of potentially bidentate and tridentate ligands. Journal of Chemical Crystallography 33, 531–540 (2003). https://doi.org/10.1023/A:1024234618248

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