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NH⋯O and NH⋯N Hydrogen Bonded Networks in Imidazole-Based Phosphane Oxides: Structures of Tris(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide, Bis(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide and Diphenyl-2-Isopropylimidazol-4(5)-yl Phosphane Oxide

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Abstract

The three title compounds show extensive hydrogen bonding networks in the solid state. The structure of diphenyl-2-isopropylimidazol-4(5)yl phosphane oxide (3) is dominated by N–H⋯OP hydrogen bonds, whereas in bis(2-isopropylimidazol-4(5)-yl)phenyl- (2) and tris(2-isopropylimidazol-4(5)yl)phosphane oxide (1) both, N–H⋯N and N–H⋯OP hydrogen bonds determine the solid-state structures. Compound 1 crystallises in the monoclinic space group Cc with cell parameters a = 19.5447(6) Å, b = 10.45764(16) Å, c = 10.8549(3) Å and β = 121.418(4)°; 2 in the orthorhombic space group Pna21, with a = 11.5997(3) Å, b = 9.5836(2) Å, c = 16.1860(4) Å and 3 in the orthorhombic space group Pca21, with a = 10.8430(2) Å, b = 10.9277(2) Å and c = 27.7088(6) Å.

Graphical Abstract

Phosphane oxide compounds with isopropylimidazol-4(5)yl substituents show extensive hydrogen bonding networks in the solid state. The structure of diphenyl-2-isopropylimidazol-4(5)yl phosphane oxide is dominated by N–H⋯OP hydrogen bonds, whereas in bis(2-isopropylimidazol-4(5)-yl)phenyl- and tris(2-isopropylimidazol-4(5)yl)phosphane oxide both, N–H⋯N and N–H⋯OP hydrogen bonds determine the solid-state structures.

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Authors and Affiliations

  1. Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225, Düsseldorf, Germany

    Peter C. Kunz & Wilhelm Huber

  2. Anorganisch-Chemisches Institut, Universität Zürich-Irchel, Winterthurerstr. 190, 8057, Zürich, Switzerland

    Bernhard Spingler

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  1. Peter C. Kunz
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  2. Wilhelm Huber
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  3. Bernhard Spingler
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Correspondence to Peter C. Kunz.

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Kunz, P.C., Huber, W. & Spingler, B. NH⋯O and NH⋯N Hydrogen Bonded Networks in Imidazole-Based Phosphane Oxides: Structures of Tris(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide, Bis(2-Isopropylimidazol-4(5)-yl)Phosphane Oxide and Diphenyl-2-Isopropylimidazol-4(5)-yl Phosphane Oxide. J Chem Crystallogr 41, 105–110 (2011). https://doi.org/10.1007/s10870-010-9845-0

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