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Issue 10, 2011
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Design, synthesis and noncentrosymmetric solid state organization of three novel pyridylphosphonic acids

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Abstract

Three pyridylphosphonic acids, 3-pyridylphosphonic acid 1, 5-(dihydroxyphosphoryl)nicotinic acid 2, and 3,5-pyridinediyldiphosphonic acid 3, were synthesized and structurally investigated by solid state FT-IR and single crystal X-ray diffraction methods. All compounds appear in zwitterionic forms in the solid state with a proton transferred from the phosphonic group toward the pyridine N-atom. Strong hydrogen-bond interactions O–H⋯O and N–H⋯O organize the molecules of the compounds into polar three-dimensional networks. The crystal structures are additionally stabilized via weaker C–H⋯O hydrogen bonds and π⋯π or C[double bond, length as m-dash]O⋯π interactions. Powder second harmonic generation and solution NMR spectra were measured as well. The NMR spectra revealed that the double bonds of the functional groups (P[double bond, length as m-dash]O and C[double bond, length as m-dash]O), although differently oriented versus the Npy atom, are coplanar with the aromatic rings in all stable, low energy conformers of compounds 1–3 in solution. In crystals, however, the P[double bond, length as m-dash]O bonds are tilted toward the ring by 10.77(7)° in 1, 70.42(8)° in 2 and by 43.97(7)° and 6.56(8)° in 3. All three compounds exhibit moderate powder SHG efficiencies compared to that of urea.

Graphical abstract: Design, synthesis and noncentrosymmetric solid state organization of three novel pyridylphosphonic acids

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Publication details

The article was received on 27 Jan 2011, accepted on 24 Feb 2011 and first published on 15 Mar 2011


Article type: Paper
DOI: 10.1039/C1CE05140G
Citation: CrystEngComm, 2011,13, 3474-3484
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    Design, synthesis and noncentrosymmetric solid state organization of three novel pyridylphosphonic acids

    J. Zon, V. Videnova-Adrabinska, J. Janczak, M. Wilk, A. Samoc, R. Gancarz and M. Samoc, CrystEngComm, 2011, 13, 3474
    DOI: 10.1039/C1CE05140G

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