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Some new compounds with P(E)NHC(O) (E = lone pair, O, S) linkage: synthesis, spectroscopic, crystal structures, theoretical studies, and antimicrobial evaluation

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Abstract

New phosphinoamides, chalcogenides, and amidophosphates were synthesized and characterized by 1H, 13C, 31P NMR, IR spectroscopy, and elemental analysis. The 13C NMR spectra of two phosphinoamides exhibit obvious differences between their 1 J(P,C) coupling constants (128.3 Hz in one compound vs. 439.2 Hz in another compound). Natural bond orbital analysis was performed to clarify the electronic behavior of the title molecules. The crystal structures of three derivatives were determined by X-ray crystallography. The structure of N-(Diphenylphosphino)-2-pyrazinecarboxamide contains two symmetry-independent forms of the molecule with equal occupancy in the lattice. Density functional theory calculations indicate that two conformers of this compound are identical from an energy point of view. Strong intermolecular N–H···O(P) hydrogen bonds lead to a centrosymmetric dimer in Diphenyl N-(2-pyrazinylcarbonyl)phosphoramidate, whereas N–H···(O)C and N–H···N hydrogen bonds in N-(Diphenylphosphino)-2-pyrazinecarboxamide and N-(Diphenylphosphinothioyl)-2-pyrazinecarboxamide sulfide, respectively, form a one-dimensional polymeric chain in their structures. The in vitro antimicrobial activity of the amidophosphates was evaluated against various microbial strains of Gram positive and Gram negative bacteria and fungi.

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Acknowledgments

The financial support of this work by the Research Council of Tarbiat Modares University is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Khodayar Gholivand

  2. Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran

    Niloufar Dorosti

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  1. Khodayar Gholivand
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  2. Niloufar Dorosti
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Correspondence to Khodayar Gholivand.

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Gholivand, K., Dorosti, N. Some new compounds with P(E)NHC(O) (E = lone pair, O, S) linkage: synthesis, spectroscopic, crystal structures, theoretical studies, and antimicrobial evaluation. Monatsh Chem 144, 1417–1425 (2013). https://doi.org/10.1007/s00706-013-0960-4

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  • DOI: https://doi.org/10.1007/s00706-013-0960-4

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