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The synergistic cooperation of NH⋯O and CH⋯O hydrogen bonds in the structures of three new phosphoric triamides

  • Saneei, Anahid Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
  • Pourayoubi, Mehrdad Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
  • Jasinski, Jerry P. Department of Chemistry, Keene State College, Keene, NH, USA
  • Jenny, Titus A. Department of Chemistry, University of Fribourg, Switzerland
  • Crochet, Aurélien Fribourg Centre for Nanomaterial’s, FriMat, University of Fribourg, Switzerland
  • Fromm, Katharina M. Fribourg Centre for Nanomaterial’s, FriMat, University of Fribourg, Switzerland
  • Keeley, Amanda C. Department of Chemistry, Keene State College, Keene, NH, USA
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    27.11.2017
Published in:
  • Phosphorus, Sulfur, and Silicon and the Related Elements. - 2017
English The supramolecular assemblies of three new phosphoric triamides, {(C6H5CH2)(CH3)N}2(4-CH3-C6H4C(O)NH)P(O) (1), {(C6H11)(CH3)N}2(4-CH3-C6H4C(O)NH)P(O) (2) and {(C2H5)2N}2(4-CH3-C6H4C(O)NH)P(O) (3) were studied by single crystal X-ray diffraction as well as by Hirshfeld surface analysis. It was found that a synergistic cooperation of NH⋯O and CH⋯O hydrogen bonds occurs in all three structures, but forming unique supramolecular architectures individually. Along with the presence of centrosymmetric dimers in 1, 2 and 3, based on a classical NH⋯O hydrogen bond, the presence of weak CH⋯O interactions play an additional and vital role in crystal architecture and construction of the final assemblies, collectively identified as a centrosymmetric dimer (0D), a 1-D array and a 3-D network, respectively. These differences in superstructures are related to the effect of aromatic, bulk and flexible groups used in the molecules designed, with a similar C(O)NHP(O) backbone. The NH⋯O contacts in 1, 2 and 3 are of the “resonance-assisted hydrogen bond” types and also the anti-cooperativity effect can be considered in the multi-acceptor sites P═O in 1 and 2 and C═O in 3. All three compounds were further studied by 1D NMR experiments, 2D NMR techniques (HMQC and HMBC (H–C correlation)), high resolution ESI–MS, EI–MS spectrometry and IR spectroscopy methods.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/306950
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