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Interplay Between Conformation and Hydrogen Bond Pattern: Crystal Structure of N-(2,2-dichloroacetyl)-N',N"-dipropylphosphoric Triamide and a Database Survey

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Abstract

The interplay between conformation and hydrogen bond pattern was studied in 211 (C(O)NH)(N)2P(O)-based phosphoric triamides retrieved from the Cambridge Structural Database (CSD) and one new molecular structure, (CHCl2C(O)NH)(CH3CH2CH2NH)2P(O). The O═C–N–P and C–N–P═O torsion angles were extracted for the conformational study of the C(O)NP(O) segment, and the conformations of ±sp±ap, ±sp±sc and ±ap±sp were found (sp = synperiplanar, ap = antiperiplanar, sc = synclinal). The conformations of hydrogen bond donor group(s) with respect to the acceptor group(s) were also considered. The investigated structures belong to three classes of (RC(O)NH)(R1R2N)2P(O) (R1 and R2 ≠ H), (RC(O)NH)(R1NH)2P(O) (R1 ≠ H) and heterocyclic (RC(O)NH)P(O)[NR1]2R2 phosphoric triamides (R1 = H or ≠ H, R2 = a hydrocarbon fragment), and the hydrogen bond patterns include dimer, tetramer, chain, tape, ladder, two-dimensional assembly and three-dimensional architecture. In the new structure, the conformation of the C(O)NP(O) fragment is –sp+ap, and molecules are assembled in a tape arrangement (parallel to the [110] axis) through NCP–H···O═P and NP–H···O═C hydrogen bonds (NCP is the nitrogen atom of the C(O)NHP(O) fragment and NP is the other N atom bonded to phosphorus).

Graphical Abstract

The interplay between conformation and hydrogen bond pattern was studied in 211 (C(O)NH)(N)2P(O)-based phosphoric triamides retrieved from the Cambridge Structural Database (CSD) and one new structure, (CHCl2C(O)NH)(CH3CH2CH2NH)2P(O).

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Data Availability

The datasets generated and analysed during the current study are available from the corresponding author on request.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    Narjess Peyman, Mehrdad Pourayoubi & Ehteram Mohammadi Gooshki

  2. Department of Chemistry, Masaryk University, Kotlarska 2, Brno, 61137, Czech Republic

    Marek Nečas

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  1. Narjess Peyman
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  2. Mehrdad Pourayoubi
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  3. Ehteram Mohammadi Gooshki
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  4. Marek Nečas
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The authors NP, MP, EMG and MN contributed equally to the current manuscript. All authors read and approved the final manuscript.

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Correspondence to Mehrdad Pourayoubi.

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Peyman, N., Pourayoubi, M., Mohammadi Gooshki, E. et al. Interplay Between Conformation and Hydrogen Bond Pattern: Crystal Structure of N-(2,2-dichloroacetyl)-N',N"-dipropylphosphoric Triamide and a Database Survey. J Chem Crystallogr (2024). https://doi.org/10.1007/s10870-024-01015-4

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