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Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation

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Abstract

Different orientations of P(O) versus C(O) in P(O)NHC(O) skeleton have been discussed in two new phosphorus(V)-nitrogen compounds with formula XP(O)Y and XP(O)Z2 where X = NHC(O)C6H4(4-F) and Y = NHCH2C(CH3)2CH2NH (1), Z = NHC6H4(4-CH3) (2). Compound 1 is the first example of an aliphatic diazaphosphorinane with a gauche orientation which has been studied by X-ray crystallography; the P=O bond is in the equatorial position of the ring. Both compounds show n J(F,C) and m J(F,H) coupling constants (n = 1, 2, 3 and 4; m = 3 and 4) and 3 J(P,C) > 2 J(P,C). Quantum chemical calculations were performed with HF and Density Functional Theory (DFT) methods using 6−31+G(d,p) basis set. A tentative assignment of the observed vibrational bands for these molecules is discussed. Compound 1 shows a deshielded C atom of the carbonyl moiety (in 13C NMR spectrum) relative to that of 2, which is supported by IR spectroscopy in which the considerably lower C=O frequency is observed for 1. Comparing the X-ray crystallography and IR spectra of 1 and 2 shows that the acyclic compound 2, containing P=O and C=O bonds in an anti position, are involving in a stronger N–H···O=P hydrogen bond in crystal network. This leads to a weaker P=O and NC(O)NHP(O)–H bonds and stronger N···O interaction. The Namide–H is involved in an intramolecular N–H···O hydrogen bond.

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Acknowledgments

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged. The authors wish to thank Bruker AXS, Inc. (Madison, WI) for the use of one of their SMART X2S benchtop instruments.

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Authors and Affiliations

  1. Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran

    Atekeh Tarahhomi & Mehrdad Pourayoubi

  2. Department of Chemistry, University of California, San Diego, 9500 Gilman, Drive, La Jolla, CA, 92093, USA

    Arnold L. Rheingold & James A. Golen

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  1. Atekeh Tarahhomi
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  2. Mehrdad Pourayoubi
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Correspondence to Mehrdad Pourayoubi.

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Tarahhomi, A., Pourayoubi, M., Rheingold, A.L. et al. Different orientations of C=O versus P=O in P(O)NHC(O) skeleton: the first study on an aliphatic diazaphosphorinane with a gauche orientation. Struct Chem 22, 201–210 (2011). https://doi.org/10.1007/s11224-010-9682-y

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