Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH14535 > Fulltext
RESEARCH FRONT
Contents Vol 68(3)

Zwitterionic CS2 Adducts of Bis(dialkylphosphino)amines: Syntheses, Spectroscopy, and Structures*

Diane A. Dickie A , Raymond P. Ulibarri-Sanchez III B and Richard A. Kemp A B C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131, USA.

B Advanced Materials Laboratory, Sandia National Laboratories, Albuquerque, NM 87106, USA.

C Corresponding author. Email: rakemp@unm.edu

Australian Journal of Chemistry 68(3) 351-356 https://doi.org/10.1071/CH14535
Submitted: 31 August 2014  Accepted: 19 September 2014   Published: 7 November 2014

Abstract

Both bis(diisopropylphosphino)amine and bis(di-t-butylphosphino)amine react with CS2 to give bright red zwitterionic adducts of the form R2P(CS2)NP(R2)H (R = iPr or tBu). The P–H tautomer is the exclusive species present in solution, and there is no evidence of CS2 lability. The tautomeric hydrogen can undergo exchange with deuterium in protic solvents such as CD3OD. The products were characterized by single-crystal X-ray diffraction, IR and multinuclear (1H, 2H, 13C, 31P) NMR spectroscopies.


References

[1]  A. W. Hofmann, Ann. Chem. Suppl. Bd 1861, 1, 1.

[2]  K. Issleib, A. Brack, Z. Anorg. Allg. Chem. 1954, 277, 271.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG2MXjtFKktg%3D%3D&md5=2a6243b8beb475413e4d40b01fd2ec32CAS |

[3]  (a) Y. G. Shtyrlin, N. I. Tyryshkin, G. G. Iskhakova, V. V. Gavrilov, V. D. Kiselev, A. I. Konovalov, Russ. J. Gen. Chem. 1995, 65, 1004. [Zh. Obshch. Khim. 1995, 65, 1101].
      (b) G. G. Iskhakova, V. D. Kiselev, R. van Eldik, A. Zahl, M. S. Shihab, A. I. Konovalov, J. Phys. Org. Chem. 2011, 24, 360.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) T. N. Margulis, D. H. Templeton, J. Am. Chem. Soc. 1961, 83, 995.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXosFWgsw%3D%3D&md5=95b30d4b7d609cb3ed89bfeb16fb0e92CAS |
      (b) T. N. Margulis, D. H. Templeton, J. Chem. Phys. 1962, 36, 2311.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  B. Hoge, C. Thoesen, T. Herrmann, I. Pantenburg, Inorg. Chem. 2002, 41, 2260.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XitlCkur4%3D&md5=89824b4931d8d7af7cef0e12e32483fcCAS | 11952383PubMed |

[6]  R. F. de Souza, D. Thiele, A. L. Monteiro, J. Catal. 2006, 241, 232.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) R. A. Aitken, K. Carcas, L. Hill, T. Massil, S. V. Raut, Tetrahedron 1997, 53, 2261.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXhtFags7c%3D&md5=6149330c299823490fb3ee20ad98fa15CAS |
      (b) R. A. Aitken, N. J. Wilson, Sulfur Rep. 1998, 21, 81.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  A. Galindo, D. Miguel, J. Perez, Coord. Chem. Rev. 1999, 193–195, 643.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  F. H. Allen, Acta. Crystallogr., Sect. B: Struct. Sci. 2002, 58, 380.[CSD version 5.35, May 2014 update].
         | Crossref | GoogleScholarGoogle Scholar |

[10]  K. Tani, J. Onouchi, T. Yamagata, Y. Kataoka, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, 51, 2073.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  (a) S. Stallinger, C. Reitsamer, W. Schuh, H. Kopacka, K. Wurst, P. Peringer, Chem. Commun. 2007, 510.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotFKkug%3D%3D&md5=d8cc2c29e3baed3c728598561324fff8CAS |
      (b) C. Reitsamer, S. Stallinger, W. Schuh, H. Kopacka, K. Wurst, D. Obendorf, P. Peringer, Dalton Trans. 2012, 3503.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) C. A. Stewart, D. A. Dickie, Y. Tang, R. A. Kemp, Inorg. Chim. Acta 2011, 376, 73.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtF2rtb7I&md5=9ac6abcade68820aba6eb07533434a53CAS |
      (b) C. A. Stewart, D. A. Dickie, M. V. Parkes, J. A. Saria, R. A. Kemp, Inorg. Chem. 2010, 49, 11133.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. A. Stewart, D. A. Dickie, B. Moasser, R. A. Kemp, Polyhedron 2012, 32, 14.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. A. Dickie, R. P. Ulibarri-Sanchez, P. J. Jarman, R. A. Kemp, Polyhedron 2013, 58, 92.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) D. A. Dickie, M. V. Parkes, R. A. Kemp, Angew. Chem. Int. Ed. 2008, 47, 9955.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. A. Dickie, E. N. Coker, R. A. Kemp, Inorg. Chem. 2011, 50, 11288.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) R. W. Light, L. D. Hutchins, R. T. Paine, C. F. Campana, Inorg. Chem. 1980, 19, 3597.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXktVKltw%3D%3D&md5=33f98a19d9e49168fc3ca324ac778b4fCAS |
      (b) P. J. Heard, Prog. Inorg. Chem. 2005, 53, 1.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  S. D. Robertson, T. Chivers, Dalton Trans. 2008, 1765.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjsFCmtLo%3D&md5=186d79d8ecdd6ed40b6fb4e325c964e1CAS | 18354775PubMed |

[15]  T. Chivers, D. J. Eisler, J. S. Ritch, H. M. Tuononen, Angew. Chem. Int. Ed. 2005, 44, 4953.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpsFCmsr8%3D&md5=b372a750313b69a1f5e1a6585563b038CAS |

[16]  B. M. Barry, D. A. Dickie, L. J. Murphy, J. Clyburne, R. A. Kemp, Inorg. Chem. 2013, 52, 8312.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFCrtL7O&md5=ddd21a148ef4028ff5af35ef7d30aa56CAS | 23879626PubMed |

[17]  D. S. Kummli, H. M. Frey, S. Leutwyler, J. Chem. Phys. 2006, 124, 144307.
         | Crossref | GoogleScholarGoogle Scholar | 16626196PubMed |

[18]  P. J. W. Elder, T. Chivers, R. Thirumoorthi, Eur. J. Inorg. Chem. 2013, 2867.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXlvFWmsrg%3D&md5=1d8594335e25168bccfa5c162d3aa901CAS |

[19]  J. S. Ritch, T. Chivers, D. J. Eisler, H. M. Tuononen, Chem. – Eur. J. 2007, 13, 4643.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmt12nsbk%3D&md5=cf877c91c693e6818b222f0fd4463675CAS | 17348055PubMed |

[20]  Bruker AXS, APEX2 2007 (Bruker AXS, Inc.: Madison, WI)