Skip to main content
SpringerLink
Log in

Synthesis and Characterization of Silver(I) Complexes with C-Alkyl Functionalized N,N′-Diphenylamidinates: Tetrameric and Trimeric Structural Motifs

  • Published:
Journal of Cluster Science Aims and scope Submit manuscript

Abstract

N,N′−Diphenylamidines and the silver(I) complexes of their deprotonated anions have been synthesized. Previously uncharacterized tetrameric structural motifs were produced by the inclusion of alkyl substituents at the amidinate carbon. The addition of a 2-methoxy functional group to the phenyl ring resulted in a cationic silver trimer in which hydrogen bonding links silver(I)-bound water molecules to the methoxy substituents. The thermal stabilities of the tetrameric species vary with alkyl chain length. The new complexes are: tetrakis(N,N′-diphenylpropamidinato) tetra silver(I), 1, tetrakis(N,N′-diphenylbutamidinato) tetrasilver(I) 2, tetrakis(N,N′-diphenylpentamidinato) tetra silver(I) 3, (N,N′-diphenyloctamidinato)silver(I) 4, (tetrakis(N,N′-di(4-n-butyl)phenylpropamidinato)tetrasilver(I), 5, bis(N,N′-di(2-methoxy)phenylacetamidinato)diaquatrisilver(I) nitrate 6 and tetrakis(N,N′-di(4-methoxy)phenylacetamidinato) tetrasilver(I), 7. Compounds 1, 5, 6 and 7 were structurally characterized by X-ray methods.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. D. H. Klosterboer, Imaging Processes and Materials, Chapter 9, Neblette, 8th ed.

  2. (a) The United Kingdom Chemical Database Service; D. A. Fletcher, R. F. McMeeking, and D. J. Parkin (1996). J. Chem. Info. Comput. Sci. 36, 746; (b) A. E. Blakeslee and J. L. Hoard (1956). J. Am. Chem. Soc. 78, 3029; (c) P. Coggon and A. T. McPhail (1972). J. Chem. Soc. Chem. Commun. 91; (d) R. G. Griffin, J. D. Ellett, Jr., M. Mehring, J. G. Bullitt, and J. S. Waugh (1972). J. Chem. Phys. 57, 2147; (e) V.-M. Hedrich and H. Hartl (1983). Acta. Cryst. C39, 533; (f ) T. C. W. Mak, W.-H. Yip, C. H. L. Kennard, G. Smith, and E. J. O'Reilly (1988). Aust. J. Chem. 41, 683; (g) G. Smith, D. S Sagatys, C. A. Campbell, D. E. Lynch, and C. H. L. Kennard (1990). Aust. J. Chem. 43, 1707; (h) X.-M. Chen, and T. C. W. Mak (1991). J. Chem. Soc., Dalton Trans. 1219; (i) P.-R. Wei, D.-D. Wu, and T. C. W. Mak (1996). Inorg. Chim. Acta 249, 169; ( j) B. P. Tolochko, S. V. Chernov, S. G. Nikitenko, and D. R. Whitcomb (1998). Nuclear Instruments and Methods in Physics Research, (A) 405, 428.

    Google Scholar 

  3. (a) J. Barker and M. Kilner (1994). Coord. Chem. Rev. 133, 219; (b) I. D. Brown and J. D. Dunitz (1961). Acta. Cryst. 14, 480; (c) J. Beck and J. Stra_ hle (1986). Z. Naturforsch. 41b, 4; (d) E. Hartmann and J. Strähle (1988). Z. Naturforsch. 43b, 818; (e) S. Maier, W. Hiller, J. Strähle, C. Ergezinger, and K. Dehnicke (1988). Z. Naturforsch. 43b, 1628; (f ) F. A. Cotton, X. Feng, M. Matusz, and R. Poli (1988). J. Am. Chem. Soc. 110, 7077; (g) D. Fenske, G. Baum, Zinn, and K. Dehnicke (1990). Z. Naturforsch. 45b, 1273.

    Google Scholar 

  4. (a) T. Ren, C. Lin, P. Amalberti, D. Mdacikenas, J. D. Protasiewicz, J. C. Baum, and T. L. Gibson (1998). Inorg. Chem. Commun. 1, 23; (b) S. J. Archibald, N. W. Alcock, and D. H. Busch, paper submitted.

    Google Scholar 

  5. E. Hartmann and J. Strähle (1989). Z. Naturforsch. 44b, 1.

    Google Scholar 

  6. J. Beck and J. Strähle (1986). Angew. Chem. Int. Ed. 25, 95.

    Google Scholar 

  7. J. E. O'Connor, G. A. Janusonis, and E. R. Corey (1968). J. Chem. Soc., Chem. Commun. 445.

  8. E. Hartmann and J. Strähle (1990). Z. Anorg. Allg. Chem. 583, 31.

    Google Scholar 

  9. P. I. van Vliet, G. van Koten, and K. Vrieze (1979). J. Organomet. Chem. 179, 89.

    Google Scholar 

  10. S. Patai, The Chemistry of Amidines and Imidates (Wiley and Sons, 1975), Vol. 1.

  11. E. C. Taylor and W. A. Erhart (1963). J. Org. Chem. 28, 1108; R. M. Roberts, R. H. De Wolfe, and J. H. Ross (1951). J. Am. Chem. Soc. 73, 2277; R. M. Roberts and R. H. De Wolfe, (1954). J. Am. Chem. Soc. 76, 2411; R. H. De Wolfe, Carboxylic Ortho Acid Derivatives (Academic Press, 1970).

    Google Scholar 

  12. F. B. Dains (1900). J. Am. Chem. Soc. 22, 181; F. B. Dains, R. C. Roberts, Brewster, and R. Q. (1916). J. Am. Chem. Soc. 38, 131.

    Google Scholar 

  13. S. P. Joshi, A. P. Khanolkar, and T. S. Wheeler (1936). J. Chem. Soc. 793; G. Mandel and A. J Hill (1954). J. Am. Chem. Soc. 76, 3978; A. J. Hill and J. V. Johnston (1954). J. Am. Chem. Soc. 76, 920.

  14. SMART user's manual; Siemens Industrial Automation Inc. (Madison, WI, 1994); J. Cosier and A. M. Glazer (1986). J. Appl. Cryst. 19, 105-107.

  15. G. M. Sheldrick (1990). Acta Cryst. A46, 467; G. M. Sheldrick, SHELX-96 (beta test), 1996.

    Google Scholar 

  16. For example: P. K. Mehrotra and R. Hofmann (1978). Inorg. Chem. 17, 2187; T. Yamaguchi and O. Lindqvist (1983). Acta Chem. Scand. A37, 685; B. Chiari, O. Piovesna, T. Tarantelli, and P. F. Zanazzi (1985). Inorg. Chem. 24, 366 and references therein; Y. Jiang, S. Alvarez, and R. Hofmann (1985). Inorg. Chem. 24, 749; K. M. Merz, Jr. and R. Hofmann (1988). Inorg. Chem. 27, 2120; A. Schäfer, C. Huber, G. J. Auss, and R. Ahlrichs (1993). Theor. Chim. Acta 87, 29; U. Siemeling, U. Vorfeld, B. Neumann, and H.-G. Stammler (1997). J. Chem. Soc., Chem. Commun. 1723; K. Singh, J. R. Long, and P. Stavropoulos (1997). J. Am. Chem. Soc. 119, 2942 and references therein; L. S. Ahmed, J. R. Dilworth, J. R. Miller, and N. Wheatley (1998). Inorg. Chim. Acta 278, 229; M. A. Omary, T. R. Webb, Z. Assefa, G. E. Shankie, and H. H. Patterson (1998). Inorg. Chem. 37, 1380; F. A. Cotton, X. Feng, and D. J. Timmons (1998). Inorg. Chem. 37, 4066; R. Villaneau, A. Proust, F. Robert, and P. G ouzerh (1998). J. Chem. Soc., Chem. Commun. 1491.

    Google Scholar 

  17. R. L. Griffith (1943), J. Chem. Phys. 11, 499.

    Google Scholar 

  18. A. Michaelides, V. Kiritsis, S. Skoulika, and A. Aubry (1993). Angew. Chem. Int. Ed. 32, 1495.

    Google Scholar 

  19. A. F. M. J. van der Ploeg, G. van Koten, and A. L. Spek (1979). Inorg. Chem. 18, 1052; L. M. Engelhardt, G. E. Jacobsen, W. C. Patalinghug, B. W. Skelton, C. L. Raston, and A. H. White (1991). J. Chem. Soc., Dalton Trans. 2859; J. A. Schuerman, F. R. Fronczek, and J. Selbin (1989). Inorg. Chim. Acta 160, 43.

    Google Scholar 

  20. For example: H. Schollhorn, U. Thewalt, and B. Lippert (1984). J. Chem. Soc., Chem. Commun. 769; X.-M. Chen and T. C. W. Mak (1991). J. Chem. Soc., Dalton Trans. 3253; N. J. Calos, C. H. L. Kennard, and T. C. W. Mak (1989). Aust. J. Chem. 42, 2047.

  21. C.-M. Che, H.-K. Yip, V. W.-W. Yam, P.-Y. Cheung, T.-F. Lai, S.-J. Shieh, and S.-M. Peng (1992). J. Chem. Soc., Dalton Trans. 427.

  22. H. H. Murray, R. G. Raptis, and J. P. Fackler (1988). Inorg. Chem. 27, 26.

    Google Scholar 

  23. A. J. Amoroso, J. C. Jeffery, P. L. Jones, J. A. McCleverty, E. Psilakis, and M. D. Ward (1995). J. Chem. Soc., Chem. Commun. 1175; E. R. Humphrey, N. C. Harden, L. H. Rees, J. C. Jeffery, J. A. McCleverty, and M. D. Ward (1998). J. Chem. Soc., Dalton Trans. 3353.

  24. C.-M. Che, H.-K. Yip, D. Li, S.-M. Peng, G.-H. Lee, Y.-W. Wang, and S.-T. Liu (1991). J. Chem. Soc., Chem. Commun. 1615.

  25. C. King, J. C. Wang, N. I. M. Khan, and J. P. Fackler (1989). Inorg. Chem. 28, 2145.

    Google Scholar 

  26. M. Kilner and A. Pietrzykowski (1983). Polyhedron 2, 1379.

    Google Scholar 

  27. E. K. Fields and S. Meyerson (1976). J. Org. Chem. 41, 916.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Kansas, Lawrence, KS, 66045, USA

    Stephen J. Archibald & Daryle H. Busch

  2. Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK

    Nathaniel W. Alcock

  3. Dry Media Systems Laboratory, Imation Corporation, St Paul, MN, 55144, USA

    David R. Whitcomb

Authors
  1. Stephen J. Archibald
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nathaniel W. Alcock
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Daryle H. Busch
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. David R. Whitcomb
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Archibald, S.J., Alcock, N.W., Busch, D.H. et al. Synthesis and Characterization of Silver(I) Complexes with C-Alkyl Functionalized N,N′-Diphenylamidinates: Tetrameric and Trimeric Structural Motifs. Journal of Cluster Science 11, 261–283 (2000). https://doi.org/10.1023/A:1009085319864

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1009085319864

Search

Navigation