Crystal and molecular structures of two triorganophosphinegold(I) 2-amino-cyclopent-1-ene-1-carbodithioates

Zeitschrift fur Kristallographie

Volumn 219, Issue 8, 2004, Pages 513-518

  Ho, Soo Yei ^a   Tiekink, Edward R T ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Carbodithioate; Crystal and molecular structure analysis; Gold; Phosphine; X ray diffraction

Indexed keywords

2 AMINOCYCLOPENT 1 ENE 1 CARBODITHIOATE; COORDINATION COMPOUND; GOLD DERIVATIVE; PHOSPHINE DERIVATIVE; TRIORGANOPHOSPHINEGOLD; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; GEOMETRY; HYDROGEN BOND; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 8744237276     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.219.8.513.38333     Document Type: Article

References (64)

1. Schmidbaur, H. (Ed.): Gold: Progress in Chemistry, Biochemistry and Technology. John Wiley & Sons, New York, 1999.
2. Haynes, D. R.; Whitehouse, M. W.: Gold(I) thiolates: slow-acting anti-arthritic drugs. In: Rainsford K. D.; Velo, G. P. Eds. New Developments in Antirheumatic Therapy. Inflammation and Drug Therapy Series. Volume III. Kluwer Academic Publishers, Dordrecht (1989) 207-233.
3. Sadler, P. J.; Sue, R. E.: The chemistry of gold drugs. Metal-Based Drugs 1 (1994) 107-144.
4. Shaw, III, C. F.: Gold-based therapeutic agents. Chem. Rev. 99 (1999) 2589-2600.
5. McKeage, M. J.; Maharaj, L.; Berners-Price, S. J.: Mechanisms of cytotoxicity and antitumor activity of gold(I) phosphine complexes: the possible role of mitochondria. Coord. Chem. Rev. 232 (2002) 127-135.
6. Tiekink, E. R. T.: Gold compounds in medicine: potential antitumour agents. Gold Bull. 36 (2003) 117-124.
7. Tiekink, E. R. T.: Gold derivatives for the treatment of cancer. Crit. Rev. Oncol./Hematol. 42 (2002) 225-248.
8. Tiekink, E. R. T.: Phosphinegold(I) thiolates - pharmacological use and potential. Bioinorg. Chem. Applns 1 (2003) 53-67.
9. Okinaka, Y.; Hoshino, M.: Some recent topics in gold plating for electronics applications. Gold Bull. 31 (1998) 3-13.
10. Deaton, J. C.; Luss, H. R.: Gold(I) coordination compounds with mesoionic thiolate ligands and the crystal and molecular structure of bis(1,4,5-trimethyl-1,2,4-triazolium-3-thiolate)gold(I) tetrafluoroborate. J. Chem. Soc., Dalton Trans (1999) 3163-3167.
11. Forward, J. M.; Fackler, Jr, J. P.; Assefa, Z.: in Optoelectronic Properties of Inorganic Compounds. D. M. Roundhill, D. M.; Fackler, Jr, J. P. (Eds) Plenum Press, New York, Chp. 6 (1999) 195-229.
12. Mansour, M. A.; Connick, W. B.; Lachicotte, R. J.; Gysling, H. J.; Eisenberg, R.: Linear Chain Au(I) Dimer Compounds as Environmental Sensors: A Luminescent Switch for the Detection of Volatile Organic Compounds. J. Am. Chem. Soc. 117 (1997) 1329-1330.
13. Yam, V. W.-W.; Li, C.-K.; Chan, C.-L.: Proof of potassium ions by luminescence signaling based on weak gold-gold interactions in dinuclear gold(I) complexes. Angew. Chem. Int. Ed. 37 (1998) 2857-2859.
14. Aizenberg, J.; Black, A. J.; Whitesides, G. M.: Controlling local disorder in self-assembled monolayers by patterning the topography of their metallic supports. Nature 394 (1998) 868-871.
15. Tokuhisa, H.; Zhao, M.; Baker, L. A.; Phan, V. T.; Dermody, D. L.; Garcia, M. E.; Peez, R. F.; Crookes, R. M.; Mayer, T. M.: Preparation and characterization of dendrimer monolayers and dendrimer-alkanethiol mixed monolayers adsorbed to gold. J. Am. Chem. Soc. 120 (1998) 4492-4501.
16. Schoenfisch, M. H.; Pemberton, J. E.: Air stability of alkanethiol self-assembled monolayers on silver and gold surfaces. J. Am. Chem. Soc. 120 (1998) 4502-4513.
17. Aizenberg, J.; Black, A. J.; Whitesides, G. M.: Oriented growth of calcite controlled by self-assembled monolayers of functionalized alkanethiols supported on gold and silver. J. Am. Chem. Soc. 121 (1999) 4500-4509.
18. Yam, V. W.-W.; Cheng, E. C.-C.: Molecular gold-multinuclear gold(I) complexes. Angew. Chem. Int. Ed. 39 (2000) 4240-4244.
19. 3[dσ * pσ] excited state of binuclear gold(I) complexes with bridging bis(dicyclohexylphosphino)-methane ligands: emission and time-resolved absorption spectroscopic studies. Chem. Eur. J. 7 (2001) 4656-4664.
20. 2] and (TPA)AuCl (TPA = 1,3,5-triaza-7- phosphaadamantane) Inorg. Chem. 41 (2002) 6274-6280.
21. White-Morris, R. L.; Slender, M.; Tinti, D. S.; Balch, A. L.; Rios, D.; Attar, S.: New structural motifs in the aggregation of neutral gold(I) complexes: structures and luminescence from (alkyl isocyanide)AuCN. Inorg. Chem. 41 (2003) 3237-3244.
22. 6) with distinct luminescence. J. Am. Chem. Soc. 125 (2003) 1033-1040.
23. Lee, Y.-A.; Eisenberg, R.: Luminescence tribochromism and bright emission in gold(I) thiouracilate complexes. J. Am. Chem. Soc. 125 (2003) 7778-7779.
24. Yam, V. W.-W.; Yip, S.-K.; Yuan, L.-H.; Cheung, K.-C.; Zhu, N.; Cheung, K.-K.: Synthesis, structure, and ion-binding properties of luminescent gold(I) alkynylcalix[4]crown-5 complexes. Organometallics 22 (2003) 2630-2637.
25. Liau, R.-Y.; Schier, A.; Schimdbaur, H.: Oligomerization of digoldacetylide complexes through angular head-to-tail aurophilic bonding. Organometallics 22 (2003) 3199-3204.
26. Smyth, D. R.; Vincent, B. R.; Tiekink, E. R. T.: Solvent mediated disruption of intermolecular associations in phosphinegold(I) thiolates: the relative importance of carboxylic acid dimer formation on crystal structure. CrystEngComm 2 (2000) 115-120.
27. Srnyth, D. R.; Hester, J.; Young, Jr, V. G.; E. R. T. Tiekink, E. R. T.: Tuning aurophilic interactions in dinuclear phosphine-gold(I) thiolates containing hydrogen bonding functionalities. CrystEngComm 4 (2002) 517-521.
28. Schmidbaur, H.: High-carat gold compounds. Chem. Soc. Rev. 24 (1995) 391-400.
29. Schmidbaur, H.: Supramolecular chemistry: going for gold. Nature 413 (2001) 31-33.
30. Schneider, W.; Bauer, A.; Schmidbaur, H.: (Isocyanide)gold(I) thiosalicylates: supramolecular assembly based on both auriophilic and hydrogen bonding. Organometallics 15 (1996) 5445-5446.
31. Hollatz, C.; Schier, A.; Schmidbaur, H.: Aggregation of a neutral gold(I) complex through cooperative action of hydrogen bonding and auriophilicity. J. Am. Chem. Soc. 119 (1997) 8115-8116.
32. Hollatz, C.; Schier, A.; Riede, J.; Schmidbaur, H.: Self-assembly of triatomic gold units as supporting frames for a large gold diphenylphosphinite cage molecule. J. Chem. Soc., Dalton Trans (1999) 111-114.
33. Schmidbaur, H.: The aurophilicity phenomenon: a decade of experimental findings, theoretical concepts and emerging applications. Gold Bull. 33 (2000) 3-10.
34. Cookson, P. D.; Tiekink, E. R. T.: X-ray crystal structure of (6-n-propyl-2-thiouracilato)(triethylphosphine)gold(I). J. Crystallogr. Spectros. Res. 23 (1993) 231-234.
35. B.-C. Tzeng, B.-C.; Schier, A.; Schmidbaur, H.: Crystal engineering of gold(I) thiolate based compounds via cooperative aurophilic and hydrogen-bonding interactions. Inorg. Chem. 38 (1999) 3978-3984.
36. 3. J. Chem. Soc., Dalton Trans (2000) 1579-1585.
37. 3 ligands, forming extended nets in one-, two-, and three-dimensions. J. Chem. Soc., Dalton Trans (2000) 1587-1594.
38. Lai, C. S.; Tiekink, E. R. T.: Supramolecular association in organomercury(II) 1,1-dithiolates. Complementarity between Hg.. .S and hydrogen bonding interactions in organomercury(II) 2-amino-cyclopent-1-ene-1- carbodithioates. CrystEngComm 5 (2003) 253-261.
39. Al-Saády, A. K.; McAuliffe, C. A.; Parish, R. V.; Sandbank, J. A.: A general synthesis for gold(I) complexes. Inorg. Synth. 23 (1985) 191-194.
40. Takeshima, T.; Yokoyama, M.; Imamoto, T.; Akano, M.; Asaba, H.: Reaction of active methylene compounds with carbon disulfide in the presence of ammonia. III. Reaction of cyclopentanone and cycloheptanone. J. Org. Chem. 34 (1969) 730-732.
41. Nag, K.; Joardar, D. S.: Metal complexes of sulfur-nitrogen chelating agents. I. 2-Aminocyclopentene-1-dithiocarboxylic acid complexes of nickel (II), palladium(II), and platinum(II). Inorg. Chim. Acta 14 (1975) 133-141.
42. SMART & SAINT. Software Reference Manuals. Version 5.0, Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, U.S.A., 2000.
43. Sheldrick, G. M. SADABS. A software for empirical absorption correction. University of Göttingen, Germany, 2000.
44. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; García-Granda, S.; Smits, J. M. M.; Smykalla, C.: The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands, 1992.
45. Sheldrick, G. M. SHELXL97. Program for crystal structure refinement. University of Göttingen, Germany, 1997.
46. Flack, H. D.: On enantiomorph-polarity estimation. Acta Crystallogr. A39 (1983) 876-881.
47. Johnson, C. K.: ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, 1976.
48. DIAMOND, Visual Crystal Structure Information System, Version 2.1e, CRYSTAL IMPACT, Postfach 1251, D-53002 Bonn, Germany, 2002.
49. teXsan, Single crystal structure analysis software for Windows, Version 1.05. Molecular Structure Corporation, The Woodlands, Texas, 1997.
50. Spek, T.: PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2003.
51. Bondi, A.: van der Waals volumes and radii. J. Phys. Chem. 68 (1964) 441-451.
52. Evans, D. G.; Boeyens, J. C. A.: Conformational analysis of ring pucker. Acta Crystallogr. B45 (1989) 581-590.
53. n] (n = 1, 2) compounds in solution. Inorg. Chim. Acta 192 (1992) 271-282.
54. n mit einzahnig und zweizähnig gebundenem dithiocarboxylat-ligand. Chem. Ber. 120 (1987) 97-104.
55. Wijnhoven, J. G.; Bosman, W. R.; Beurskens, P. T.: Crystal and molecular structure of (triphenylphosphine)(N,N-diethyldithiocarbamato)gold(I). J. Cryst. Mol. Struct. 2 (1972) 7-15.
56. Ho, S. Y.; Tiekink, E. R. T.: (N,N-Diethyldithiocarbamato)- (tricyclohexylphosphine)gold(I). Acta Crystallogr. E57 (2001) m603-m604.
57. Ho, S. Y.; Tiekink, E. R. T.: (N,N-Diethyldithiocarbamato)-[tris(p- methoxyphenyl)phosphine]gold(I). Acta Crystallogr. E58 (2002) m86-m87.
58. 8). Z. Kristallogr. NCS 219 (2004) 73-74.
59. 2. Z. Kristallogr. NCS 217 (2002) 359-360.
60. Tiekink, E. R. T.: Crystal structure of (triphenylphosphine)-(O- methyldithiocarbonato)gold(I). Z. Kristallogr. 173 (1985) 243-247.
61. 7). Z. Kristallogr. 203 (1993) 117-119.
62. 11), R = Et, Ph and c-hexyl. Z. Kristallogr. 204 (1993) 95-105.
63. 2COR), R = Et, nPr and iPr. Z. Kristallogr. 205 (1993) 261-270.
64. de Vos, D.; Ho S. Y.; Tiekink, E. R. T.: Cytotoxicity profiles for a series of triorganophosphinegold(I) dithiocarbamates and triorganophosphinegold(I) xanthates. Bioinorg. Chem. Applns. 2 (2004) 141-154.