Skip to main content
SpringerLink
Log in

Metal complexes of corroles and other corrinoids

  • Chapter
  • First Online:
Metal Complexes with Tetrapyrrole Ligands III

Part of the book series: Structure and Bonding ((STRUCTURE,volume 84))

Abstract

Several tetrapyrroles are employed by Nature to carry out fundamental biological functions and synthetic models compounds have been extensively used in order to understand the mechanisms of action of natural systems.

One of the structures present in many enzymes is the corrinoid structure. It consists of a tetrapyrrolic macrocycle, where a direct link between two pyrrole rings exists. Such a direct link and the different degrees of unsaturation that can be introduced into the macrocycle modulate its chelating properties towards metal ions and its reactivity.

A most interesting example of the corrinoid structure is corrole, a macrocycle where an 18 electron aromatic π system analogous to that of a porphyrin is maintained. Corrole has been shown to be a versatile ligand capable of coordinating transition and main group metals without significant distortion of the macrocycle plane.

The present article reviews the developments of the chemistry of corrole and its metal complexes considering the synthetic procedures that can be followed in order to prepare such compounds, their spectroscopic characterization and redox reactivity and demonstrates the peculiar ligand field effect of this macrocycle.

The chemistry of other synthetic corrinoids is also reviewed with special attention to their preparation procedures and axial ligand binding reactions.

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

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

7 References

  1. Stolzenberg AM, Stershic MT (1988) J Am Chem Soc 110: 6391 and Refs. therein

    Article  CAS  Google Scholar 

  2. Murakami Y, Aoyama Y, Tokunaga K (1980) J Am Chem Soc 102: 6736

    Article  CAS  Google Scholar 

  3. Johnson AW (1967) Chem in Britain 3: 253

    CAS  Google Scholar 

  4. Johnson AW, Kay IT (1965) J Chem Soc 1620

    Google Scholar 

  5. Battersby AR (1986) Acc Chem Res 19: 147

    Article  CAS  Google Scholar 

  6. Harrison HR, Hodder OJR, Hodgkin DC (1971) J Chem Soc B 640

    Google Scholar 

  7. Johnson AW (1975) In: Smith KM (ed) Porphyrins and metalloporphyrins. Elsevier, Amsterdam, p 729

    Google Scholar 

  8. Grigg R (1978) In: Dolphin DH (ed) The porphyrins, vol II. Academic Press, NY

    Google Scholar 

  9. Jackson AH (1978) In: Dolphin DH (ed) The porphyrins, vol I. Academic Press, NY, p 341

    Google Scholar 

  10. Genokhova NS, Melent'eva TA, Berezowskii VM (1980) Russ Chem Rev 49: 1056

    Article  Google Scholar 

  11. Melent'eva TA (1983) Russ Chem Rev 52: 641

    Article  Google Scholar 

  12. Woodward RB (1973) Pure Appl Chem 33: 145

    CAS  Google Scholar 

  13. Golding BT (1979) In: Haslam E (ed) Comprehensive organic chemistry. Pergamon, Oxford, p 549

    Google Scholar 

  14. Fuhrer W, Schneider P, Schilling W, Wild H-J, Naag H, Obata N, Holmes A, Schreiber J, Eschenmoser A (1972) Chimia 26: 320

    Google Scholar 

  15. IUNPAC-IUB Commission for Chemical Nomenclature (1974) Biochemistry 13: 1555

    Article  Google Scholar 

  16. Bonnet R (1978) In: Dolphin DH (ed) The porphyrins, vol I. Academic Press, NY

    Google Scholar 

  17. Pandey RK, Zhou H, Gerzevske K, Smith KM (1992) J Chem Soc Chem Commun 183

    Google Scholar 

  18. Murakami Y, Aoyama Y, Hayashida M (1980) J Chem Soc Chem Commun 501

    Google Scholar 

  19. Grigg R, Johnson AW, Shelton G (1971) J Chem Soc (C) 2287

    Google Scholar 

  20. Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L (1967) J Org Chem 32: 476

    Article  CAS  Google Scholar 

  21. Boschi T, Licoccia S, Paolesse R, Tagliatesta P (1988) Inorg Chim Acta 141: 169

    Article  CAS  Google Scholar 

  22. Boschi T, Licoccia S, Tagliatesta P (1986) Inorg Chim Acta 119: 191

    Article  CAS  Google Scholar 

  23. Hanson LK, Gouterman M, Hanson JC (1973) J Am Chem Soc 95: 4822

    Article  CAS  Google Scholar 

  24. Boschi T, Licoccia S, Paolesse R, Tagliatesta P, Tehran MA, Pelizzi G, Vitali F (1990) J Chem Soc Dalton Trans 463

    Google Scholar 

  25. Paolesse R, Licoccia S, Boschi T (1990) Inorg Chim Acta 178: 9

    Article  CAS  Google Scholar 

  26. Buchler JW (1975) In: Smith KM (ed) Porphyrins and metalloporphyrins. Elsevier, Amsterdam, p 157

    Google Scholar 

  27. Vogel E, Will S, Schulze Tilling A, Neumann L, Lex J, Bill E, Trautwein AX, Wieghardt K (1994) Angew Chem 106: 771, Int Edn Engl 33: 731

    Article  CAS  Google Scholar 

  28. Licoccia S, Paci M, Paolesse R, Boschi T (1991) J Chem Soc Dalton Trans 461

    Google Scholar 

  29. Boschi T, Licoccia S, Tagliatesta P (1987) Inorg Chim Acta 126: 157

    Article  CAS  Google Scholar 

  30. Paolesse R, Licoccia S, Fanciullo M, Morgante E, Boschi T (1993) Inorg Chim Acta 203: 107

    Article  CAS  Google Scholar 

  31. Paolesse R, Licoccia S, Bandoli G, Dolmella A, Boschi T (1994) Inorg Chem 33: 1171

    Article  CAS  Google Scholar 

  32. Hitchcock PB, McLaughlin GM (1976) J Chem Soc Dalton Trans 1927

    Google Scholar 

  33. Matsuda Y, Yamada S, Murakami Y (1980) Inorg Chim Acta 44: L309

    Google Scholar 

  34. Conlon M, Johnson AW, Overend WR, Rajapaksa D, Elson CM (1973) J Chem Soc Perkin Trans I 2281

    Google Scholar 

  35. Buchler JW (1978) In: Dolphin DH (ed) The porphyrins, vol I. Academic Press, NY, p 389

    Google Scholar 

  36. Hush NS, Dyke JM, Williams ML, Woolsey IS (1974) J Chem Soc Dalton Trans 395

    Google Scholar 

  37. Brewer CT, Brewer GA (1988) Inorg Chim Acta 154: 67

    Article  CAS  Google Scholar 

  38. Zanoni R, Boschi T, Licoccia S, Paolesse R, Tagliatesta P (1988) Inorg Chim Acta 145: 175

    Article  CAS  Google Scholar 

  39. Macquet JP, Millard MM, Theophanides T (1978) J Am Chem Soc 100: 4741

    Article  CAS  Google Scholar 

  40. Katz JJ, Brown CE (1983) Bull Magn Res 5: 3

    CAS  Google Scholar 

  41. Botulinski A, Buchler JW, Lee YJ, Scheidt WR, Wicholas M (1988) Inorg Chem 27: 927

    Article  CAS  Google Scholar 

  42. Pawlik MJ, Miller PK, Sullivan EP, Levstik MA, Almond DA, Strauss SH (1988) J Am Chem Soc 110: 3007

    Article  CAS  Google Scholar 

  43. Dugad LB, Mehdi OK, Mitra S (1987) Inorg Chem 26: 1741

    Article  CAS  Google Scholar 

  44. Janson TR, Katz JJ (1978) In: Dolphin DH (ed) The porphyrins, vol IV. Academic Press, NY

    Google Scholar 

  45. Hush NS, Dyke JM, Williamson ML, Woolsey IS (1969) Molec Phys 17: 559

    Article  CAS  Google Scholar 

  46. Barkigia KM, Berber MD, Fajer J, Medforth CJ, Renner MW, Smith KM (1990) J Am Chem Soc 112: 8851

    Article  CAS  Google Scholar 

  47. Matsuda Y, Yamada S, Murakami Y (1981) Inorg Chem 20: 2239

    Article  CAS  Google Scholar 

  48. Murakami Y, Matsuda Y, Yamada S (1981) J Chem Soc Dalton Trans 855

    Google Scholar 

  49. Kadish KM, Koh W, Tagliatesta P, Sazou D, Paolesse R, Licoccia S, Boschi T (1992) Inorg Chem 31: 2305

    Article  CAS  Google Scholar 

  50. Hush NS, Woolsey IS (1974) J Chem Soc Dalton Trans 24

    Google Scholar 

  51. Dolphin D, Harris RLN, Huppatz JL, Johnson AW, Kay IT (1966) J Chem Soc C 30

    Google Scholar 

  52. Johnson AW, Overend WR (1972) J Chem Soc Perkin Trans I 2681

    Google Scholar 

  53. Johnson AW, Overend WR, Hamilton AL (1973) J Chem Soc Perkin Trans I 991

    Google Scholar 

  54. Dicker ID, Grigg R, Johnson AW, Pinnock H, Richardson K, van den Broek P (1971) J Chem Soc C 536

    Google Scholar 

  55. Inhoffen HH, Buchler JW, Puppe L, Rohbock K (1971) Liebigs Ann Chem 747: 133

    Article  CAS  Google Scholar 

  56. Clarke DA, Grigg R, Harris RNL, Johnson AW, Kay IT, Shelton KW (1967) J Chem Soc C 1648

    Google Scholar 

  57. Grigg R, Johnson AW, Shelton KW (1968) J Chem Soc C 1291

    Google Scholar 

  58. Johnson AW (1975) Chem Soc Rev 4: 1

    Article  CAS  Google Scholar 

  59. Johnson AW (1980) Chem Soc Rev 9: 125

    Article  CAS  Google Scholar 

  60. Gossauer A, Maschler H, Inhoffen HH (1974) Tetrahedron Lett 1277

    Google Scholar 

  61. Engel J, Inhoffen HH (1977) Liebigs Ann Chem 767

    Google Scholar 

  62. Jeyakumar D, Snow KM, Smith KM (1988) J Am Chem Soc 110: 8562 and references therein

    Article  CAS  Google Scholar 

  63. Boschi T, Paolesse R, Tagliatesta P (1990) Inorg Chim Acta 168: 83

    Article  CAS  Google Scholar 

  64. Bertele E, Boos H, Dunitz JD, Elsinger F, Eschenmoser A, Felner I, Gribi HP, Gschwend H, Meyer EF, Pesaro M, Scheffold R (1964) Angew Chem 76: 393

    Article  CAS  Google Scholar 

  65. Bertele E, Eschenmoser A, Gschwend H, Pesaro M, Scheffold R (1965) Proc Roy Soc London, Ser A 288: 306

    Article  Google Scholar 

  66. Yamada Y, Miljkovic D, Wehrli P, Golding B, Löliger P, Keese R, Müller K, Eschenmoser A (1969) Angew Chem 81: 301

    Article  Google Scholar 

  67. Eschenmoser A (1976) Chem Soc Rev 5: 377

    Article  CAS  Google Scholar 

  68. Pfaltz A, Bühler N, Neier R, Hirai K, Eschenmoser A (1977) Helv Chim Acta 60: 2653

    Article  CAS  Google Scholar 

  69. Rasetti V, Hilpert K, Fässler A, Pfaltz A, Eschenmoser A (1981) Angew Chem 93: 1108, Int Ed Engl 20: 1058

    Article  CAS  Google Scholar 

  70. Koppenhagen VB, Ernst L, Grothjan L, Dresow B (1982) Liebigs Ann Chem 1575

    Google Scholar 

  71. Rasetti V, Kräutler A, Pflatz A, Eschenmoser A (1977) Angew Chem 89: 475

    Article  CAS  Google Scholar 

  72. Kräutler B, Pfaltz A, Nordmann R, Hodgson KO, Dunitz JD, Eschenmoser A (1976) Helv Chim Acta 59: 924

    Article  Google Scholar 

  73. Kräutler B, Hilpert K (1982) Angew Chem 94: 139

    Article  Google Scholar 

  74. Ofner S, Rasetti V, Zehnder B and Eschenmoser A (1981) Helv Chim Acta 64: 1431

    Article  CAS  Google Scholar 

  75. Angst C, Kratky C, Eschenmoser A (1981) Angew Chem 93: 275, Int Edn Engl 20: 263

    Article  CAS  Google Scholar 

  76. Monforts FP (1982) Angew Chem 94: 208, Int Edn Engl 21: 214

    Google Scholar 

  77. Monforts FP, Bats JW (1987) Helv Chim Acta 70: 402

    Article  Google Scholar 

  78. Rasetti V, Pfaltz A, Kratky C, Eschenmoser A (1981) Proc Natl Acad Sci USA 78: 16

    Article  CAS  Google Scholar 

  79. Battersby AR, Matcham GWJ, McDonald E, Neier R, Thompson M, Woggon WD, Bykhovskii VYa, Morris HR (1979) J Chem Soc Chem Commun 185

    Google Scholar 

  80. Lewis NG, Neier R, Matcham GWJ, McDonald E, Battersby AR (1979) J Chem Soc Chem Commun 541

    Google Scholar 

  81. Müller G, Gneuss RD, Kriemler HP, Scott AI, Irwin AJ (1979) J Am Chem Soc 101: 3655

    Article  Google Scholar 

  82. Kräutler B (1987) Chimia 41: 277

    Google Scholar 

  83. Fujiki M, Tabei H, Isa K (1986) J Am Chem Soc 108: 1532

    Article  CAS  Google Scholar 

  84. Murakami Y, Aoyama Y, Tada T (1981) Bull Chem Soc Jpn 54: 2302

    Article  CAS  Google Scholar 

  85. Murakami Y, Aoyama Y, Tada T (1981) Inorg Chim Acta 54: L111

    Google Scholar 

  86. Elson CM, Hamilton A, Johnson AW (1973) J Chem Soc Perkin I 775

    Google Scholar 

  87. Chang CK, Wu W, Chern SS, Peng SM (1992) Angew Chem 104: 61, Int Edn Engl 31: 70

    Article  CAS  Google Scholar 

  88. Steiger B, Walder L (1992) Helv Chim Acta 75: 90

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical Sciences and Technologies, University of Rome Tor Vergata, I-00173, Rome, Italy

    S. Licoccia & R. Paolesse

Authors
  1. S. Licoccia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Paolesse
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1995 Springer-Verlag

About this chapter

Cite this chapter

Licoccia, S., Paolesse, R. (1995). Metal complexes of corroles and other corrinoids. In: Metal Complexes with Tetrapyrrole Ligands III. Structure and Bonding, vol 84. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0111331

Download citation

  • DOI: https://doi.org/10.1007/BFb0111331

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-59281-5

  • Online ISBN: 978-3-540-49229-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation