Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2005 | 3 | 1 | 174-187
Tytuł artykułu

Aromatic λ3 heterocycles XIV. Fosfinine-ether macrocyclesheterocycles XIV. Fosfinine-ether macrocycles

Treść / Zawartość
Warianty tytułu
Języki publikacji
The geometry and electronic structure of several phosphinine-ether macrocycles were investigated at semiempirical level. The calculated geometries are in good agreement with experimental data. Compared to phosphinine, the coordinative abilities of phosphinineether macrocycles based on energy considerations suggest a little lowered π acceptor character, while π donor character is improved. The molecular environment causes a significant mixing of phosphinine and phenyl substituent π levels. The geometry and electronic properties of phosphinine-ether macrocycles can provide significant host coordination properties for guest species.

Opis fizyczny
  • Institute of Chemistry, Romanian Academy, 24 Mihai Viteazul Ave., 300223, Timisoara, Romania,
  • Institute of Chemistry, Romanian Academy, 24 Mihai Viteazul Ave., 300223, Timisoara, Romania
  • [1] J.M. Lehn: “Toward complex matter: supramolecular chemistry and self organization”, Proc. Natl. Acad. Sci., Vol. 99, (2002), pp. 4763–4768.[Crossref]
  • [2] N. Avarvari, N. Maigrot, L. Ricard, F. Mathey and P. Le Floch: “Synthesis and X-Ray Crystal Structures of Silacalix[n]phosphinines: The first sp2 Based Phosphorus Macrocycles”, Chem. Eur. J., Vol. 5, (1999), pp. 2109–2118.<2109::AID-CHEM2109>3.0.CO;2-Q[Crossref]
  • [3] N. Mezailles, N. Maigrot, S. Hamon, L. Ricard, F. Mathey and P. Le Floch: “Mixed Phosphinine-Ether Macrocycles”, J. Org. Chem., Vol. 66, (2000), pp. 1054–1056.[Crossref]
  • [4] N. Avarvari, N. Maigrot, L. Ricard, P. Le Floch and F. Mathey: “Silacalix[n]-phosphaarenes: Macrocyclic Ligands Based on Dicoordinate Phosphorus Centres”, Science, Vol. 280, (1998), pp. 1587–1589.[Crossref]
  • [5] M. Ciampolini: “Stereochemical aspects of macrocyclic polyphosphanes and polyarsanes and of their metal complexes”, Pure and Appl. Chem., Vol. 58, (1986), pp. 1429–1436.
  • [6] E.N. Tsvetkov, A.N. Bovin and V.Kh. Syundyukova: “The Synthesis and Complex Forming Capacity of Phosphorus-containing Macrocycles”, Russ. Chem. Rev., Vol. 57(8), (1968), pp. 776–800.[Crossref]
  • [7] C. Bonninague, D. Houala and R. Wolf: “Bicyclic Phosphanes. Part 2.1Spontaneous Dimerization of a Constrained Bicyclic Phosphane. The Crystal and Molecular Structure of a Tricyclic Compound containing the Dioxadiazadiphosphecine Ring”, J. Chem. Soc. Perkin Trans. II, (1983), pp. 773.
  • [8] H.J. Christau, L. Chiche, F. Fallouh, P. Hullot, G. Renard and H. Christol: “Mise au point d’une methode de synthese controlee de ligands macrocycliques polyphosphores. Application a la preparation de macrocycles diphosphores polyoxygenes”, Nuveau Journal de Chimie, Vol. 8, (1984), pp. 191–195.
  • [9] J.W.H.M. Viterwijk, S. Harkema and D. Feil: “A Molecular Mechanics Study of 18-Crown-6 and its Complexes with Neutral Organic Molecules”, J. Chem. Soc. Perkin Trans II, (1987), pp. 721–731.
  • [10] L. Wei, A. Bell, S. Warner, I.D. Williams and S.J. Lippard: “Aza- and Oxaphosphands, a New Class of Hard/Soft Binucleating Phosphine Macrocycles”, J. Am. Chem. Soc., Vol. 108, (1986), pp. 8302–8303.[Crossref]
  • [11] J.P. Dutasta: “Dimerisation et reaction d’ouverture des cycles dioxaphpsphocannes-1,3,2. Application a la synthese de thiono-phosphonates macrocycliques a 16 et 24 chainons”, J. Chem. Res., (1986), pp. 361–365.
  • [12] L. Wei, A. Bell, K.-H. Ahn, M.M. Holl, S. Warner, I.D. Williams and S.J. Lippard. “Synthesis, Isomer Separation, and Metal Complexation Studies of Aza-and Oxaphosphands, a Class of Hard/Soft Dinucleating Phosphine Macrocycles”, Inorg. Chem., Vol. 29, (1990), pp. 825–837.[Crossref]
  • [13] A.J. Ashe III: “The group V heterobenzenes”, Acc. Chem. Res., Vol. 11, (1978), pp. 153.[Crossref]
  • [14] H. Oehling, W. Schäfer and A. Schweig: “Sequence of highest occupied molecular orbital in the phosphorins system”, Angew. Chem. Int. Ed. Engl., Vol. 10, (1971), pp. 656–657.[Crossref]
  • [15] C. Batich, E. Heilbronner, V. Hornung, A.J. Ashe III, D.T. Clark, K.T. Cobley, D. Kilcast and I. Scanlan: “Photoelectron spectra of Phosphabenzene, Arsabenzene and Stibabenzene”, J. Am. Chem. Soc., Vol. 95, (1973), pp. 928.[Crossref]
  • [16] H.-L. Hase, A. Schweig, H. Hahn and J. Radloff: “Die elektronenstruktur des Arsenins(Arsabenzols)”, Tetrahedron, Vol. 29, (1973), pp. 475–477.[Crossref]
  • [17] H. Öhling and A. Schweig: “A CNDO/2 Approach to the Electronic structure of phosphabenzenes”, Tetrahedron Lett., Vol. 56, (1970), pp. 4941–4944.[Crossref]
  • [18] C. Elsenbroich, S. Voss, O. Schiemann, A. Lippek and K. Harms: “η 1-Coordination of Phosphinine to Chromium, Molybdenum and Tungsten”, Organometallics, Vol. 17, (1998), pp. 4417–4424.[Crossref]
  • [19] C. Elsenbroich, M. Nowotny, A. Behrendt, W. Massa and S. Wocadlo: “Tetrakis (η 1-phosphabenzene)nickel”, Angew. Chem. Int. Ed. Engl., Vol. 31, (1992), pp. 1343–1345.[Crossref]
  • [20] C. Elsenbroich, M. Nowotny, J. Kroker, A. Behrendt, W. Massa and S. Wocadlo: “Hexakis(η 1-phosphinin)chrom: Syntese, Structur, und redox verhalten”, J Organometallic Chem., Vol. 459, (1993), pp. 157–167.[Crossref]
  • [21] D. Böhm, H. Geiger, F. Knoch, F. Kremer, S. Kummer, P. Le Floch, F. Mathey, U. Schmidt and U. Zenneck: “η 6-Phosphinine and η 6-1,3-Diphosphinine Iron Complexes”, Phosphorus Sulfur, Vol. 109–110, (1996), pp. 173–176.
  • [22] A.J. Ashe III and C. Colburn: “Molybdenum-Carbonyl Complexes of the Group 5 Heterobenzenes”, J. Am. Chem. Soc., Vol. 99, (1977), pp. 8099–8100.[Crossref]
  • [23] O. Scherer: “Phosphorus, Arsenic, Antimony and Bismut Multiply Bonded Systems with Low Coordinate Number and Their Role as Complex Ligands”, Angew. Chem. Int. Ed. Engl., Vol. 24, (1985), pp. 924–943.[Crossref]
  • [24] P. Le Floch and F. Mathey: “Transition Metals in Phosphinine Chemistry”, Coord. Chem. Rev., Vol. 179–180, (1998), pp. 771–791.
  • [25] P. Rosa, N. Mezailles, L. Ricard, F. Mathey, P. Le Floch and and Y. Jean: “Dianionic Iron and Ruthenium(2−) Biphosphinine Complexes: A Formal d10 Ruthenium Complex”, Angew. Chem. Int. Ed. Engl., Vol. 40, (2001), pp. 1251–1253.<1251::AID-ANIE1251>3.0.CO;2-H
  • [26] P. Rosa, N. Mezailles, L. Ricard, F. Mathey and P. Le Floch: “A 2,2′-Biphosphinine Dianion: Synthesis and Reactivity”, Organometallics, Vol. 18, (1999), pp. 3348–3352.[Crossref]
  • [27] J. Walluk, H.-P. Klein, A.J. Ashe and J. Michl: “Effective Electronegativities of Phosphorus, Arsenic, and Antimony in a π System. Evidence from Magnetic Circular Dichroism”, Organometallics, Vol.8, (1989), pp. 2804–2808.[Crossref]
  • [28] G. Frisson, A. Sevin, N. Avarvari, F. Mathey and P. Le Floch: “The CH by N replacement effects on the aromaticity and reactivity of phosphinines”, J. Org. Chem., Vol. 64, (1999), pp. 5524–5529.[Crossref]
  • [29] N. Mezailles, N. Avarvari, N. Maigrot, L. Ricard, F. Mathey, P. le Floch, L. Cataldo, T. Berelaz and M. Geoffroy: “Gold(I) and Gold(0) Complexes of Phosphinine-Based Macrocycles”, Angew. Chem. Int. Ed., Vol. 38, (1990), pp. 3194–3197.<3194::AID-ANIE3194>3.0.CO;2-O
  • [30] L. Cataldo, S. Choua, T. Berclaz, M. Geoffroy, N. Mezailles, L. Ricard, F. Mathey and P. Le Floch: “Formation and Structure of Rh(0) Complexes of Phosphinine-Containing Macrocycles: EPR and DFT investigations”, J. Phys. Chem. A, Vol. 106, (2002), pp. 3107–3027.
  • [31] A. Moores, N. Mezailles, N. Maigrot, L. Richard, F. Mathey and P. Le Floch: “Synthesis and Reactivity Towards Cationic Group 11 metal Centers of an Extended Silacalix-[3]-phosphinine macrocycle”, Eur. J. Inorg. Chem., (2002), pp. 2034–2039.
  • [32] L. Cataldo, S. Choua, T. Berclaz, M. Geoffroy, N. Mezailles, L. Ricard, F. Mathey and P. Le Floch: “Formation of a Phosphorus-Phosphorus Bond by Succesive One-Electron Reductions of a two-Phosphinines-Containing Macrocycle: Crystal Structures, EPR, and DFT Investigations”, J. Am. Chem. Soc., Vol. 123, (2001), pp. 6654–6661.[Crossref]
  • [33] D. Gudat, S. Häp, L. Szarvas and M. Nieger: “Ambident σ- and π-donor ability of a neutral 10π-aromatic phosphoniobenzophospholide”, Chem. Commun.,(2000), pp. 1637–1638.
  • [34] S.B. Clendening, J.C. Green and J.F. Nixon: “A comparison of C3R3P3 and C6R3H3as ligands using photoelectron spectroscopy and density functionaltheory”, J. Chem. Soc. Dalton Trans., (2000), pp. 1507–1512. [Crossref]
  • [35] M. Al-Ktaifani, J.G. Green, P.B. Hitchcock and J.F. Nixon: “Electronic structure of [M(η-P3C2Bu 2t)(CO3)](M=Mn or Re): a study by photoelectron spectroscopy and density functional calculations”, J. Chem. Soc. Dalton Trans., (2001), pp. 1726–1731. [Crossref]
  • [36] D.J. Berger, P.P. Gaspar and J.F. Liebman: “π-Overlap, pyramidalization and protonation of Group 15 heterocycles. The basicity of the “higher pyridines””, J. Mol. Struct. (Theochem), Vol. 338, (1995), pp. 51–70.[Crossref]
  • [37] Z. Zhou and R. G. Parr: “The new measures of aromaticity: Absolute hardness and relative hardness”, J. Am. Chem. Soc., Vol. 111, (1989), pp. 7371–7379.[Crossref]
  • [38] M. Mracec, M. Mracec and Z. Simon: “Aromatic λ3-Heterocycles. VII. Chemical Reactivity of Heterobenzenes Containing Heteroatoms of 15th Group”, Annals of Western Univ. of Timisoara, Ser. Chim., Vol. 5, (1996), pp. 99–108.
  • [39] Numbering of the phosphinine-ether macrocycles have been done with Auto Nom 2000 program version 5.0, MDL-Information Systems GmbH.
  • [40] HyperChem TM Release 5.11, Professional for Windows, Hypercube, Inc., Gainesville, Fl. 32601, USA, 1999.
  • [41] HyperChemRelease 7, COR016-118GM274305.
  • [42] M. Mracec and Z. Simon: “Hybridization of dicoordinated trivalent and tetracoordinated pentavalent phosphorus in conjugated six-membered rings”, Rev. Roum. Chim., Vol. 23, (1978), pp. 769–779.
  • [43] MOPAC 6.0; J.J. Stewart, QCPE program 455.
  • [44] D.S. Warren and B.M. Gimarc: “Valence Isomers of Benzene and Their Relationship to Isomers of Isoelectronic P6”, J. Am. Chem. Soc., Vol. 114, (1992), pp. 5378–5385.[Crossref]
Typ dokumentu
Identyfikator YADDA
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.