Autocatalytic degradation of white phosphorus with silylenes

Schoeller W (2009)
PHYSICAL CHEMISTRY CHEMICAL PHYSICS 11(26): 5273-5280.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Schoeller, WolfgangUniBi
Einrichtung
Fakultät für Chemie > Theoretische Chemie
Abstract / Bemerkung
White phosphorus (P-4) is prone to undergo degradation by nucleophiles and is reluctant to do so with electrophiles. Silylenes possess a strong singlet character but at the same time bear a largely inert lone pair orbital at the silicon atom. Thus they predominantly react in a similar way to electrophilic carbenes. Due to the poor pi-character of the P-P bonds in white phosphorus, the overlap with the empty orbital for the electrophilic silylene is less facile and results in a relatively large barrier for the addition reaction. The electrophilic approach of the silylene to white phosphorus is catalyzed by addition of a second P-4, forming a trigonal bipyramidal transition state geometry. Its stability towards fragmentation is essentially lower than that of the silyl cation. The entropy contributions for bimolecular versus termolecular reactions are discussed.
Erscheinungsjahr
2009
Zeitschriftentitel
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Band
11
Ausgabe
26
Seite(n)
5273-5280
ISSN
1463-9076
eISSN
1463-9084
Page URI
https://pub.uni-bielefeld.de/record/1633281

Zitieren

Schoeller W. Autocatalytic degradation of white phosphorus with silylenes. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 2009;11(26):5273-5280.
Schoeller, W. (2009). Autocatalytic degradation of white phosphorus with silylenes. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 11(26), 5273-5280. https://doi.org/10.1039/b818396a
Schoeller, Wolfgang. 2009. “Autocatalytic degradation of white phosphorus with silylenes”. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 11 (26): 5273-5280.
Schoeller, W. (2009). Autocatalytic degradation of white phosphorus with silylenes. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 11, 5273-5280.
Schoeller, W., 2009. Autocatalytic degradation of white phosphorus with silylenes. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 11(26), p 5273-5280.
W. Schoeller, “Autocatalytic degradation of white phosphorus with silylenes”, PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 11, 2009, pp. 5273-5280.
Schoeller, W.: Autocatalytic degradation of white phosphorus with silylenes. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 11, 5273-5280 (2009).
Schoeller, Wolfgang. “Autocatalytic degradation of white phosphorus with silylenes”. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 11.26 (2009): 5273-5280.

8 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Different Reactivity of As4 towards Disilenes and Silylenes.
Seitz AE, Eckhardt M, Sen SS, Erlebach A, Peresypkina EV, Roesky HW, Sierka M, Scheer M., Angew Chem Int Ed Engl 56(23), 2017
PMID: 28471032
The chemistry of cationic polyphosphorus cages--syntheses, structure and reactivity.
Holthausen MH, Weigand JJ., Chem Soc Rev 43(18), 2014
PMID: 24740160
Exploring the reactivity of white phosphorus with electrophilic carbenes: synthesis of a P4 cage and P8 clusters.
Martin CD, Weinstein CM, Moore CE, Rheingold AL, Bertrand G., Chem Commun (Camb) 49(40), 2013
PMID: 23571800
Activation of phosphorus by group 14 elements in low oxidation states.
Khan S, Sen SS, Roesky HW., Chem Commun (Camb) 48(16), 2012
PMID: 22237483
Stable singlet carbenes as mimics for transition metal centers.
Martin D, Soleilhavoup M, Bertrand G., Chem Sci 2(3), 2011
PMID: 21743834
On the mechanism of the reaction of white phosphorus with silylenes.
Szilvási T, Veszprémi T., Dalton Trans 40(27), 2011
PMID: 21660339
The mechanism and energetics of insertion reactions of silylenes.
Nyíri K, Szilvási T, Veszprémi T., Dalton Trans 39(39), 2010
PMID: 20717586
Zwitterionic and cationic P(5)-clusters from four-membered phosphorus-nitrogen-metal heterocycles.
Holthausen MH, Richter C, Hepp A, Weigand JJ., Chem Commun (Camb) 46(37), 2010
PMID: 20730242

110 References

Daten bereitgestellt von Europe PubMed Central.


Maier, Fortschr. Chem. Forsch. 19(), 1971

Lehmann, Pure Appl. Chem. 52(), 1980

Michaelis, Chem. Ber. 32(), 1899

Michaelis, Justus Liebigs Ann. Chem. 310(), 1899

Burgess, J. Chem. Soc., Trans. 79(), 1901

Brown, J. Chem. Soc., Chem. Commun. (), 1978

Brown, Phosphorus, Sulfur Silicon Relat. Elem. 6(), 1979

Fritz, Z. Anorg. Allg. Chem. 504(), 1983

Baudler, Chem. Ber. 113(), 1980

Schmidpeter, Z. Anorg. Allg. Chem. 527(), 1985

Ginsberg, J. Am. Chem. Soc. 93(), 1971

Milyukov, Russ. Chem. Rev. 74(), 2005
Coordination chemistry and functionalization of white phosphorus via transition metal complexes.
Peruzzini M, Gonsalvi L, Romerosa A., Chem Soc Rev 34(12), 2005
PMID: 16284670

Peruzzini, J. Organomet. Chem. 689(), 2004

Scherer, Chem. Unserer Zeit 34(), 2000

Scherer, Acc. Chem. Res. 32(), 1999

Whitmire, Adv. Organomet. Chem. 42(), 1998

Ehses, Top. Curr. Chem. 220(), 2002

Cummins, Angew. Chem. 118(), 2006

Cummins, Angew. Chem., Int. Ed. 45(), 2006

Figuera, Dalton Trans. (), 2006

Masuda, Angew. Chem. 119(), 2007

Masuda, Angew. Chem., Int. Ed. 46(), 2007
NHC-mediated aggregation of P4: isolation of a P12 cluster.
Masuda JD, Schoeller WW, Donnadieu B, Bertrand G., J. Am. Chem. Soc. 129(46), 2007
PMID: 17973395

Lynam, Angew. Chem. 120(), 2008

Lynam, Angew. Chem., Int. Ed. 47(), 2008

Xiong, Angew. Chem. 119(), 2007

Xiong, Angew. Chem., Int. Ed. 46(), 2007

Peng, Angew. Chem. 116(), 2004

Peng, Angew. Chem., Int. Ed. 43(), 2004

Dohmeier, Angew. Chem. 106(), 1994

Dohmeier, Angew. Chem., Int. Ed. Engl. 33(), 1994

Arduengo,, J. Am. Chem. Soc. 113(), 1991

Uhl, Chem. Commun. (), 1999

Lavallo, Angew. Chem. 117(), 2005

Lavallo, Angew. Chem., Int. Ed. 44(), 2005

Lavallo, Angew. Chem. 117(), 2005

Lavallo, Angew. Chem., Int. Ed. 44(), 2005

Stock, Ber. Deutsch. Chem. Ges. 42(), 1909

Kira, J. Am. Chem. Soc. 121(), 1999

Denk, J. Am. Chem. Soc. 116(), 1994

Hill, J. Organomet. Chem. 689(), 2004

Gehrhus, Dalton Trans. (), 2006

Moss, Acc. Chem. Res. 13(), 1980

Moss, Acc. Chem. Res. 22(), 1989

Rondan, J. Am. Chem. Soc. 102(), 1980

Sander, J. Phys. Org. Chem. 13(), 2000

Oláh, THEOCHEM 771(), 2006

Hoffmann, J. Am. Chem. Soc. 90(), 1968

Kostikov, Zh. Org. Khim. 13(), 1977

Kostikov, Russ. J. Org. Chem. (), 1977

Schoeller, J. Chem. Soc., Chem. Commun. (), 1982

Schoeller, Z. Naturforsch. B 35B(), 1980

Schoeller, Angew. Chem. 93(), 1981

Schoeller, Angew. Chem., Int. Ed. Engl. 20(), 1981

Kettle, Theor. Chim. Acta 4(), 1966

Schmidtke, Theor. Chim. Acta 9(), 1968

Jotham, Chem. Soc. Rev. 2(), 1973

Pauling, J. Am. Chem. Soc. 54(), 1932

Pauling, J. Chem. Phys. 20(), 1952

Moffitt, Trans. Faraday Soc. 44(), 1948

Gimarc, Phosphorus, Sulfur Silicon Relat. Elem. 93–94(), 1994

Guest, J. Chem. Soc., Faraday Trans. 2 68(), 1972

Hillier, J. Chem. Soc., Chem. Commun. (), 1970

Schoeller, Inorg. Chem. 25(), 1986

Brundle, Inorg. Chem. 11(), 1972

Evans, Int. J. Mass Spectrom. Ion Phys. 9(), 1972

Hart, J. Chem. Phys. 42(), 1965

Olsson, J. Am. Chem. Soc. 117(), 1995

Ottosson, Organometallics 15(), 1996

Olsson, Chem. Phys. Lett. 215(), 1993

Kutzelnigg, Angew. Chem. 96(), 1984

Kutzelnigg, Angew. Chem., Int. Ed. Engl. 23(), 1984

Magnusson, J. Am. Chem. Soc. 106(), 1984

Magnusson, J. Am. Chem. Soc. 106(), 1984

Schoeller, Inorg. Chem. 26(), 1987

Schoeller, Inorg. Chem. 26(), 1987

Haeser, J. Am. Chem. Soc. 114(), 1992

Boecker, Z. Anorg. Allg. Chem. 621(), 1995

Haeser, J. Am. Chem. Soc. 116(), 1994

Schäfer, J. Chem. Phys. 100(), 1994

Becke, Phys. Rev. A: At., Mol., Opt. Phys. 38(), 1988

Head-Gordon, Chem. Phys. Lett. 220(), 1994

Saebo, Chem. Phys. Lett. 154(), 1989
Stable silylenes.
Haaf M, Schmedake TA, West R., Acc. Chem. Res. 33(10), 2000
PMID: 11041835

Hill, J. Organomet. Chem. 689(), 2004

West, Pure Appl. Chem. 68(), 1996

Veszpremi, Adv. Molec. Struct. Res. 6(), 2000

Veszpremi, J. Phys. Chem. 100(), 1996

Heinemann, J. Organomet. Chem. 475(), 1994
Double-hybrid density functionals with long-range dispersion corrections: higher accuracy and extended applicability.
Schwabe T, Grimme S., Phys Chem Chem Phys 9(26), 2007
PMID: 17664963

Fritsche, Int. J. Quantum Chem. 100(), 2004
Systematic errors in computed alkane energies using B3LYP and other popular DFT functionals.
Wodrich MD, Corminboeuf C, von Rague Schleyer P., Org. Lett. 8(17), 2006
PMID: 16898778

Grafenstein, J. Chem. Phys. 127(), 2007

Simon, J. Chem. Phys. 105(), 1996

Boys, Mol. Phys. 19(), 1970

Schoeller, Chem. Ber. 130(), 1997

Damrauer, Organometallics 27(), 2008

Chan, Angew. Chem. 119(), 2007

Chan, Angew. Chem., Int. Ed. 46(), 2007

Yakhvarov, Angew. Chem. 118(), 2006

Yakhvarov, Angew. Chem., Int. Ed. 45(), 2006

Stephens, J. Am. Chem. Soc. 127(), 2005

Ahlrichs, Chem. Phys. Lett. 162(), 1989

Gonzalez, J. Chem. Phys. 90(), 1989

Gonzalez, J. Phys. Chem. 94(), 1990

Weigend, Theor. Chim. Acc. 97(), 1997

Foster, J. Am. Chem. Soc. 102(), 1980

Reed, J. Chem. Phys. 78(), 1983

Schaftenaar, J. Comput.-Aided Mol. Des. 14(), 2000
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