Volume 115, Issue 9 pp. 1074-1076

Zuschrift

Protonation of Cubane in the Gas Phase: A High-Level Ab Initio and DFT Study^†

Correction(s) for this article

José-Luis M. Abboud Prof. Dr.,

José-Luis M. Abboud Prof. Dr.

[email protected]

Instituto de Química Física “Rocasolano”, CSIC, C/Serrano, 119, 28006 Madrid, Spain, Fax: (+34) 91-585-5184

Search for more papers by this author

Ilmar A. Koppel Prof. Dr.,

Ilmar A. Koppel Prof. Dr.

[email protected]

Institute of Chemical Physics, University of Tartu, 2 Jakobi St. 51014 Tartu, Estonia, Fax: (+372) 7-375-264

Search for more papers by this author

Juan Z. Dávalos Dr.,

Juan Z. Dávalos Dr.

Instituto de Química Física “Rocasolano”, CSIC, C/Serrano, 119, 28006 Madrid, Spain, Fax: (+34) 91-585-5184

Search for more papers by this author

Peeter Burk Prof. Dr.,

Peeter Burk Prof. Dr.

Institute of Chemical Physics, University of Tartu, 2 Jakobi St. 51014 Tartu, Estonia, Fax: (+372) 7-375-264

Search for more papers by this author

Ivar Koppel Dr.,

Ivar Koppel Dr.

Institute of Chemical Physics, University of Tartu, 2 Jakobi St. 51014 Tartu, Estonia, Fax: (+372) 7-375-264

Search for more papers by this author

Esther Quintanilla Eng.,

Esther Quintanilla Eng.

Instituto de Química Física “Rocasolano”, CSIC, C/Serrano, 119, 28006 Madrid, Spain, Fax: (+34) 91-585-5184

Search for more papers by this author

José-Luis M. Abboud Prof. Dr.,

José-Luis M. Abboud Prof. Dr.

[email protected]

Instituto de Química Física “Rocasolano”, CSIC, C/Serrano, 119, 28006 Madrid, Spain, Fax: (+34) 91-585-5184

Search for more papers by this author

Ilmar A. Koppel Prof. Dr.,

Ilmar A. Koppel Prof. Dr.

[email protected]

Institute of Chemical Physics, University of Tartu, 2 Jakobi St. 51014 Tartu, Estonia, Fax: (+372) 7-375-264

Search for more papers by this author

Juan Z. Dávalos Dr.,

Juan Z. Dávalos Dr.

Instituto de Química Física “Rocasolano”, CSIC, C/Serrano, 119, 28006 Madrid, Spain, Fax: (+34) 91-585-5184

Search for more papers by this author

Peeter Burk Prof. Dr.,

Peeter Burk Prof. Dr.

Institute of Chemical Physics, University of Tartu, 2 Jakobi St. 51014 Tartu, Estonia, Fax: (+372) 7-375-264

Search for more papers by this author

Ivar Koppel Dr.,

Ivar Koppel Dr.

Institute of Chemical Physics, University of Tartu, 2 Jakobi St. 51014 Tartu, Estonia, Fax: (+372) 7-375-264

Search for more papers by this author

Esther Quintanilla Eng.,

Esther Quintanilla Eng.

Instituto de Química Física “Rocasolano”, CSIC, C/Serrano, 119, 28006 Madrid, Spain, Fax: (+34) 91-585-5184

Search for more papers by this author

First published: 26 February 2003

https://doi.org/10.1002/ange.200390244

Citations: 6

^†

This work was supported by grants BQU2000-1497 (Spanish DGES) and 5226 (Estonian Science Foundation) and by a Joint Project CSIC–Estonian Academy of Sciences “The Reactivity of the Strained Cage Molecules”.

Share a link

Email
Wechat
Bluesky

Graphical Abstract

Das Tetracyclo[4.2.0.0^2,4.0^3,8]oct-7-ylium-Kation ist Ab-initio-Rechnungen zufolge das Produkt der Gasphasenprotonierung von Cuban (1). Auf dem G2(MP2)-Niveau ist die berechnete Gasphasenbasizität von 1 um ca. 60 kcal mol⁻¹ größer als die experimentell bestimmte. Die experimentellen thermodynamischen Daten sind in Einklang mit einer schnellen Deprotonierung von 2 unter Bildung von Cunean (3).

Supporting Information

References

1
1aPentacyclo[4.2.0^2,5.0^3,8.0^4,7]octane.
Google Scholar
1bP. E. Eaton, T. W. Cole, Jr., J. Am. Chem. Soc. 1964, 86, 962–964;
10.1021/ja01059a072
CAS Web of Science® Google Scholar
1cP. E. Eaton, Angew. Chem. 1992, 104, 1447–1462;
10.1002/ange.19921041105
CAS Google Scholar
Angew. Chem. Int. Ed. Engl. 1992, 31, 1421–1436;
10.1002/anie.199214211
Web of Science® Google Scholar
1dT. Yildirim, P. M. Gehring, D. A. Neumann, P. E. Eaton, T. Emrick, Carbon 1998, 36, 809–815.
10.1016/S0008-6223(98)00009-8
CAS Web of Science® Google Scholar
2I. Santos, D. W. Balogh, C. W. Doecke, A. G. Marshall, L. A. Paquette, J. Am. Chem. Soc. 1986, 108, 8183–8185.
10.1021/ja00286a011
CAS Web of Science® Google Scholar
3E. P. L. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data 1998, 27, 413–656.
10.1063/1.556018
CAS Web of Science® Google Scholar
4Full computational details are given in the Supporting Information.
Google Scholar
5There is also an isomer in which the proton is located at the center of the cube (O_h symmetry). At the B3LYP/6-311+G(d,p) level, this endohedral structure, 1H, is 199.7 kcal mol⁻¹ less stable than 1H and is not a minimum on the potential energy surface of 1H⁺ (see Supporting Information).
Google Scholar
6P. Politzer, L. N. Domelsmith, L. Abrahmsen, J. Phys. Chem. A 1984, 88, 1752–1758.
10.1021/j150653a018
CAS Web of Science® Google Scholar
7
7aA. D. Becke, J. Chem. Phys. 1993, 98, 5648–5652;
10.1063/1.464913
CAS Web of Science® Google Scholar
7bC. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785–789;
10.1103/PhysRevB.37.785
CAS PubMed Web of Science® Google Scholar
7cS. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200–1211;
10.1139/p80-159
CAS Web of Science® Google Scholar
7dP. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11 623–11 627.
10.1021/j100096a001
CAS Web of Science® Google Scholar
8W. J. Hehre, L. Radom, P. von R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
10.1021/ja00267a063
CAS Google Scholar
9J. B. Foresman, Æ. Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed., Gaussian Inc., Pittsburgh, 1996.
Google Scholar
10H. Jiao, P. von R. Schleyer, J. Am. Chem. Soc. 1995, 117, 11 529–11 535.
10.1021/ja00151a017
CAS Web of Science® Google Scholar
11L. A. Curtiss, K. Raghavachari, J. A. Pople, J. Chem. Phys. 1993, 98, 1293–1298.
10.1063/1.464297
CAS Web of Science® Google Scholar
12For example, see D. W. Rogers, J. Mol. Struct. 2000, 556, 207–215, and references therein.
10.1016/S0022-2860(00)00634-7
CAS Web of Science® Google Scholar
13
13aPentacyclo[3.3.0.0^2,4.0^3,7.0^6,8]octane.
Google Scholar
13bL. Cassar, P. E. Eaton, J. Halpern, J. Am. Chem. Soc. 1970, 92, 6366–6368.
10.1021/ja00714a075
CAS Web of Science® Google Scholar
14
14aJ.-L. M. Abboud, O. Castaño, J. Z. Dávalos, P. Jiménez, R. Gomperts, P. Müller, M. V. Roux, J. Org. Chem. 2002, 67, 1057–1060;
10.1021/jo016206f
CAS PubMed Web of Science® Google Scholar
14bJ.-L. M. Abboud, O. Castaño, J. Z. Dávalos, R. Gomperts, Chem. Phys. Lett. 2001, 337, 327–330.
10.1016/S0009-2614(01)00212-3
CAS Web of Science® Google Scholar
15R. Wolfshütz, H. Schwarz, Int. J. Mass Spectrom. Ion Phys. 1980, 33, 291–297.
10.1016/0020-7381(80)85008-X
Web of Science® Google Scholar
16S. Moss, B. T. King, A. de Meijere, S. I. Kozhushkov, P. E. Eaton, J. Michl, Org. Lett. 2001, 3, 2375–2377.
10.1021/ol0161864
CAS PubMed Web of Science® Google Scholar

Citing Literature

Volume115, Issue9

March 3, 2003

Pages 1074-1076

This is the

German version

of Angewandte Chemie.

Note for articles published since 1962:

Do not cite this version alone.

Take me to the International Edition version with citable page numbers, DOI, and citation export.

We apologize for the inconvenience.

Protonation of Cubane in the Gas Phase: A High-Level Ab Initio and DFT Study^†

Correction(s) for this article

A Spiro-Fused Triarylaminium Radical Cation with a Triplet Ground State

Graphical Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Protonation of Cubane in the Gas Phase: A High-Level Ab Initio and DFT Study†

Correction(s) for this article

A Spiro-Fused Triarylaminium Radical Cation with a Triplet Ground State

Graphical Abstract

Supporting Information

References

Citing Literature

References

Related

Information

Protonation of Cubane in the Gas Phase: A High-Level Ab Initio and DFT Study^†