An experimental and theoretical study of the basicity of tetra-tert-butyltetrahedrane

Chemistry - A European Journal

Volumn 7, Issue 2, 2001, Pages 342-346

  Notario, Rafael ^d   Castaño, Obis ^b   Andrés, José Luis ^c   Elguero, José ^a   Maier, Günther ^e   Hermann, Christian ^e  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSITY OF ALCALÁ   (Spain)

^c UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^d INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^e JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Ab initio calculations; Basicity; Cyclobutadienes; Strained molecules; Superbases; Tetrahedranes

Indexed keywords

1,3 BUTADIENE; AMMONIA; AMMONIUM DERIVATIVE; BASE; CYCLOBUTADIENE; TETRA TERT BUTYLTETRAHEDRANE; TETRAHEDRANE AMMONIUM COMPLEX; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; CALCULATION; CHEMICAL REACTION; MASS SPECTROMETRY; SYNTHESIS; THEORETICAL STUDY;

EID: 0035910441     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010119)7:2<342::AID-CHEM342>3.0.CO;2-Y     Document Type: Article

References (69)

1. +, protonated tetra-tert-butylcyclobutadiene.
2. Summaries: a) G. Maier, Angew. Chem. 1974, 86, 491-505; Angew. Chem. Int. Ed. Engl. 1974, 13, 425-438;
3. Summaries: a) G. Maier, Angew. Chem. 1974, 86, 491-505; Angew. Chem. Int. Ed. Engl. 1974, 13, 425-438;
4. b) A. Greenberg, J. F. Liebman, Strained Organic Molecules, Academic Press, New York, 1978;
5. c) N. S. Zefirov, A. S. Koz'min, A. V. Abramenkov, Russ. Chem. Rev. (Engl.) 1978, 47, 163-171
6. d) G. Maier, Angew. Chem. 1988, 100, 317-341; Angew. Chem. Int. Ed. Engl. 1988, 27, 309-332;
7. d) G. Maier, Angew. Chem. 1988, 100, 317-341; Angew. Chem. Int. Ed. Engl. 1988, 27, 309-332;
8. e) V. I. Minkin, M. N. Glukhovtsev, B. Ya. Simkin, Aromaticity and Anti-aromaticity: Electronic and Structural Aspects, Wiley, New York, 1994, p. 281.
9. G. Maier, S. Pfriem, U. Schäfer, R. Matusch, Angew. Chem. 1978, 90, 552-553; Angew. Chem. Int. Ed. Engl. 1978, 90, 520-521.
10. G. Maier, S. Pfriem, U. Schäfer, R. Matusch, Angew. Chem. 1978, 90, 552-553; Angew. Chem. Int. Ed. Engl. 1978, 90, 520-521.
11. G. Maier, S. Pfriem, U. Schäfer, K.-D. Malsch, R. Matusch, Chem. Ber. 1981, 114, 3965-3987.
12. G. Maier, S. Pfriem, K.-D. Maisch, H.-O. Kalinowski, K. Dehnicke, Chem. Ber. 1981, 114, 3988-3996.
13. K. B. Wiberg, R. F. W. Bader, C. D. H. Lau, J. Am. Chem. Soc. 1987, 109, 985-1001
14. H. Kollmar, J. Am. Chem. Soc. 1980, 102, 2617-2621.
15. B. A. Hess, L. J. Schaad, J. Am. Chem. Soc. 1985, 107, 865-866.
16. [15]
17. Summary: G. Maier, R. Wolf, F. Fleischer, GIT Fachz. Lab. 1992, 506-511.
18. a) G. Maier, D. Born, Angew. Chem. 1989, 101, 1085-1087; Angew. Chem. Int. Ed. Engl. 1989, 28, 1050-1052;
19. a) G. Maier, D. Born, Angew. Chem. 1989, 101, 1085-1087; Angew. Chem. Int. Ed. Engl. 1989, 28, 1050-1052;
20. b) G. Maier, D. Born, I. Bauer, R. Wolf, R. Boese, D. Cremer, Chem. Ber. 1994, 127, 173-189.
21. a) G. Maier, R. Wolf, H.-O. Kalinowski, Angew. Chem. 1992, 104, 764-766; Angew. Chem. Int. Ed. Engl. 1992, 31, 738-740;
22. a) G. Maier, R. Wolf, H.-O. Kalinowski, Angew. Chem. 1992, 104, 764-766; Angew. Chem. Int. Ed. Engl. 1992, 31, 738-740;
23. b) G. Maier, R. Wolf, H.-O. Kalinowski, R. Boese, Chem. Ber. 1994, 127, 191-200.
24. G. Maier, R. Wolf, H.-O. Kalinowski, Chem. Ber. 1994, 127, 201-207.
25. G. Maier, F. Fleischer, H.-O. Kalinowski, Liebigs Ann. 1995, 173-186.
26. G. Maier, H. Rang, D. Born, Cage Hydrocarbons, Wiley, New York, 1990, 219-259.
27. R. Notario, J. Elguero, J. Chem. Soc. Chem. Commun. 1995, 1543-1544.
28. I. Alkorta, J. Elguero, Tetrahedron 1997, 53, 9741-9748.
29. G. Maier, R. Emrich, K.-D. Malsch, K.-A. Schneider, M. Nixdorf, A. Irngartinger, Chem. Ber. 1985, 118, 2798-2810.
30. Experimental gas-phase basicities for the reference bases were taken from: E. P. L. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data 1998, 27, 413-656.
31. a) M. Decouzon, J.-F. Gal, P.-C. Maria, E. D. Raczynska, Rapid Commun. Mass Spectrom. 1993, 7, 599-602;
32. b) E. D. Raczynska, P.-C. Maria, J.-F. Gal, M. Decouzon, J. Phys. Org. Chem. 1994, 7, 725-733.
33. K. Mislow, W. D. Hounshell, personal communication; ref. [24] in W. T. Borden, E. R. Davidson, Acc. Chem. Res. 1981, 14, 69-76.
34. K. Mislow, W. D. Hounshell, personal communication; ref. [24] in W. T. Borden, E. R. Davidson, Acc. Chem. Res. 1981, 14, 69-76.
35. A. Schweig, W. Thiel, J. Am. Chem. Soc. 1979, 101, 4742-4743.
36. A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502-16513.
37. + (Scheme 1): C1-C4 1.524 vs 1.524 Å, C1-C2 1.826 vs 1.806 Å, C1-C3 1.413 vs 1.408 Å.
38. I. Rozas, I. Alkorta, J. Elguero, J. Phys. Chem. A 1997, 101, 9457-9463; I. Alkorta, I. Rozas, J. Elguero, Chem. Soc. Rev. 1998, 27, 163-170.
39. I. Rozas, I. Alkorta, J. Elguero, J. Phys. Chem. A 1997, 101, 9457-9463; I. Alkorta, I. Rozas, J. Elguero, Chem. Soc. Rev. 1998, 27, 163-170.
40. a) K. Fukui, Acc. Chem. Res., 1981, 14, 363-368;
41. b) C. González, H. B. Schlegel, J. Chem. Phys., 1989, 90, 2154-2161;
42. c) C. González, B. H. Schlegel, J. Phys. Chem., 1990, 94, 5523-5527.
43. a) G. Maier, F. Fleischer, Tetrahedron Lett. 1991, 57-60;
44. b) G. Maier, F. Fleischer, Liebigs Ann. 1995, 169-172.
45. a) Gas-Phase Ion Chemistry, Vols. 1-3 (Ed.: M. T. Bowers), Academic Press, New York, 1979 (Vols. 1 and 2) , 1984 (Vol. 3);
46. a) Gas-Phase Ion Chemistry, Vols. 1-3 (Ed.: M. T. Bowers), Academic Press, New York, 1979 (Vols. 1 and 2) , 1984 (Vol. 3);
47. a) Gas-Phase Ion Chemistry, Vols. 1-3 (Ed.: M. T. Bowers), Academic Press, New York, 1979 (Vols. 1 and 2) , 1984 (Vol. 3);
48. b) "Fourier Transform Mass Spectrometry. Evolution, Innovation and Applications" ACS Symp. Ser. 1987, 359, 1-125;
49. c) A. G. Marshall, F. R. Verdun, Fourier Transforms in NMR, Optical and Mass Spectrometry, Elsevier, Amsterdam, 1990;
50. d) FT-ICR/MS: Analytical Applications of Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (Ed.: B. Asamoto), VCH, Weinheim, 1991;
51. e) A. G. Marshall, C. L. Hendrickson, G. S. Jackson, Mass Spectrom. Rev. 1998, 17, 1-35;
52. f) "Energetics of Stable Molecules and Reactive Intermediates", J.-L. M. Abboud, R. Notario, NATO ASI Ser. Ser. C 1999, 35, 281-302.
53. F. H. Laukien, M. Allemann, P. Bischofberger, P. Grossmann, H. P. Kellerhals, P. Kofel, ACS Symp. Ser. 1987, 359 81-99.
54. a) J.-L. M. Abboud, M. Herreros, R. Notario, M. Essefar, O. Mó, M. Yáñez, J. Am. Chem. Soc. 1996, 118, 1126-1130;
55. b) J.-L. M. Abboud, M. Herreros, R. Notario, O. Mó, M. Yáñez, M. Regitz, J. Elguero, J. Org. Chem. 1996, 61, 7813-7818;
56. c) J.-L. M. Abboud, O. Castaño, J. Elguero, N. Jagerovic, R. Notario, K. Sak, Int. J. Mass Spectrom. Ion Proc. 1998, 175, 35-40.
57. M. Sena, J. M. Riveros, J. Phys. Chem. A 1997, 101, 4348-4391.
58. J. E. Bartmess, R. M. Georgiadis, Vacuum 1983, 33, 149-153.
59. K. J. Miller, J. Am. Chem. Soc. 1990, 112, 8533-8542.
60. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
61. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
62. c) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
63. d) P. J. Stephens, F, J, Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
64. a) W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261.
65. b) M. J. Frisch, J. A. Pople, J. S. Binkley, J. Chem. Phys. 1984, 50, 3265-3269.
66. a) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654;
67. b) T. Clark, J. Chandrasekhar, G. W. Spitznagel, P. v. R. Schleyer, J. Comp. Chem. 1983, 4, 294-301.
68. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andrés, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian98, Gaussian, Pittsburgh PA, 1998.
69. J. A. Pople, M. Head-Gordon, K. Raghavachari, J. Chem. Phys. 1987, 87, 5968-5975.