Molecular mousetraps: Gas-phase studies of the covalent coupling of noncovalent complexes initiated by reactive carbenes formed by controlled activation of diazo precursors

Angewandte Chemie - International Edition

Volumn 42, Issue 9, 2003, Pages 1012-1015

  Julian, Ryan R ^a   May, Jeremy A ^b   Stoltz, Brian M ^b   Beauchamp, J L ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Amino acids; Carbenes; Electrospray ionization; Host guest systems; Molecular recognition

Indexed keywords

CHEMICAL ACTIVATION; CHEMICAL BONDS; DISSOCIATION; PHASE COMPOSITION;

COVALENT COUPLING;

COMPLEXATION;

CARBENOID;

ARTICLE; COVALENT BOND; EXPERIMENT; GAS; PRECURSOR; THEORY;

EID: 0037416334     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390258     Document Type: Article

References (32)

1. M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2494.
2. P. D. Beer, P. A. Gale, D. K. Smith, Supramolecular Chemistry, Oxford University Press, New York, 1999.
3. a) R. R. Julian, J. L. Beauchamp, Int. J. Mass Spectrom. 2001, 210, 613-623;
4. b) R. D. Smith, J. E. Bruce, Q. Y. Wu, Q. P. Lei, Chem. Soc. Rev. 1997, 26, 191-202;
5. c) T. D. Veenstra, Biophys. Chem. 1999, 79, 63-79;
6. d) J. A. Loo, Int. J. Mass Spectrom. 2000, 200, 175-186.
7. +, see for example: R. Flammang, M. T. Nguyen, G. Bouschoux, P. Gerbaux, Int. J. Mass Spectrom. 2002, 202, A8-A25.
8. a) E. M. Marzluff, J. L. Beauchamp in Large Ions: Their Vaporization, Detection, and Structural Analysis; (Eds.: T. Baer, C. Y. Ng, I. Powis), Wiley, New York, 1996, pp. 115-143;
9. b) S. A. McLuckey, J. Am. Soc. Mass Spectrom. 1992, 3, 599-614;
10. c) R. N. Hayes, M. L. Gross, Methods Enzymol. 1990, 193, 237-263.
11. F. O. Rice, A. L. Glasebrook, J. Am. Chem. Soc. 1934, 56, 2381-2383;
12. b) G. Herzberg, Proc. R. Soc. London Ser. A 1961, 262, 291-317; Carbenes, Vols. 1 and 2 (Eds.: R. A. Moss, M. Jones, Jr.), Wiley, New York, 1973, 1975;
13. c) G. Herzberg, Proc. R. Soc. London Ser. A 1961, 262, 291-317; Carbenes, Vols. 1 and 2 (Eds.: R. A. Moss, M. Jones, Jr.), Wiley, New York, 1973, 1975;
14. d) J. D. Rynbrandt, B. S. Rabinovitch, J. Phys. Chem. 1970, 74, 4175-4176;
15. e) J. D. Rynbrandt, B. S. Rabinovitch, J. Chem. Phys. 1971, 54, 2275-2276;
16. f) J. C. Poutsma, J. J. Nash, J. A. Paulino, R. R. Squires, J. Am. Chem. Soc. 1997, 119, 4686-4697;
17. g) J. A. Paulino, R. R. Squires, J. Am. Chem. Soc. 1991, 113, 5573-5580;
18. h) D. G. Leopold, K. K. Murray, A. E. S. Miller, W. C. Lineberger, J. Chem. Phys. 1985, 83, 4849-4865, and references therein;
19. i) R. Bertani, R. A. Michelin, M. Mozzon, P. Traldi, R. Seraglia, L. Busetto, M. C. Cassani, P. Tagleatesta, G. D'Arcangelo, Organometallics 1997, 16, 3229-3233.
20. a) M. P. Doyle, M.A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998;
21. b) C. J. Moody, Whitham, G. H. Reactive Intermediates, Oxford University Press, New York, 1992, pp. 26-50.
22. a) J. S. Bradshaw, R. M. Izatt, A. V. Borkunov, C. Y. Zhu, J. K. Hathaway, Comprehensive Supramolecular Chemistry, Vol. 1 (Ed.: G. W. Gokel), Pergamon/Elsevier, Oxford, 1996, pp. 35-95;
23. b) S. Maleknia, J. Brodbelt, J. Am. Chem. Soc. 1993, 115, 2837-2843;
24. c) D. V. Dearden, C. Dejsupa, Y. Liang, J. S. Bradshaw, R. M. Izatt, J. Am. Chem. Soc. 1997, 119, 353-359;
25. d) C. A. Schalley, Mass Spectrom. Rev. 2001, 20, 253-309;
26. e) J. A. Loo, Int. J. Mass Spectrom. 2000, 200, 175-186.
27. C6 locks protons onto primary amines, see ref. [3a] and: S.-W. Lee, H.-N. Lee, H. S. Kim, J. L. Beauchamp, J. Am. Chem. Soc. 1998, 120, 5800-5805.
28. A Wolff rearrangement is a likely competing reaction for the carbene. See, for example, a) I. Likhotvorik, Z. Zhendong, E. L. Tae, E. Tippmann, B. T. Hill, M. S. Platz, J. Am. Chem. Soc. 2001, 123, 6061-6068;
29. ref. [13]
30. Both results obtained in the current work and in: D. C. Richardson, M. E. Hendrick, M. Jones, J. Am. Chem. Soc. 1971, 93, 3790-3791, where Wolff rearrangement is observed, must proceed through the singlet state.
31. J. R. Pliego, W. B. Almeida, J. Phys. Chem. A 1999, 103, 3904-3909.
32. A. P. Scott, M. S. Platz, L. Radom, J. Am. Chem. Soc. 2001, 123, 6069-6076.