Gas-phase fragmentation of deprotonated p-hydroxyphenacyl derivatives

Journal of Organic Chemistry

Volumn 76, Issue 7, 2011, Pages 2180-2186

  Remeš, Marek ^a,b   Roithová, Jana ^a   Schröder, Detlef ^b   Cope, Elizabeth D ^c   Perera, Chamani ^c   Senadheera, Sanjeewa N ^c   Stensrud, Kenneth ^c   Ma, Chi Cheng ^c   Givens, Richard S ^c  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLLISIONAL ACTIVATION; CONJUGATE ACID; DEPROTONATED SPECIES; DIRADICALS; ENERGY DEMANDS; GAS-PHASE ACIDITIES; GAS-PHASE FRAGMENTATION; GASPHASE; LEAVING GROUPS; METHANOLIC SOLUTION; THEORETICAL STUDY;

ELECTROSPRAY IONIZATION; GASES; IONS;

IONIZATION OF GASES;

4 HYDROXYPHENACYL DERIVATIVE; ACETONE; EPOXIDE; PHENACYL CHLORIDE; PHENOL DERIVATIVE; SPIROCYCLOPROPANONE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; CONJUGATION; ELECTROSPRAY; ENERGY; FRAGMENTATION REACTION; GAS PHASE FRAGMENTATION; SIGNAL TRANSDUCTION;

ACETOPHENONES; ANIONS; CYCLOPROPANES; EPOXY COMPOUNDS; MODELS, THEORETICAL; MOLECULAR STRUCTURE; NOBLE GASES; SOLUTIONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPIRO COMPOUNDS;

EID: 79953224454     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1025223     Document Type: Article

References (79)

1. Conrad, P. G.; Givens, R. S.; Hellrung, B.; Rajesh, C. S.; Ramseier, M.; Wirz, J. J. Am. Chem. Soc. 2000, 122, 9346
2. Givens, R. S.; Heger, D.; Hellrung, B.; Kamdzhilov, Y.; Mac, M.; Conrad, P. G.; Cope, E.; Lee, J. I.; Mata-Segreda, J. F.; Schowen, R. L.; Wirz, J. J. Am. Chem. Soc. 2008, 130, 3307
3. Stensrud, K. F.; Heger, D.; Šebej, P.; Wirz, J.; Givens, R. S. Photochem. Photobiol. Sci. 2008, 7, 614
4. Stensrud, K.; Noh, J.; Kandler, K.; Wirz, J.; Heger, D.; Givens, R. S. J. Org. Chem. 2009, 74, 5219 See also: Park, C. H.; Givens, R. S. J. Am. Chem. Soc. 1997, 119, 2453
5. Givens, R. S.; Goeldner, M., Eds. Dynamic Studies in Biology: Phototriggers, Photoswitches, and Caged Biomolecules; Wiley: New York, 2005.
6. Givens, R. S.; Weber, J. J. F.; Jung, A. H.; Park, C.-H. In Methods in Enzymology on "Caged Compounds: Chemistry, Instrumentation, and Applications; Marriott, G., Ed.; Academic Press: San Diego, CA, 1998; Vol. 1, 291.
7. Ma, C. S.; Chan, W. S.; Kwok, W. M.; Yuo, P.; Phillips, D. L. J. Phys. Chem. B 2004, 108, 9264
8. Ma, C. S.; Zuo, P.; Kwok, W. M.; Chan, W. S.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Org. Chem. 2004, 69, 6641
9. Ma, C. S.; Kwok, W. M.; Chan, W. S.; Zuo, P.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Am. Chem. Soc. 2005, 127, 1463
10. Zuo, P.; Ma, C. S.; Kwok, W. M.; Chan, W. S.; Phillips, D. L. J. Org. Chem. 2005, 70, 8661
11. Ma, C. S.; Kwok, W. M.; Chan, W. S.; Du, Y.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. J. Am. Chem. Soc. 2006, 128, 2558
12. Chen, X.-B.; Ma, C. S.; Kwok, W. M.; Guan, X.-G.; Du, Y.; Phillips, D. L. J. Phys. Chem. A 2006, 110, 12406
13. Wirz, J. Chimia 2007, 61, 638
14. Chen, X.-B.; Ma, C. S.; Kwok, W. M.; Guan, X.-G.; Du, Y.; Phillips, D. L. J. Phys. Chem. B 2007, 111, 11832
15. Ma, C. S.; Kwok, W. M.; Chan, W. S.; Du, Y.; Zuo, P.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. Curr. Sci. 2009, 97, 202
16. Cao, Q.; Guan, X.; George, M. W.; Phillips, D. L.; Ma, C. S.; Kwok, W. M.; Li, M. D.; Du, Y.; Sun, X.-Z.; Xue, J. D. Faraday Discuss. 2010, 145, 171
17. Zabadal, M.; Pelliccioli, A. P.; Klan, P.; Wirz, J. J. Phys. Chem. A 2001, 105, 10329
18. Klan, P.; Pelliccioli, A. P.; Pospisil, T.; Wirz, J. Photochem. Photobiol. Sci. 2002, 1, 920 See also: Zhang, K.; Corrie, J. E. T.; Munasinghe, V. R. N.; Wan, P. J. Am. Chem. Soc. 1999, 121, 5625
19. Bucher, G.; Phillips, D. L.; Schröder, D.; Carpenter, B.; Guthrie, J. P.; Shaik, S.; Tahara, T.; Warshel, A.; Michl, J.; Williams, I.; Ashfold, M. N. R.; Pandey, R.; Meech, S. R.; Misra, R.; Henchman, R. H.; Hutchings, G. J.; Buurma, N. J.; Bain, C. D.; Glowacki, D.; George, M. W.; Pantos, G. D.; Cramer, C. J.; Lloyd-Jones, G. C.; Hunter, C. A.; Varley, L. M.; Hillman, A. R.; Webb, S.; Philp, D.; Page, M. I. Faraday Discuss. 2010, 145, 255
20. For previous work on Favorskii-type rearrangements in the gas phase, see: Dua, S.; Pollnitz, A. P.; Bowie, J. H. J. Chem. Soc., Perkin Trans. 2 1993, 2235 See also: Han, I. S.; Kim, C. K.; Kim, C. K.; Lee, B. S.; Lee, I. J. Comput. Chem. 1997, 18, 1773
21. For review of anion rearrangements in the gas phase, see: Eichinger, P. C. H.; Dua, S.; Bowie, J. H. Int. J. Mass Spectrom. Ion Processes 1993, 133, 1
22. Ahmad, M. R.; Kass, S. R. Aust. J. Chem. 2003, 56, 453
23. Alcami, M.; Mó, O.; Yañez, M. Mass Spectrom. Rev. 2001, 20, 195
24. Schwarz, H. Int. J. Mass Spectrom. 2004, 237, 75
25. Roithová, J.; Schröder, D. Coord. Chem. Rev. 2009, 253, 666
26. Roithová, J.; Schröder, D. Chem. Rev. 2010, 110, 1170
27. For a promising example toward UV photochemistry in the gas phase, see: Scuderi, D.; Maitre, P.; Rondino, F.; Le Barbu-Debus, K.; Lepere, V.; Zehnacker-Rentien, A. J. Phys. Chem. A 2010, 114, 3306
28. Neutralization-reionization mass spectrometry has been used to characterize the neutral products of ion/molecule reactions in the gas phase, see: Schröder, D.; Sülzle, D.; Hrušák, J.; Böhme, D. K.; Schwarz, H. Int. J. Mass Spectrom. Ion Processes 1991, 110, 145
29. Schröder, D.; Schwarz, H. Helv. Chim. Acta 1992, 75, 1281
30. Schröder, D.; Müller, J.; Schwarz, H. Organometallics 1993, 12, 1972
31. Schröder, D.; Schwarz, H.; Polarz, S.; Driess, M. Phys. Chem. Chem. Phys. 2005, 7, 1049
32. See also: (e) Li, S. H.; Mirabal, A.; Demuth, J.; Wöste, L.; Siebert, T. J. Am. Chem. Soc. 2008, 130, 16832
33. For a neutralization-reionization study of the related acetolactone, see: Schröder, D.; Goldberg, N.; Zummack, W.; Schwarz, H.; Poutsma, J. C.; Squires, R. R. Int. J. Mass Spectrom. Ion Processes 1997, 165/166, 71
34. Roithová, J.; Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. 2005, 44, 3092
35. Roithová, J.; Schröder, D. Int. J. Mass Spectrom. 2007, 267, 134
36. Milko, P.; Roithová, J.; Schröder, D.; Lemaire, J.; Schwarz, H.; Holthausen, M. C. Chem.-Eur. J. 2008, 14, 4318
37. Milko, P.; Roithová, J.; Tsierkezos, N. G.; Schröder, D. J. Am. Chem. Soc. 2008, 130, 7186
38. 3COO in Table 1), but the abundance was much less than a percent of the other fragments and no quantitative analysis of the energy dependence was possible.
39. •) often invoked in photolysis.
40. Šrogl, J.; Hyvl, J.; Révész, A.; Schröder, D. Chem. Commun. 2009, 3463
41. Tsierkezos, N. G.; Buchta, M.; Holý, P.; Schröder, D. Rapid Commun. Mass Spectrom. 2009, 23, 1550
42. Schröder, D.; Ducháčková, L.; Jušinski, I.; Eckert-Maksić, M.; Heyda, J.; Tůma, L.; Jungwirth, P. Chem. Phys. Lett. 2010, 490, 14
43. Révész, A.; Milko, P.; Žabka, J.; Schröder, D.; Roithová, J. J. Mass Spectrom. 2010, 45, 1246
44. Zins, E.-L.; Pepe, C.; Schröder, D. J. Mass Spectrom. 2010, 45, 1253
45. Schröder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2001, 33, 139
46. Schwarz, H. Int. J. Mass Spectrom. 2004, 237, 75
47. Harvey, J. N.; Poli, R.; Smith, K. M. Coord. Chem. Rev. 2003, 238, 347
48. Shaik, S.; Hirao, H.; Kumar, D. Acc. Chem. Res. 2007, 40, 532 See also: Yarkony, D. R. J. Phys. Chem. 1996, 100, 18612
49. Aschi, M.; Harvey, J. N.; Schalley, C. A.; Schröder, D.; Schwarz, H. J. Chem. Soc., Chem. Commun. 1998, 531
50. Schröder, D.; Heinemann, C.; Schwarz, H.; Harvey, J. N.; Dua, S.; Blanksby, S. J.; Bowie, J. H. Chem.-Eur. J. 1998, 4, 2550
51. Roithová, J.; Ricketts, C. L.; Schröder, D.; Price, S. D. Angew. Chem., Int. Ed. 2007, 46, 9316
52. Feixas, F.; Ponec, R.; Schröder, D.; Roithová, J.; Fišer, J.; Price, S. D. J. Phys. Chem. A 2010, 114, 6681
53. For selected other examples of two-state scenarios with only second row elements, see: Janaway, G. A.; Zhong, M. L.; Gatev, G. G.; Chabinyc, M. L.; Brauman, J. I. J. Am. Chem. Soc. 1997, 119, 11697
54. Hu, J.; Hill, B. T.; Squires, R. R. J. Am. Chem. Soc. 1997, 119, 11699
55. Yarkony, D. R. J. Phys. Chem. A 1998, 102, 5305
56. Cui, Q.; Morokuma, K.; Bowman, J. M.; Klippenstein, S. J. J. Chem. Phys. 1999, 110, 9469
57. Griesbeck, A.; Abe, M.; Bondock, S. Acc. Chem. Res. 2004, 37, 919
58. Contreras, R.; Galvan, M.; Oliva, M.; Safont, V. S.; Andres, J.; Guerra, D.; Aizman, A. Chem. Phys. Lett. 2008, 457, 216
59. For solvent effects on the spin inversion of carbenes, see: Hess, G. C.; Kohler, B.; Likhotvorik, I.; Peon, J.; Platz, M. S. J. Am. Chem. Soc. 2000, 122, 8087
60. Wang, J.; Kubicki, J.; Peng, H.; Platz, M. S. J. Am. Chem. Soc. 2008, 130, 6604
61. Givens, R. S.; Stensrud, K.; Conrad, P. G., II; Yousef, A. L.; Perera, C.; Senadheera, S. N.; Heger, D.; Wirz, J. Can. J. Chem. 2011, in press.
62. Tintaru, A.; Roithová, J.; Schröder, D.; Charles, L.; Jušinski, I.; Glasovac, Z.; Eckert-Maksić, M. J. Phys. Chem. A 2008, 112, 12097
63. Cech, N. B.; Enke, C. G. Mass Spectrom. Rev. 2001, 20, 362
64. Schröder, D.; Weiske, T.; Schwarz, H. Int. J. Mass Spectrom. 2002, 219, 729
65. Trage, C.; Diefenbach, M.; Schröder, D.; Schwarz, H. Chem.-Eur. J. 2006, 12, 2454
66. O'Hair, R. A. J. Chem. Commun. 2006, 1469
67. Armentrout, P. B. Int. J. Mass Spectrom. 2000, 200, 219
68. Ervin, K. M. Chem. Rev. 2001, 101, 391
69. Narancic, S.; Bach, A.; Chen, P. J. Phys. Chem. A 2007, 111, 7006
70. Armentrout, P. B.; Ervin, K. M.; Rodgers, M. T. J. Phys. Chem. A 2008, 112, 10071
71. O'Hair, R. A. J.; Vrkic, A. K.; James, P. F. J. Am. Chem. Soc. 2004, 126, 12173
72. Rodgers, M. T.; Stanley, J. R.; Amunugama, R. J. Am. Chem. Soc. 2000, 122, 10969
73. Rannulu, N. S.; Rodgers, M. T. J. Phys. Chem. A 2007, 111, 3465
74. Than, S.; Maeda, H.; Irie, M.; Itoh, S.; Kikukawa, K.; Mishima, K. J. Phys. Chem. A 2007, 111, 5988
75. Schröder, D.; Engeser, M.; Brönstrup, M.; Daniel, C.; Spandl, J.; Hartl, H. Int. J. Mass Spectrom. 2003, 228, 743
76. Jagoda-Cwiklik, B.; Jungwirth, J.; Rulíšek, L.; Milko, P.; Roithová, J.; Lemaire, J.; Maitre, P.; Ortega, J. M.; Schröder, D. ChemPhysChem 2007, 8, 1629
77. Tyo, E. C.; Castleman, A. W., Jr.; Schröder, D.; Milko, P.; Roithová, J.; Ortega, J. M.; Cinellu, M. A.; Cocco, F.; Minghetti, G. J. Am. Chem. Soc. 2009, 131, 13009
78. Gaussian 03, Revision E.01; Gaussian, Inc., Wallingford, CT, 2004.
79. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007