Spectroscopic Identification of Oxonium and Carbenium Ions of Protonated Phenol in the Gas Phase: IR Spectra of Weakly Bound C6H 7O+-L Dimers (L = Ne, Ar, N2)

Journal of the American Chemical Society

Volumn 126, Issue 6, 2004, Pages 1716-1725

  Solcà, Nicola ^a   Dopfer, Otto ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; INFRARED SPECTROSCOPY; IONS; ISOMERS; PHOTODISSOCIATION; SUBSTITUTION REACTIONS;

ELECTROPHILICITY; PROTONATION;

PHENOLS;

ARGON; AROMATIC COMPOUND; CARBENE; CARBENIUM ION; CARBON; DIMER; HYDROXYL GROUP; ION; LIGAND; NEON; NITROGEN; OXONIUM ION; OXYGEN; PHENOL; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DISSOCIATION; GAS; HYDROGEN BOND; INFRARED SPECTROSCOPY; ISOMER; PROTON TRANSPORT; QUANTUM CHEMISTRY; SOLVATION; SUBSTITUTION REACTION; VIBRATION;

EID: 1242291812     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0305858     Document Type: Article

References (67)

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Wiley: New York, 1992.
2. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry; Plenum Press: New York, 1993.
3. Ohtaki, H.; Radnai, T. Chem. Rev. 1993, 93, 1157.
4. Lenoir, D. Angew. Chem., Int. Ed. 2003, 42, 854.
5. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Systems; Springer: Heidelberg, 1991.
6. Perkampus, H. H.; Baumgarten, E. Angew. Chem., Int. Ed. Engl. 1964, 3, 776.
7. Brouwer, D. M.; Mackor, E. L.; MacLean, C. Arenonium Ions. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York, 1970; Vol. II.
8. Dewey, T. X.; Barich, H.; Torres, P. D.: Haw, J. F. J. Am. Chem. Soc. 1997, 119, 406.
9. Hubig, S. M.; Kochi, J. K. J. Org. Chem. 2000, 65, 6807.
10. Reed, C. A.; Kim, K. C.; Stoyanov, E. S.; Stasko, D.; Tham, F. S.; Mueller, L. J.; Boyd, P. D. W. J. Am. Chem. Soc. 2003, 125, 1796.
11. Esteves, P. M.; de M. Carneiro, J. W.; Cardoso, S. P.; Barbosa, A. G. H. ; Laali, K. K.; Rasul, G.; Prakash, G. K. S.; Olah, G. A. J. Am. Chem. Soc. 2003, 125, 4836.
12. Olah, G. A.; Mo, Y. K. J. Org. Chem. 1973, 38, 3.
13. Weinkauf, R.; Schermann, J. P.; de Vries, M. S.; Kleinermanns, K. Eur. Phys. J. D. 2002, 20, 309.
14. Speranza, M. Mass Spectrom. Rev. 1992, 73.
15. Kuck, D. Mass Spectrom. Rev. 1990, 583.
16. Fornarini, S. Mass Spectrom. Rev. 1997, 365.
17. Fornarini, S.; Crestoni, M. E. Acc. Chem. Res. 1998, 31, 827.
18. Freiser, B. S.; Beauchamp, J. L. J. Am. Chem. Soc. 1976, 98, 3136.
19. Freiser, B. S.; Beauchamp, J. L. J. Am. Chem. Soc. 1977, 99, 3214.
20. Solcà, N.; Dopfer, O. Angew. Chem., Int. Ed. 2002, 41, 3628.
21. Solcà, N.; Dopfer, O. Chem.-Eur. J. 2003, 9, 3154.
22. Jones, W.; Boissel, P.; Chiavarino, B.; Crestoni, M. E.; Fornarini, S.; Lemaire, J.; Maitre, P. Angew. Chem., Int. Ed. 2003, 42, 2057.
23. Solcà, N.; Dopfer, O. Chem. Phys. Lett. 2001, 342, 191.
24. Solcà, N.; Dopfer, O. J. Am. Chem. Soc. 2003, 125, 1421.
25. Solcà, N.; Dopfer, O. Angew. Chem., Int. Ed. 2003, 42, 1537.
26. Bieske, E. J.; Dopfer, O. Chem. Rev. 2000, 100, 3963.
27. Yeh, L. I.; Okumura, M.; Myers, J. D.; Price, J. M.; Lee, Y. T. J. Chem. Phys. 1989, 91, 7319.
28. Nizkorodov, S. A.; Roth, D.; Olkhov, R. V.; Maier, J. P.; Dopfer, O. Chem. Phys. Lett. 1997, 278, 26-30.
29. Olkhov, R. V.; Dopfer, O. Chem. Phys. Lett. 1999, 314, 215.
30. Solcà, N.; Dopfer, O. J. Phys. Chem. A 2001, 105, 5637.
31. Eckert-Maksic, M.; Klessinger, M.; Maksic, Z. B. Chem. Phys. Lett. 1995, 232, 472.
32. Tishchenko, O.; Pham-Tran, N. N.; Kryachko, E. S.; Nguyen, M. T. J. Phys. Chem. A 2001, 105, 8709.
33. Bouchoux, G.; Defaye, D.; McMahon, T.; Likholyot, A.; Mo, O.; Yanez, M. Chem.-Eur. J. 2002, 8, 2900.
34. Heidrich, D. Angew. Chem., Int. Ed. 2002, 41, 3208.
35. Lau, Y. K.; Kebarle, P. J. Am. Chem. Soc. 1976, 98, 7452.
36. DeFrees, D. J.; McIver, R. T.; Hehre, W. J. J. Am. Chem. Soc. 1977, 99, 3853.
37. Martinsen, D. P.; Buttril, S. E., Jr. Org. Mass. Spectrom. 1976, 11, 762.
38. Martinsen, D. P.; Buttril, S. E., Jr. J. Am. Chem. Soc. 1978, 100, 6559.
39. Wood, K. V.; Burinsky, D. J.; Cameron, D.; Cooks, R. G. J. Org. Chem. 1983, 48, 5236.
40. Dopfer, O. Int. Rev. Phys. Chem. 2003, 22, 437.
41. Guelachvili, G.; Rao, K. N. Handbook of Infrared Standards; Academic Press: London, 1993.
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
43. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
44. Chalasinski, G.; Szczesniak, M. M. Chem. Rev. 1994, 94, 1.
45. Hunter, E. P. L.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
46. +-Ne dimers are not discussed further.
47. Solcà, N.; Dopfer, O. J. Mol. Struct. 2001, 563-564, 241.
48. Solcà, N.: Dopfer, O. Chem. Phys. Lett. 2000, 325, 354.
49. Solcà, N.; Dopfer, O. Chem. Phys. Lett. 2003, 369, 68.
50. Multiphoton absorptions can be excluded at the low laser intensities available (eq 6).24.51
51. Solcà, N.; Dopfer, O. Chem. Phys. Lett. 2001, 347, 59.
52. Solcà, N. Ph.D. Thesis, University of Basel, 2003.
53. 0 (see text).
54. -1) complexes.
55. Solcà, N.; Dopfer, O. J. Phys. Chem. A 2002, 106, 7261.
56. Solcà, N.; Dopfer, O. Eur. Phys. J. D 2002, 20, 469.
57. Roth, D.; Dopfer, O.; Maier, J. P. Phys. Chem. Chem. Phys. 2001, 3, 2400.
58. Dopfer, O.; Roth, D.; Maier, J. P. J. Chem. Phys. 2001, 114, 7081.
59. Roth, D.; Dopfer, O.; Maier, J. P. Phys. Chem. Chem. Phys. 2000, 2, 5013.
60. Dopfer, O.; Nizkorodov, S. A.; Olkhov, R. V.; Maier, J. P.; Harada, K. J. Phys. Chem. A 1998, 102, 10017.
61. Dopfer, O.; Roth, D.; Maier, J. P. J. Chem. Phys. 2000, 113, 120.
62. 2 group, with barriers of 2.5 (B3LYP) and 5.7 (MP2) kJ/mol, possibly causes further shifts and splittings. No evidence for this splitting is observed in the dimer spectra.
63. Bist, H. D.; Brand, J. C. D.; Williams, D. R. J. Mol. Spectrosc. 1967, 24, 402.
64. Kim, H.; Green, R. J.; Qian, J.; Anderson, S. L. J. Chem. Phys. 2000, 112, 5717.
65. Bader, R. F. W.; Chang, C. J. Phys. Chem. 1989, 93, 5095.
66. Dopfer, O. J. Phys. Chem. A 2000, 104, 11693.
67. Sheng, Y.; Leszcynski, J. Collect. Czech. Chem. Commun. 2003, 68, 489.