Decomposition of neutral, singly and doubly protonated benzoquinone in the gas phase

Chemistry - A European Journal

Volumn 11, Issue 2, 2005, Pages 628-638

  Roithová, Jana ^a,b   Schröder, Detlef ^a   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

Density functional calculations; Dications electron deficient compounds; Protonation; Quinones

Indexed keywords

CARBON MONOXIDE; DECOMPOSITION; MASS SPECTROMETRY; PROTONS; REACTION KINETICS;

BENZOQUINONE; FRAGMENTATION PATHWAYS; PROTONATION; REACTION MECHANISM;

GASES;

BENZOQUINONE DERIVATIVE; CARBON MONOXIDE; CYCLOPENTANE DERIVATIVE;

ARTICLE; CARBONYLATION; DECOMPOSITION; GAS; MOLECULAR DYNAMICS; PROTON TRANSPORT;

ALGORITHMS; BENZOQUINONES; CARBON MONOXIDE; COMPUTER SIMULATION; INDICATORS AND REAGENTS; MASS SPECTROMETRY; MODELS, CHEMICAL; PROTONS; WATER;

EID: 12444343178     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400738     Document Type: Article

References (47)

1. D. Voet, J. G. Voet, Biochemistry, 2nd ed., Wiley, New York, 1995.
2. E. P. L. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data 1998, 27, 413-656; see also ref. [4], where PA(para-BQ) = 8.31 eV.
3. S. Patai, Z. Rappoport, The Chemistry of Quinoid Compounds, Vol. II, Parts 1 and 2, Wiley, Chichester, 1988.
4. K. K. Irikura, M. Meot-Ner (Mautner), L. W. Sieck, A. D. Fant, J. F. Liebman, J. Org. Chem. 1996, 61, 3167-3171.
5. R. C. Fort, Jr., S. J. Getty, D. A. Hrovat, P. M. Lahti, W. T. Borden, J. Am. Chem. Soc. 1992, 114, 7549-7552.
6. S. G. Lias, "Ionization Energy Evaluation" in NIST Chemistry Web-Book, NIST Standard Reference Database Number 69 (Eds.: P. J. Linstrom, W. G. Mallard), March 2003, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.-gov).
7. M. W. Chase, Jr., J. Phys. Chem. Ref. Data 1998, 9, 1-1951.
8. A. Wassermann, J. Chem. Soc. 1935, 828-838.
9. R. Sabbah, E. N. L. E. Buluku, Can. J. Chem. 1991, 69, 481-488.
10. Note the geometrical similarity with protonated acetone for which the C-O bond length amounts to 1.26 Å.
11. 2 state should be taken with precaution because the description of an open-shell singlet state with single reference methods like UB3LYP inevitably encounters spin-contamination by the triplet state.
12. [5] who used the UHF/6-31G* method for the optimization of the geometry, is a second-order saddle point at the UB 3LYP/cc-pVTZ level of theory.
13. P. Frank, J. Herzler, T. Just, C. Wahl, Twenty-Fifth Symposium (Int.) on Combustion, The Combustion Institute, Pittsburgh, Pennsylvania, 1994, 833-840.
14. M. U. Alzueta, M. Oliva, P. Glarborg, Int. J. Chem. Kinet. 1998, 30, 683-697.
15. W. H. Starnes, Jr., D. A. Plank, J. C. Floyd, J. Org. Chem. 1975, 40, 1124-1127.
16. + are formed in a 1:1 ratio, the lighter fragment ion suffers from significant discrimination effects in detection due to the kinetic energy release in Coulomb explosion; see also: B. A. Rumpf, C. E. Allison, P. J. Derrick, Org. Mass Spectrom. 1986, 21, 295-299.
17. D. Mathur, Phys. Rep. 1993, 225, 193.
18. D. Schröder, H. Schwarz, J. Phys. Chem. A 1999, 103, 7385-7394.
19. W. J. Bouma, P. C. Burgers, J. L. Holmes, L. Radom, J. Am. Chem. Soc. 1986, 108, 1767-1770.
20. P. C. Burgers, J. L. Holmes, A. A. Mommers, J. Am. Chem. Soc. 1985, 107, 1099-1101.
21. D. Kuck, Int. J. Mass Spectrom. 2002, 213, 101-144.
22. H. Schwarz, Top. Curr. Chem. 1981, 97, 1-31.
23. A. J. Illies, M. F. Jarrold, M. T. Bowers, J. Am. Chem. Soc. 1983, 105, 2562-2565.
24. M. Gerhards, C. Unterberg, S. Schumm, J. Chem. Phys. 1999, 111, 7966-7975.
25. H. Schwarz, Top. Curr. Chem. 1978, 73, 231-263.
26. 2+ was checked by re-optimization and frequency calculation at the MP2/6-311G** level.
27. a) M. J. S. Dewar, M. K. Holloway, J. Am. Chem. Soc. 1984, 106, 6619-6627;
28. b) H. Schwarz, Angew. Chem. 1981, 93, 1046-1059; Angew. Chem. Int. Ed. Engl. 1981, 20, 991-1003.
29. b) H. Schwarz, Angew. Chem. 1981, 93, 1046-1059; Angew. Chem. Int. Ed. Engl. 1981, 20, 991-1003.
30. K. Krogh-Jespersen, J. Am. Chem. Soc. 1991, 113, 417-423.
31. 2+. 1,2-Hydrogen shifts are not further considered because it would lead to the scrambling of hydrogen, which was not observed experimentally.
32. We did not attempt to localize transition structures tor the eliminations of the neutral molecules. Generally, the dominant interactions are described by the attractive potentials between the dication and the neutral molecule that finally leads to either barrierless dissociation in excess of the endothermicity or to a very loose transition structure typical for a continuously endothermic dissociation process.
33. J. N. Harvey, M. Aschi, H. Schwarz, W. Koch, Theor. Chem. Acc. 1998, 99, 95-99.
34. M. Aschi, J. N. Harvey, J. Chem. Soc. Perkin Trans. 1 1999, 2, 1059-1062.
35. H. Schwarz, Int. J. Mass Spectrom., and references therein, in press.
36. R. Srinivas, D. Sülzle, T. Weiske, H. Schwarz, Int. J. Mass Spectrom., Ion Proc. 1991, 107, 369-376.
37. J. Roithová, D. Schröder, J. Loos, H. Schwarz, H.-C. Jankowiak, R. Berger, R. Thissen, O. Dutuit unpublished results.
38. K. Lammertsma, P. von R. Schleyer, H. Schwarz, Angew. Chem. 1989, 101, 1313-1335; Angew . Chem. Int. Ed. Engl. 1989, 28, 1321-1341.
39. K. Lammertsma, P. von R. Schleyer, H. Schwarz, Angew. Chem. 1989, 101, 1313-1335; Angew . Chem. Int. Ed. Engl. 1989, 28, 1321-1341.
40. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
41. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
42. c) B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200-206;
43. d) S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200-1211.
44. R. A. Kendall, T. H. Dunning, Jr., R. J. Harrison, J. Chem. Phys. 1992, 96, 6796-6806.
45. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision A.1, Gaussian, Inc., Pittsburgh PA, 2003.
46. a) C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154-2161;
47. b) C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.