Photochemical α-cleavage of ketones: Revisiting acetone

Photochemical and Photobiological Sciences

Volumn 3, Issue 1, 2004, Pages 6-16

  Haas, Yehuda ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; ACETONE; FORMALDEHYDE; KETONE DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DISSOCIATION CONSTANT; EXCITATION; FLUORESCENCE ANALYSIS; MOLECULE; PHOTOCHEMICAL QUENCHING; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; QUANTUM YIELD; RADIATION ENERGY; REVIEW; TIME;

EID: 3042688699     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b307997j     Document Type: Article

References (82)

1. J. G. Calvert and J. N. Pitts, Photochemistry, Wiley, New York, 1966, p. 379.
2. J. A. Kerr and M. J. Patronage, Evaluated Kinetic Data on Gas Phase Hydrogen Transfer Reactions of Methyl Radicals, Butterworth, London, 1976, p. 171., cited by:.
3. S. H. Mousavipour P. D. Pacey Initiation and abstraction reactions in the pyrolysis of acetone J. Phys. Chem. 1996 100 3593.
4. R. G. W. Norrish H. G. Crone O. D. Saltmarsh Primary photochemical reactions. Part V. The spectroscopy and photochemical decomposition of acetone J. Chem. Soc. 1934 1456.
5. A. Noyes, Jr. G. B. Porter E. Jolley The primary photochemical process in simple ketones Chem. Rev. 1956 56 49.
6. P. J. Wagner Chemistry of excited triplet organic carbonyl compounds Curr. Top. Chem. 1976 66 1.
7. N. J. Turro, Modern Molecular Photochemistry, Benjamin/Cummings, Menlo Park, CA, 1978.
8. R. G. W. Norrish The primary photochemical production of some free radicals Trans. Faraday Soc. 1934 30 103.
9. R. G. W. Norrish F. W. Kirkbride Primary photochemical reactions. Part I. The decomposition of formaldehyde J. Chem. Soc. 1932 1518.
10. A. Horowitz C. J. Karshner J. G. Calvert Primary processes in the photolysis of acetaldehyde at 3000 Å and 25 °C J. Phys. Chem. 1982 86 3094.
11. P. D. Lightfoot S. P. Kirwan M. J. Pilling Photolysis of acetone at 193.3 nm J. Phys. Chem. 1988 92 4938.
12. S. W. North D. A. Blank J. D. Gezelter C. A. Longfellow Y. T. Lee Evidence for stepwise dissociation dynamics in acetone at 248 and 193 nm J. Chem. Phys. 1995 102 4447.
13. F. O. Rice K. F. Herzfeld The thermal decomposition of organic compounds from the standpoint of free radicals. VI. The mechanism of some chain reactions J. Am. Chem. Soc. 1934 284.
14. E. J. Bowen E. L. A. E. de la Praudiere The photoreactions of liquid and dissolved ketones, part I J. Chem. Soc. 1934 1503.
15. P. E. Frankenberg W. A. Noyes Photochemical studies, XLVII. Liquid acetone-oxygen and liquid acetone-heptane-oxygen J. Am. Chem. Soc. 1953 75 2847.
16. G. S. Hammond N. J. Turro Organic photochemistry Science 1963 142 1541.
17. W. A. Watkins W. M. Word Addition of methyl radicals to carbon monoxide: chemically and thermally activated decomposition of acetyl radical Int. J. Chem. Kinet. 1974 6 855.
18. R. C. Ferris S. Haynes Formation of ketene in the photolysis of acetone J. Am. Chem. Soc. 1950 72 893.
19. C. B. Moore J. C. Weisshaar Radiative, collisional and dissociative processes in triplet acetone Annu. Rev. Phys. Chem. 1983 34 525.
20. C. B. Moore I. W. M. Smith State-resolved studies of reactions in the gas phase, Centennial Issue J. Phys. Chem. 1996 100 12848.
21. CRC Handbook of Chemistry and Physics, CRC Press, Boca Raton, 60th edn., 1980, p. F-232.
22. 1(n, π*) states of acetaldehyde and acetone in supersonic nozzle beam: methyl internal rotation and C═O out-of-plane wagging J. Chem. Phys. 1985 82 3938.
23. 3 photofragments following (n, π*) excitation of acetone Chem. Phys. 1991 155 149.
24. H. Zuckermann B. Schmitz Y. Haas Acetone photophysics in seeded supersonic molecular beams J. Phys. Chem. 1989 93 4083.
25. J. Heicklen W. A. Noyes, Jr. The photolysis and fluorescence of acetone and acetone-biacetyl mixtures J. Am. Chem. Soc. 1959 81 3858.
26. G. H. Damon F. Daniels The photolysis of gaseous acetone and the influence of water J. Am. Chem. Soc. 1933 35 2363.
27. M. E. S. Appleyard R. G. W. Norrish J. Chem. Soc. 1934 1456.
28. S. P. Vaish R. D. McAlpine M. Cocivera Photochemistry of acetone in liquid phase studied by CIDNP [chemically induced dynamic nuclear polarization] J. Am. Chem. Soc. 1974 96 1683.
29. H. Schuh E. J. Hamilton H. Paul H. Fisher Reaction rates of t-butyl and pyvaloyl radicals in solution Helv. Chim. Acta 1974 57 2011.
30. K. Muller G. L. Closs Effect of nuclear spin relaxation on intensity pattern of multiplet spectra in chemically induced dynamic nuclear polarization J. Am. Chem. Soc. 1972 94 1002.
31. G. L. Closs C. E. Doubleday Chemically induced dynamic nuclear spin polarization derived from biradicals generated by photochemical cleavage of cyclic ketones, and the observation of a solvent effect on signal intensities J. Am. Chem. Soc. 1972 94 9248.
32. M. Tomkiewicz A. Goren M. Cocivera Nuclear spin polarization during the photolysis of di-t-butyl ketone J. Chem. Phys. 1972 56 5850.
33. A. Gilbert and J. Baggot, Essentials of Molecular Photochemistry, CRC Press, Boca Raton, 1991.
34. M. Klessinger and J. Michl, Excited States and Photochemistry of Organic Molecules, VCH, New York, 1995.
35. F. Bernardi M. Olivucci M. A. Robb Predicting forbidden and allowed cycloaddition reactions: potential surface topology and its rationalization Acc. Chem. Res. 1990 23 405.
36. S. Zilberg Y. Haas Conical intersections in molecular photochemistry – the role of phase change Chem. Phys. 2000 259 249.
37. G. N. Lewis M. Kasha Phosphorescence and the triplet state J. Am. Chem. Soc. 1944 66 2100.
38. G. Porter M. Windsor The triplet state in fluid media Proc. R. Soc. London, Ser. A 1958 245 238.
39. G. S. Hammond N. J. Turro P. A. Leermakers The mechanisms of photoreactions in solution. IX. Energy transfer from the triplet states of aldehydes and ketones to unsaturated compounds J. Phys. Chem. 1962 66 1144.
40. 2 and hd J. Mol. Spectrosc. 1969 30 365.
41. D. J. Clouthier D. A. Ramsay The spectroscopy of formaldehyde and thioformaldehyde Annu. Rev. Phys. Chem. 1983 34 31.
42. R. E. Rebbert P. Ausloos Triplet-state energy transfer from acetone to aliphatic aldehydes in the gas phase J. Am. Chem. Soc. 1964 86 4803.
43. R. F. Borkman D. R. Kearns Electronic relaxation processes in acetone J. Chem. Phys. 1966 44 945.
44. M. A. El-Sayed Spin–orbit coupling and the radiationless processes in nitrogen heterocyclics J. Chem. Phys. 1963 38 2834.
45. C. W. Larson H. E. O’Neal The gas phase photolysis of acetone at 3130 Å in the presence of hydrogen bromide. A study of the primary photochemical decomposition processes of acetone J. Phys. Chem. 1966 70 2475.
46. R. B. Cundall A. S. Davis The mechanism of the gas phase photolysis of acetone Proc. R. Soc. London, Ser. A 1966 290 563.
47. L. Salem Surface crossings, and surface touchings in photochemistry J. Am. Chem. Soc. 1974 96 3486.
48. W. G. Dauben L. Salem N. J. Turro Classification of photochemical reactions Acc. Chem. Res. 1975 8 41.
49. N. J. Turro W. E. Farneth A. Devaquet Salem diagrams as a device for the elucidation of photochemical reaction mechanisms. Applications to the cleavage of cyclic alkanones J. Am. Chem. Soc. 1976 98 7425.
50. H. E. O’Neal C. W. Larson Primary processes in the acetone photochemical system J. Phys. Chem. 1969 73 1011.
51. A. M. Halpern W. R. Ware Excited singlet radiative and nonradiative transition probabilities for acetone, acetone-d6, and hexafluoroacetone in the gas phase, in solution and in the neat liquid J. Chem. Phys. 1971 54 1271.
52. G. M. Breuer E. K. C. Lee Fluorescence decay times of cyclic ketones, acetone, and butanal in the gas phase J. Phys. Chem. 1971 75 989.
53. D. A. Hansen E. K. C. Lee Radiative and nonradiative transitions in the first excited singlet state of symmetrical methyl-substituted acetones J. Chem. Phys. 1975 62 183.
54. F. S. Wettack G. D. Renkes M. G. Rockley N. J. Turro J. C. Dalton Quenching of alkyl ketone fluorescence by 1,3-dienes J. Am. Chem. Soc. 1970 92 1793.
55. N. C. Yang E. D. Feit M. H. Hui N. J. Turro, J. C. Dalton Photochemistry of di-tert-butyl ketone and structural effects on the rate and efficiency of intersystem crossing of aliphatic ketones J. Am. Chem. Soc. 1970 92 6974.
56. J. C. Dalton K. Dawes N. J. Turro D. S. Weiss J. A. Barltrop J. D. Coyle J. Molecular Photochemistry. XLVIII. Type I and type II photochemical reactions of some five- and six-membered cycloalkanones J. Am. Chem. Soc. 1971 93 7213.
57. S. J. Strickler R. A. Berg Relationship between absorption intensity and fluorescence lifetime of molecules J. Chem. Phys. 1962 37 814.
58. E. K. C. Lee R. S. Lewis Photochemistry of simple aldehydes and ketones in the gas phase Adv. Photochem. 1980 12 1.
59. G. D. Greenblat S. Ruhman Y. Haas Fluorescence decay kinetics of acetone vapor at low pressures Chem. Phys. Lett. 1984 112 200.
60. H. Zuckermann Y. Haas M. Drabbels J. Heinze W. L. Meerts J. Reuss J. van Bladel Acetone, a laser-induced fluorescence study with rotational resolution at 320 nm Chem. Phys. 1992 163 193.
61. O. Anner H. Zuckermann Y. Haas Fluorescence decay of jet-cooled acetone J. Phys. Chem. 1985 89 1336.
62. Y. Haas H. Zuckermann Photodynamics of small aliphatic ketones in a supersonic jet expansion Isr. J. Chem. 1989 29 405.
63. R. D. Levine and R. B. Bernstein, Molecular Reaction Dynamics, Oxford University Press, Oxford, 1974, ch. 5.
64. G. W. Robinson R. P. Frosch Electronic excitation transfer and relaxation J. Chem. Phys. 1962 38 1187.
65. W. Siebrand Radiationless transitions in polyatomic molecules. I. Calculation of Franck–Condon factors J. Chem. Phys. 1967 46 440.
66. Y. Haas G. Stein Pathways of radiative and radiationless transitions in europium(III) solutions. The role of high energy vibrations J. Phys. Chem. 1971 75 3677.
67. R. A. Copeland D. R. Crossley Radiative, collisional and dissociative processes in triplet acetone Chem. Phys. Lett. 1985 115 362.
68. J. Solomon C. Jonah P. Chandra R. Bersohn Photolysis mapping studies of aliphatic carbonyl compounds J. Chem. Phys. 1971 55 362.
69. 3+ CO: resolving the issue of concertedness J. Chem. Phys. 1995 103 477.
70. 1 state and 3s Rydberg state J. Chem. Phys. 1999 110 192.
71. 2 states of acetone J. Chem. Phys. 1999 110 11206.
72. 2CO, and HDCO J. Chem. Phys. 1987 87 3855.
73. 0 formaldehyde eigenstates at the dissociation threshold J. Chem. Phys. 1990 92 3453.
74. R. Walsh S. W. Benson Kinetics and mechanism of the gas phase reaction between iodine and formaldehyde and the carbon-hydrogen bond strength in formaldehyde J. Am. Chem. Soc. 1966 88 4570.
75. F. Polik C. B. Moore A transition state theory-based statistical distribution of unimolecular decay rates with application to unimolecular decomposition of formaldehyde J. Chem. Phys. 1990 93 5657.
76. R. J. Gill G. H. Atkinson Wavelength dependence of HCO formation in the photolysis of acetaldehyde Chem. Phys. Lett. 1979 64 426.
77. M. Noble E. K. C. Lee The singlet π*←n spectrum of jet-cooled acetaldehyde J. Chem. Phys. 1982 78 2219.
78. T. Kono M. Takayanagi T. Nishiya I. Hanazaki Photodissociation of acetaldehyde studied by photofragment excitation spectroscopy in a supersonic free jet Chem. Phys. Lett. 1993 201 166.
79. 1 dynamics of acetaldehyde Chem. Phys. Lett. 1996 261 443.
80. C.-H. Huang V. Chien C.-K. Ni A. H. Kung I-C. Chen State-resolved dynamics of dissociation of triplet acetaldehyde: rate of appearance of fragment HCO and decay of excited states of parent molecule J. Phys. Chem. 2000 104 10362.
81. 2CO J. Chem. Phys. 1998 109 1293.
82. J. S. Yadav J. D. Goddard Acetaldehyde photochemistry: the radical and molecular dissociations J. Chem. Phys. 1986 84 2682.