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Volumn 75, Issue 11, 2010, Pages 3678-3684

Thermodynamic aspects of thermal decomposition and charge-transfer-induced chemiluminescent decomposition for bicyclic dioxetanes bearing a 4-(Benzothiazol-2-yl)-3-hydroxyphenyl moiety

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SUBSTITUENT; CRYSTALLOGRAPHIC ANALYSIS; DIOXETANES; FREE-ENERGY DIFFERENCE; NEGATIVE VALUES; THERMAL DECOMPOSITIONS; THERMODYNAMIC ASPECTS; THERMODYNAMIC CHARACTERISTICS;

EID: 77952989298     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100449m     Document Type: Article
Times cited : (28)

References (66)
  • 1
    • 0041748306 scopus 로고
    • For reviews of 1,2-dioxetane, see: Wasserman, H. H., Murray, R. W., Eds.,Academic Press: New York
    • For reviews of 1,2-dioxetane, see: Bartlett, P. D.; Landis, M. E. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; pp 243 - 286.
    • (1979) Singlet Oxygen , pp. 243-286
    • Bartlett, P.D.1    Landis, M.E.2
  • 2
    • 0002495423 scopus 로고
    • Patai S., Ed.; Wiley: New York
    • Adam, W. In The Chemistry of Peroxide; Patai, S., Ed.; Wiley: New York, 1983; pp 829 - 920.
    • (1983) The Chemistry of Peroxide , pp. 829-920
    • Adam, W.1
  • 3
    • 0001839208 scopus 로고
    • Hassner A., Ed.; Wiley: New York
    • Adam, W. In Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1986; pp 351 - 429.
    • (1986) Small Ring Heterocycles , pp. 351-429
    • Adam, W.1
  • 6
    • 33846213502 scopus 로고    scopus 로고
    • Rappoport Z., Ed.; Wiley: New York
    • Adam, W.; Trofimov, A. V. In The Chemistry of Peroxides; Rappoport, Z., Ed.; Wiley: New York, 2006; Vol. 2, pp 1171 - 1209.
    • (2006) The Chemistry of Peroxides , vol.2 , pp. 1171-1209
    • Adam, W.1    Trofimov, A.V.2
  • 11
    • 0025081418 scopus 로고
    • For reviews of dioxetane-based chemiluminescence, see
    • For reviews of dioxetane-based chemiluminescence, see: Beck, S.; Köster, H. Anal. Chem. 1990, 62, 2258-2270
    • (1990) Anal. Chem. , vol.62 , pp. 2258-2270
    • Beck, S.1    Köster, H.2
  • 32
    • 77952962485 scopus 로고    scopus 로고
    • note
    • A diradical mechanism described here includes an extremely short-lived diradical or diradicaloid for which O-O and C-C bonds cleave in a concerted, but not simultaneous, manner. (1b, 1g)
  • 33
    • 77952972661 scopus 로고    scopus 로고
    • note
    • The chemiluminescent (CL) decomposition of hydroxyphenyl-substituted dioxetanes has been proposed to proceed by the CIEEL (10) (chemically initiated electron exchange luminescence) mechanism, where an initially formed radical ion pair annihilates by back-electron transfer (BET) to give an excited aromatic carbonyl compound. However, the question of whether such a CL reaction includes BET as a fundamental process is still being argued and remains unclear. Therefore, we have recently been using the term CTID, which includes CIEEL and other CT-induced mechanisms.
  • 39
    • 0013270761 scopus 로고    scopus 로고
    • Hastings, J. W.; Kricka, L. J.; Stanley, P. E., Eds.; Wiley: New York
    • McCapra, F. In Chemiluminescence and Bioluminescence; Hastings, J. W.; Kricka, L. J.; Stanley, P. E., Eds.; Wiley: New York, 1996; pp 7 - 15.
    • (1996) Chemiluminescence and Bioluminescence , pp. 7-15
    • McCapra, F.1
  • 44
    • 80052101777 scopus 로고    scopus 로고
    • Tsuji, A.; Matsumoto, M.; Maeda, M.; Kricka, L. J.; Stanley, P. E., Eds.; World Scientific: Singapore
    • Tanaka, J.; Tanaka, C.; Matsumoto, M. In Bioluminescence and Chemiluminescence; Tsuji, A.; Matsumoto, M.; Maeda, M.; Kricka, L. J.; Stanley, P. E., Eds.; World Scientific: Singapore, 2004; pp 205 - 208.
    • (2004) Bioluminescence and Chemiluminescence , pp. 205-208
    • Tanaka, J.1    Tanaka, C.2    Matsumoto, M.3
  • 45
    • 80052101777 scopus 로고    scopus 로고
    • Tsuji, A.; Matsumoto, M.; Maeda, M.; Kricka, L. J.; Stanley, P. E., Eds.; World Scientific: Singapore
    • Tanaka, C.; Tanaka, J.; Matsumoto, M. In Bioluminescence and Chemiluminescence; Tsuji, A.; Matsumoto, M.; Maeda, M.; Kricka, L. J.; Stanley, P. E., Eds.; World Scientific: Singapore, 2004; pp 209 - 212.
    • (2004) Bioluminescence and Chemiluminescence , pp. 209-212
    • Tanaka, C.1    Tanaka, J.2    Matsumoto, M.3
  • 50
    • 77953009145 scopus 로고    scopus 로고
    • note
    • Although dihydrofurans 2a - c with allylic hydrogen(s) could undergo "ene" reaction as well as 1,2-addition of singlet oxygen, the formation of allylic hydroperoxides was not observed. (15) Dihydrofuran 2e underwent selectively 1,2-addition, though dioxetane 1e was obtained as a mixture including 20-40% of decomposition product 9e.
  • 51
    • 0001347157 scopus 로고
    • Sensitized photooxygenation of olefins
    • For reviews of singlet oxygen, see:;. In; Wiley: New York
    • For reviews of singlet oxygen, see: Denny, R. W.; Nickon, A. Sensitized Photooxygenation of Olefins. In Organic Reactions; Wiley: New York, 1973; Vol. 20, pp 133 - 336.
    • (1973) Organic Reactions , vol.20 , pp. 133-336
    • Denny, R.W.1    Nickon, A.2
  • 52
    • 0000992276 scopus 로고
    • Wasserman, H. H.; Murray, R. W., Eds.; Academic Press: New York
    • Schaap, A. P.; Zaklica, K. A. In Singlet Oxygen; Wasserman, H. H.; Murray, R. W., Eds.; Academic Press: New York, 1979; pp 173 - 242.
    • (1979) Singlet Oxygen , pp. 173-242
    • Schaap, A.P.1    Zaklica, K.A.2
  • 53
    • 0013504090 scopus 로고
    • Frimer A.A., Ed.; CRC Press: Boca Raton
    • Baumstark, A. L. In Singlet O2; Frimer, A. A., Ed.; CRC Press: Boca Raton, 1985; Vol. 2, pp 1 - 35.
    • (1985) Singlet O2 , vol.2 , pp. 1-35
    • Baumstark, A.L.1
  • 58
    • 77953015070 scopus 로고    scopus 로고
    • note
    • TBAF-triggered decomposition of a hydroxyphenyl-substituted dioxetane is consecutive, comprising initial deprotonation giving an oxidophenyl-substituted dioxetane and its subsequent CTID so that the rate of the decomposition of dioxetane depends on both TBAF concentration and the substrate. However, the rate of decomposition followed pseudo-first-order kinetics independent of the TBAF concentration when an excess of fluoride concentration (TBAF/dioxetane > ca. 200) was used. Such a kinetic analysis has been well documented for siloxyphenyl-subsituted dioxetane by Adam et.al. (19)
  • 60
    • 77953015744 scopus 로고    scopus 로고
    • note
    • CL was estimated based on the value 0.29 for the chemiluminescent decomposition of 3-adamantylidene-4-methoxy-4-(3-oxidophenyl)- 1,2-dioxetane in a TBAF/DMSO system. (19)
  • 63
    • 77953009472 scopus 로고    scopus 로고
    • note
    • a = 2.1 for 2-(benzoxazol-2-yl)phenol and 4.3 for 2-(benzimidazol-2-yl)phenol.
  • 66
    • 77952990577 scopus 로고    scopus 로고
    • note
    • Solvation with acetonitrile molecules clustered around the oxido group of 1 should also participate in the change of entropy term for the CTID: solvation of the oxido group would be weaker as the size of R increases and the increase in mobility of solvent molecules would not be as large in going from 1a to 1d.


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