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Volumn 125, Issue 5, 2003, Pages 1319-1328

Mechanism of ene reactions of singlet oxygen. A two-step no-intermediate mechanism

Author keywords

[No Author keywords available]

Indexed keywords

COMPOSITION; ISOTOPES; OXYGEN;

EID: 0037419851     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027225p     Document Type: Article
Times cited : (260)

References (92)
  • 2
  • 5
    • 0012987190 scopus 로고
    • Windus, T. L.; Gordon, M. S.; Burggraf, L. W.; Davis, L. P. J. Am. Chem. Soc. 1991, 113, 4356. Windus, T. L.; Gordon, M. S. Theor. Chim. Acta 1992, 83, 21.
    • (1992) Theor. Chim. Acta , vol.83 , pp. 21
    • Windus, T.L.1    Gordon, M.S.2
  • 12
    • 0036572670 scopus 로고    scopus 로고
    • Castaño, O.; Palmeiro, R.; Frutos, L. M.; Luisandrés, J. J. Comput. Chem. 2002, 23, 732. See also Wenthold, P. G.; Hrovat, D. A.; Borden, W. T.; Lineberger, W. C. Science 1996, 272, 1456. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc, 1992, 114, 5879.
    • (2002) J. Comput. Chem. , vol.23 , pp. 732
    • Castaño, O.1    Palmeiro, R.2    Frutos, L.M.3    Luisandrés, J.4
  • 13
    • 0000121785 scopus 로고    scopus 로고
    • Castaño, O.; Palmeiro, R.; Frutos, L. M.; Luisandrés, J. J. Comput. Chem. 2002, 23, 732. See also Wenthold, P. G.; Hrovat, D. A.; Borden, W. T.; Lineberger, W. C. Science 1996, 272, 1456. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc, 1992, 114, 5879.
    • (1996) Science , vol.272 , pp. 1456
    • Wenthold, P.G.1    Hrovat, D.A.2    Borden, W.T.3    Lineberger, W.C.4
  • 14
    • 0001683740 scopus 로고
    • Castaño, O.; Palmeiro, R.; Frutos, L. M.; Luisandrés, J. J. Comput. Chem. 2002, 23, 732. See also Wenthold, P. G.; Hrovat, D. A.; Borden, W. T.; Lineberger, W. C. Science 1996, 272, 1456. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc, 1992, 114, 5879.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5879
    • Hrovat, D.A.1    Borden, W.T.2
  • 16
    • 0001114851 scopus 로고    scopus 로고
    • Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 880. Deng, Q.; Thomas, B. E.; Houk, K. N.; Dowd, P. J. Am. Chem. Soc. 1997, 119, 6902.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 880
    • Li, Y.1    Houk, K.N.2
  • 21
    • 0000316306 scopus 로고
    • Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 295. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437. Manring, L. E.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4710. Wilson, S. L.; Schuster, G. B. J. Org. Chem. 1986, 51, 2056. Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 3396.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 295
    • Jefford, C.W.1    Rimbault, C.G.2
  • 22
    • 0000710141 scopus 로고
    • Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 295. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437. Manring, L. E.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4710. Wilson, S. L.; Schuster, G. B. J. Org. Chem. 1986, 51, 2056. Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 3396.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 6437
    • Jefford, C.W.1    Rimbault, C.G.2
  • 23
    • 0020780781 scopus 로고
    • Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 295. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437. Manring, L. E.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4710. Wilson, S. L.; Schuster, G. B. J. Org. Chem. 1986, 51, 2056. Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 3396.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 4710
    • Manring, L.E.1    Foote, C.S.2
  • 24
    • 0013031798 scopus 로고
    • Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 295. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437. Manring, L. E.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4710. Wilson, S. L.; Schuster, G. B. J. Org. Chem. 1986, 51, 2056. Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 3396.
    • (1986) J. Org. Chem. , vol.51 , pp. 2056
    • Wilson, S.L.1    Schuster, G.B.2
  • 25
    • 0012991668 scopus 로고
    • Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 295. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437. Manring, L. E.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 4710. Wilson, S. L.; Schuster, G. B. J. Org. Chem. 1986, 51, 2056. Fenical, W.; Kearns, D. R.; Radlick, P. J. Am. Chem. Soc. 1969, 91, 3396.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 3396
    • Fenical, W.1    Kearns, D.R.2    Radlick, P.3
  • 47
    • 0345891702 scopus 로고    scopus 로고
    • note
    • The RHF calculations predict that a very loose π-complex is formed without a barrier on the approach of singlet oxygen to the pi bond of tetramethylethylene. The energy of the π-complex was -1.1 kcal/mol relative to those of the separate alkene and singlet oxygen. After allowance for basis set superposition error and entropy, this "complex" is unlikely to correspond to a free-energy minimum at 25 °C.v
  • 48
    • 0346522498 scopus 로고    scopus 로고
    • note
    • Spin-projected UB3LYP/6-311++G** puts 18 1.2 kcal/mol above the energy of 17 and 19 5.2 kcal/mol above the energy of 17, virtually identical to the spin-projected UB3LYP/6-31G* energetics.
  • 49
    • 0024841752 scopus 로고
    • For the calculations, the program QUIVER was used (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989) with Becke3LYP and RHF frequencies scaled by 0.9614 and 0.91, respectively (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502).
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8989
    • Saunders, M.1    Laidig, K.E.2    Wolfsberg, M.3
  • 50
    • 0011083273 scopus 로고    scopus 로고
    • For the calculations, the program QUIVER was used (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989) with Becke3LYP and RHF frequencies scaled by 0.9614 and 0.91, respectively (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502).
    • (1996) J. Phys. Chem. , vol.100 , pp. 16502
    • Scott, A.P.1    Radom, L.2
  • 57
    • 0347782945 scopus 로고    scopus 로고
    • note
    • s-symmetric structures by successively decreasing X by 0.1 Å, leaving Y constant, and reoptimizing the geometry at each step.
  • 58
    • 0346522497 scopus 로고    scopus 로고
    • note
    • As the structure departs from the saddle point along the MEP, a low-energy rotational mode in the nonreacting methyl group is loosened, and overall, the entropy is increasing (on the basis of B3LYP frequencies, 298 K). There is thus no indication of a free-energy barrier to the decomposition of the perepoxide.
  • 79
    • 0012311763 scopus 로고
    • Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. Reyes, M. B.; Carpenter, B. K. J. Am. Chem. Soc. 2000, 122, 10163. Reyes, M. B.; Lobkovsky, E. B.; Carpenter, B. K. J. Am. Chem. Soc. 2002, 124, 641. Carpenter, B. K. J. Am. Chem. Soc. 1996, 118, 10329.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6336
    • Carpenter, B.K.1
  • 80
    • 0034684264 scopus 로고    scopus 로고
    • Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. Reyes, M. B.; Carpenter, B. K. J. Am. Chem. Soc. 2000, 122, 10163. Reyes, M. B.; Lobkovsky, E. B.; Carpenter, B. K. J. Am. Chem. Soc. 2002, 124, 641. Carpenter, B. K. J. Am. Chem. Soc. 1996, 118, 10329.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 10163
    • Reyes, M.B.1    Carpenter, B.K.2
  • 81
    • 0037196290 scopus 로고    scopus 로고
    • Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. Reyes, M. B.; Carpenter, B. K. J. Am. Chem. Soc. 2000, 122, 10163. Reyes, M. B.; Lobkovsky, E. B.; Carpenter, B. K. J. Am. Chem. Soc. 2002, 124, 641. Carpenter, B. K. J. Am. Chem. Soc. 1996, 118, 10329.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 641
    • Reyes, M.B.1    Lobkovsky, E.B.2    Carpenter, B.K.3
  • 82
    • 0029905871 scopus 로고    scopus 로고
    • Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. Reyes, M. B.; Carpenter, B. K. J. Am. Chem. Soc. 2000, 122, 10163. Reyes, M. B.; Lobkovsky, E. B.; Carpenter, B. K. J. Am. Chem. Soc. 2002, 124, 641. Carpenter, B. K. J. Am. Chem. Soc. 1996, 118, 10329.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10329
    • Carpenter, B.K.1
  • 83
    • 0001465311 scopus 로고    scopus 로고
    • Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Am. Chem. Soc. 1997, 119, 5251. Doubleday, C.; Nendel, M.; Houk, K. N.; Thweatt, D,; Page, M. J. Am. Chem. Soc. 1999, 121, 4720. Doubleday, C. J. Phys. Chem. 2001, 105, 6333. Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. Doubleday, C.; Li, G.; Hase, W. L. Phys. Chem. Chem. Phys. 2002, 4, 304.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5251
    • Doubleday C., Jr.1    Bolton, K.2    Hase, W.L.3
  • 84
    • 0033583717 scopus 로고    scopus 로고
    • Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Am. Chem. Soc. 1997, 119, 5251. Doubleday, C.; Nendel, M.; Houk, K. N.; Thweatt, D,; Page, M. J. Am. Chem. Soc. 1999, 121, 4720. Doubleday, C. J. Phys. Chem. 2001, 105, 6333. Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. Doubleday, C.; Li, G.; Hase, W. L. Phys. Chem. Chem. Phys. 2002, 4, 304.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4720
    • Doubleday, C.1    Nendel, M.2    Houk, K.N.3    Thweatt, D.4    Page, M.5
  • 85
    • 0035812115 scopus 로고    scopus 로고
    • Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Am. Chem. Soc. 1997, 119, 5251. Doubleday, C.; Nendel, M.; Houk, K. N.; Thweatt, D,; Page, M. J. Am. Chem. Soc. 1999, 121, 4720. Doubleday, C. J. Phys. Chem. 2001, 105, 6333. Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. Doubleday, C.; Li, G.; Hase, W. L. Phys. Chem. Chem. Phys. 2002, 4, 304.
    • (2001) J. Phys. Chem. , vol.105 , pp. 6333
    • Doubleday, C.1
  • 86
    • 0347482791 scopus 로고    scopus 로고
    • Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Am. Chem. Soc. 1997, 119, 5251. Doubleday, C.; Nendel, M.; Houk, K. N.; Thweatt, D,; Page, M. J. Am. Chem. Soc. 1999, 121, 4720. Doubleday, C. J. Phys. Chem. 2001, 105, 6333. Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. Doubleday, C.; Li, G.; Hase, W. L. Phys. Chem. Chem. Phys. 2002, 4, 304.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3648
    • Doubleday C., Jr.1    Bolton, K.2    Hase, W.L.3
  • 87
    • 0036158047 scopus 로고    scopus 로고
    • Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Am. Chem. Soc. 1997, 119, 5251. Doubleday, C.; Nendel, M.; Houk, K. N.; Thweatt, D,; Page, M. J. Am. Chem. Soc. 1999, 121, 4720. Doubleday, C. J. Phys. Chem. 2001, 105, 6333. Doubleday, C., Jr.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. Doubleday, C.; Li, G.; Hase, W. L. Phys. Chem. Chem. Phys. 2002, 4, 304.
    • (2002) Phys. Chem. Chem. Phys. , vol.4 , pp. 304
    • Doubleday, C.1    Li, G.2    Hase, W.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.