The Journal of Organic Chemistry
Article
temperatures and fitting the data in the Arrhenius and Eyring
equations as follows:
(20) Kaanumalle, L. S.; Nithyanandhan, J.; Pattabiraman, M.;
Jayaraman, N.; Ramamurthy, V. J. Am. Chem. Soc. 2004, 126, 8999−
9006.
ln k = ln A − E /RT
a
(21) Natarajan, B.; Gupta, S.; Ramamurthy, V.; Jayaraman, N. J. Org.
Chem. 2011, 76, 4018−4026.
⧧
⧧
(22) Whitten, D. G.; Wildes, P. D.; Pacifici, J. G.; Irick, G. Jr. J. Am.
Chem. Soc. 1971, 93, 2004−2008.
ln(k/T) = −ΔH /RT + ln(k′/h) + ΔS /R
where k is the rate constant; T, temperature; ΔH⧧, enthalpy of activation;
ΔS⧧, entropy of activation; R, molar gas constant; k′, Boltzmann constant;
h, Planck constant.
(23) Song, X.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1997,
119, 9144−9159.
(24) Ueno, A.; Yoshimura, H.; Saka, R.; Osa, T. J. Am. Chem. Soc.
1979, 101, 2779−2780.
The activation free energy (ΔG⧧ was obtained by following
equation
(25) Rau, H. In Photochromism: Molecular and Systems; Durr, H.,
̈
Bouas-Lauran, H., Eds.; Elsevier: Amsterdam, 1990; p 165.
(26) Bortollus, P.; Monti, S. J. Phys. Chem. 1987, 91, 5046−5050.
(27) Zacharias, P. S.; Ameerunisha, S.; Korupoju, S. R. J. Chem. Soc.,
Perkin Trans. 2 1998, 2055−2059.
⧧
⧧
⧧
ΔG = ΔH − TΔS
AUTHOR INFORMATION
■
(28) Otruba, J. P. III; Weiss, R. G. J. Org. Chem. 1983, 48, 3448−
Corresponding Author
3453.
(29) Schanze, K.; Mattox, T. F.; Whitten, D. G. J. Am. Chem. Soc.
1982, 104, 1733−1735.
(30) Bortolus, P.; Monti, S. J. Phys. Chem. 1987, 91, 5046−5050.
(31) Syamala, M. S.; Devanathan, S.; Ramamurthy, V. J. Photochem.
1986, 34, 219−229.
Notes
The authors declare no competing financial interest.
(32) Syamala, M. S.; Ramamurthy, V. J. Org. Chem. 1986, 51, 3712−
3715.
ACKNOWLEDGMENTS
■
(33) Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.;
Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Christopher,
D. J. Am. Chem. Soc. 1964, 86, 3197−3217.
(34) Lewis, F. D.; Bedell, A. M.; Dykstra, R. E.; Elbert, J. E.; Gould,
I. R.; Farid, S. J. Am. Chem. Soc. 1990, 112, 8055−8064.
(35) Lakshminarasimhan, P. H.; Sunoj, R. B.; Karthikeyan, S.;
Chandrashekar, J.; Johnston, L. J.; Ramamurthy, V. J. J. Photochem.
Photobiol. A 2002, 153, 41−53.
N.J. thanks the Department of Science and Technology,
New Delhi, for financial support of the work. V.R. is grateful to
the National Science Foundation for generous financial support
for the project (CHE-0848017). B.N. thanks the Council of
Scientific and Industrial Research, New Delhi, for a research
fellowship.
(36) Isak, S. J.; Eyring, E. M. J. Phys. Chem. 1992, 96, 1738−1742.
(37) Kreller, D. I.; Kamat, P. V. J. Phys. Chem. 1991, 95, 4406−4410.
(38) Monti, S.; Orlandi, G.; Palmieri, P. Chem. Phys. 1982, 71, 87−
99.
(39) Cembran, A.; Bernardi, F.; Garavelli, M.; Gagliardi, L.; Orlandi,
G. J. Am. Chem. Soc. 2004, 126, 3234−3243.
(40) Conti, I.; Marchioni, F.; Credi, A.; Orlandi, G.; Rosini, G.;
Garavelli, M. J. Am. Chem. Soc. 2007, 129, 3198−3210.
(41) Shinkai, S.; Nakaji, T.; Nishida, Y.; Ogawa, T.; Manabe, O.
J. Am. Chem. Soc. 1980, 102, 5860−5865.
(42) Beale, R. N.; Roe, E. M. F. J. Chem. Soc. 1953, 2755−2763.
(43) Cook, A. H.; Jones, D. G.; Polya, J. B. J. Chem. Soc. 1939, 1315−
1320.
REFERENCES
■
(1) Newkome, G. R.; Shreiner, C. Chem. Rev. 2010, 110, 6338−6442.
(2) Astruc, D.; Boisselier, E.; Ornelas, C. Chem. Rev. 2010, 110,
1857−1959.
(3) Rosen, B. M.; Wilson, C. J.; Wilson, D. A.; Peterca, M.; Imam,
M. R.; Percec, V. Chem. Rev. 2009, 109, 6275−6540.
(4) Smith, D. K.; Diederich, F. Chem.Eur. J. 1998, 4, 1353−1361.
́
(5) Tomalia, D. A.; Frechet, J. M. J. J. Polym. Sci., Part A: Polym.
Chem. 2002, 40, 2719−2728.
́
(6) Hawker, C. J.; Wooley, K. L.; Frechet, J. M. J. J. Am. Chem. Soc.
1993, 115, 4375−4376.
(7) Jansen, J. F. G. A.; de Brabander-van den Berg, E. M. M.; Meijer,
E. W. Science 1994, 266, 1226−1229.
(8) Chasse, T. L.; Sachdeva, R.; Li, Q.; Li, Z.; Petrie, R. J.; Gorman,
C. B. J. Am. Chem. Soc. 2003, 125, 8250−8254.
(9) Ong, W.; Grindstaff, J.; Sobransingh, D.; Toba, R.; Quintela,
J. M.; Peinador, C.; Kaifer, A. E. J. Am. Chem. Soc. 2005, 127, 3353−
3361.
(10) Mchedlov-Petrossyan, N. O.; Bryleva, E. Y.; Vodolazkaya, N. A.;
Dissanayake, A. A.; Ford, W. T. Langmuir 2008, 24, 5689−5699.
(11) Burakowska, E.; Quinn, J. R.; Zimmerman, S. C.; Haag, R. J. Am.
Chem. Soc. 2009, 131, 10574−10580.
(12) Kannaiyan, D.; Imae, T. Langmuir 2009, 25, 5282−5285.
(13) Luty, T.; Eckhardt, C. J. J. Am. Chem. Soc. 1995, 117, 2441−52.
(14) Ito, Y.; Yasui, S.; Yamauchi, J.; Ohba, S.; Kano, G. J. Phys. Chem.
A 1998, 102, 5415−5420.
(15) Zimmerman, H. E.; Alabugin, I. V.; Smolenskaya, V. N.
Tetrahedron 2000, 56, 6821−6831.
(16) Xu, J.; Weiss, R. G. Org. Lett. 2003, 5, 3077−3080.
(17) Kaliappan, R.; Ling, Y.; Kaifer, A. E.; Ramamurthy, V. Langmuir
2009, 25, 8982−8992.
(18) Nithyanandhan, J.; Jayaraman, N. J. Org. Chem. 2002, 67, 6282−
6285.
(19) Kaanumalle, L. S.; Ramesh, R.; Maddipatla, V. S. N. M.;
Nithyanandhan, J.; Jayaraman, N.; Ramamurthy, V. J. Org. Chem. 2005,
70, 5062−5069.
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