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Volumn 113, Issue 23, 2009, Pages 6524-6530

Energetics of terf-butoxyl addition reaction to norbornadiene: A method for estimating the π-bond strength of a carbon-carbon double bond

Author keywords

[No Author keywords available]

Indexed keywords

A-CARBON; ABSTRACTION REACTIONS; ADDITION METHOD; ADDITION PRODUCTS; BOND DISSOCIATION ENTHALPIES; BOND STRENGTH; CYCLIC ALKENES; NORBORNADIENE; NORBORNENE; RADICAL ADDITION REACTIONS; TIME-RESOLVED PHOTOACOUSTIC CALORIMETRY;

EID: 66649100489     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp900089t     Document Type: Article
Times cited : (6)

References (47)
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    • Sound Analysis, version 1.50D; Quantum Northwest: Spokane, WA, 1999.
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    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, L, Martin, R. L, Fox, D. J, Keit
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
  • 27
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    • It should be noted that even, if this estimate is wrong by 50, the variation in the final value of DHπ, calculated through eq 8 is only ca. 3 kJ mol-1
    • -1.
  • 34
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    • 5,g).
    • 5,g).
  • 36
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    • △1H2° (gas)/2, △rH2°(sln)/2, △ slnH°(C7H9, △ slnH°(t-BuO•)△slnH°(C7H 9-O-t-Bu) but the solvation terms in benzene should cancel out. As shown below, the DHπ value for norbornadiene obtained in the gas phase using the addition reaction, of methoxyl radical (Table 1) and the DHπ derived using eq 8 are identical, suggesting that this assumption is correct
    • π derived using eq 8 are identical, suggesting that this assumption is correct.
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    • NIST Standard Reference Database Number 69; Linstrom, P. J, Mallard, W. G, Eds, Gaithersburg MD
    • Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. In NIST Chemistry WebBook; NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg MD, 2005. http://webbook.nist.gov.
    • (2005) NIST Chemistry WebBook
    • Afeefy, H.Y.1    Liebman, J.F.2    Stein, S.E.3
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.