메뉴 건너뛰기




Volumn 112, Issue 38, 2008, Pages 8999-9004

Reaction of iminopropadienones with amines: Mechanistic explanations of zwitterionic intermediate, ketene and ketenimine formation

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; AMINATION; AMINES; DENSITY FUNCTIONAL THEORY; GAS DYNAMICS; GASES; HYDROGEN; MATRIX ALGEBRA; OLIGOMERS; PROBABILITY DENSITY FUNCTION;

EID: 84962446726     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp803352m     Document Type: Article
Times cited : (7)

References (41)
  • 10
    • 84962375702 scopus 로고    scopus 로고
    • 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, I, 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, I.; 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 C2; Gaussian, Inc.: Pittsburgh, PA, 2004.
  • 24
    • 0034500213 scopus 로고    scopus 로고
    • Our results confirm an earlier study on dimethylamine di- and trimers
    • Cabaleiro-Lago, E. M.; Rios, M. A. Our results confirm an earlier study on dimethylamine di- and trimers. J. Chem. Phys. 2000, 113, 9523.
    • (2000) J. Chem. Phys , vol.113 , pp. 9523
    • Cabaleiro-Lago, E.M.1    Rios, M.A.2
  • 28
    • 84962409272 scopus 로고    scopus 로고
    • These findings are confirmed by calculations at several additional levels of theory: neither the improvement of electron correlation nor the combination with larger (or smaller) basis sets led to the localization of the missing transition state and zwitterion. However, gas phase calculations at the HF/6-31G(d) level yield these structures, which are also found when including a simulated solvent field in DFT optimizations.
    • These findings are confirmed by calculations at several additional levels of theory: neither the improvement of electron correlation nor the combination with larger (or smaller) basis sets led to the localization of the missing transition state and zwitterion. However, gas phase calculations at the HF/6-31G(d) level yield these structures, which are also found when including a simulated solvent field in DFT optimizations.
  • 31
    • 84962337438 scopus 로고    scopus 로고
    • 21 could not be located at various levels of theory.
    • 21 could not be located at various levels of theory.
  • 37
    • 0000561658 scopus 로고    scopus 로고
    • n,-ArN=C(OMe)CH=C=O), most dramatically with pentafluorophenyl
    • n,-ArN=C(OMe)CH=C=O), most dramatically with pentafluorophenyl
  • 38
    • 84962413881 scopus 로고    scopus 로고
    • (Fulloon, B. E PhD. Thesis, The University of Queensland, Brisbane, 1997,).
    • (Fulloon, B. E PhD. Thesis, The University of Queensland, Brisbane, 1997,).
  • 40
    • 84962446241 scopus 로고    scopus 로고
    • Only the most consistent data, i.e, similar geometrical arrangement, number of coordinations and a complete (reactant to product) sequence, is presented herein. They represent also the pathways that possess the lowest overall energy. There are individual structures that lie lower in energy than the respective ones presented but no connection to the overall process could be found
    • Only the most consistent data, i.e., similar geometrical arrangement, number of coordinations and a complete (reactant to product) sequence, is presented herein. They represent also the pathways that possess the lowest overall energy. There are individual structures that lie lower in energy than the respective ones presented but no connection to the overall process could be found.
  • 41
    • 84962391691 scopus 로고    scopus 로고
    • For the complete mechanism, only the initial addition to a double bond is important and subsequent hydrogen relay is not For each of these first transition states, only two different structures could be located and the one presented is significantly lower in energy
    • For the complete mechanism, only the initial addition to a double bond is important and subsequent hydrogen relay is not For each of these first transition states, only two different structures could be located and the one presented is significantly lower in energy.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.