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Volumn 115, Issue 5, 2011, Pages 2187-2195

Why does gold(III) porphyrin act as a selective catalyst in the cycloisomerization of allenones?

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC STRUCTURES; C-C BOND FORMATION; CATALYZED REACTIONS; CHEMOSELECTIVE CATALYST; CYCLIZATION PATHWAYS; CYCLOISOMERIZATIONS; GOLD PORPHYRINS; ITS EFFICIENCIES; LOWER ENERGIES; ORBITAL INTERACTION; RING CLOSURES; SELECTIVE CATALYSTS; STERIC FACTOR; SYNTHETIC UTILITY; TRANSITION STATE;

EID: 79952638288     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp1101384     Document Type: Article
Times cited : (32)

References (63)
  • 40
    • 0038626673 scopus 로고    scopus 로고
    • Gaussian, Inc.: Wallingford, CT.
    • Frisch, M. J.; Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2003.
    • (2003) Gaussian 03
    • Frisch, M.J.1
  • 49
    • 79952685143 scopus 로고    scopus 로고
    • note
    • The allenone can, in principle, undergo a keto-enol tautomerism to form a cis -3-butyn-enol or cis -3-bytyn-1-one, which can interact with the Au(III) center through the C - C triple bond. However, B3LYP/6-31+G(d) calculations predict that both cis -3-butyn-enol and cis -3-bytyn-1-one are higher in energy (by 18.1 kcal/mol (16.2 kcal/mol in acetone) and 9.8 kcal/mol (9.0 kcal/mol), respectively) than allenone, suggesting that such a mechanism will be unlikely.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.