Art

J-GLOBAL ID：200902175473189638   Reference number：02A0667744

The Conformation of 2-Phenylpropionaldehyde and Alkyl 1-Phenylethyl Ketones as Evidenced by Ab Initio Calculations. Relevance of the CH/π and CH/O Interactions in Stereochemistry.

2-フェニルプロピオンアルデヒドおよびアルキル1-フェニルエチルケトンの立体配座のab initio計算による証明 立体化学におけるCH/πおよびCH/O相互作用の関連性

Author (6)： TAKAHASHI O (Hiroshima Univ., Hiroshima) ,  YASUNAGA K (Hiroshima Univ., Hiroshima) ,  GONDOH Y (Hiroshima Univ., Hiroshima) ,  KOHNO Y (Hiroshima Univ., Hiroshima) ,  SAITO K (Hiroshima Univ., Hiroshima) ,  NISHIO M (CHPI Inst., Tokyo)
Material： Bulletin of the Chemical Society of Japan  (Bull Chem Soc Jpn)
Volume： 75  Issue： 8  Page： 1777-1783  Publication year： Aug. 15, 2002 
JST Material Number： G0450A  ISSN： 0009-2673  CODEN： BCSJA8  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *steric conformation ,...

   To see more with JDream III (charged).   {{ this.onShowAbsJLink("http://jdream3.com/lp/jglobal/index.html?docNo=02A0667744&from=J-GLOBAL&jstjournalNo=G0450A") }}

JST classification (2)： Configuration and conformation of molecules  (BH05022J) ,  Aromatic monocyclic aldehydes  (CF05160X)

Substance index (8)： Propionaldehyde ,  (S)-2-Phenylpropanal ,  (S)-3-Phenyl-2-butanone ,  (S)-2-Phenyl-3-pentanone ,  Isopropyl[(S)-α-methylbenzyl] ketone ,  [(S)-α-Methylbenzyl]tert-butyl ketone ,  Formic acid methyl ,  N-Methylformamide

Reference (85)：

• 1) S. Zushi, Y. Kodama, K. Nishihata, K. Umemura, M. Nishio, J. Uzawa, and M. Hirota, Bull. Chem. Soc. Jpn., 53, 3631 (1980).
• 2) The NMR experiments suggested two rotamers with R/Ph synclinal structure (φ ca. 30° and 90°) to preponderate. The reason remains unclear why the minimum corresponding to rotamer a (φ 60°) split into two minima but it may be an artifact brought about by using inappropriate model (e.g., wrong assumption for the LSR···O=C distance) in the simulation procedure.
• 3) M. Hirota, T. Sekiya, K. Abe, H. Tashiro, M. Karatsu, M. Nishio, and E. Osawa, Tetrahedron, 39, 3091 (1983).
• 4) M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, “Gaussian 98, Revision A.4,” Gaussian Inc., Pittsburgh, PA (1998).
• 5) U. C. Singh and P. A. Kollman, J. Comput. Chem., 5, 129 (1984);

Terms in the title (9)： 2-フェニルプロピオンアルデヒド ,  フェニルエチルケトン ,  立体配座 ,  計算 ,  証明 ,  立体化学 ,  CH ,  相互作用 ,  関連性