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ID 25572
本文ファイル
著者
Takahashi, Osamu サステナブル・ディベロップメント実践研究センター 広大研究者総覧
Kohno, Yuji
Ueda, Kazuyoshi
Suezawa, Hiroko
Nishio, Motohiro
NDC
化学
抄録(英)
Ab initio MO calculations were carried out, at the MP2/6-311++G(d,p)//MP2/6-311G(d,p) level, to investigate the Gibbs energy of conformational isomers of (R)-α-phellandrene and related 5-alkyl-1,3-cyclohexadienes. It has been found that the conformer bearing the 5-alkyl group in axial orientation is more stable than the equatorial congener. The result is consistent with experimental evidence that the axial-isopropyl conformer prevails in the conformational equilibrium of α-phellandrene. The reason for the stability of the folded conformer has been sought in the context of the CH/π hydrogen bond. A number of short non-bond distances have been disclosed in the axial conformers, between CHs in the 5-alkyl group and sp2-carbons of the cyclohexadiene ring. We suggest that the stability of the folded conformation often observed in conjugated diene compounds of natural origin, such as α-phellandrene and levopimaric acid, is attributed to an attractive molecular force, the CH/π hydrogen bond.
掲載誌名
Tetrahedron
64巻
24号
開始ページ
5773
終了ページ
5778
出版年月日
2008-06
出版者
Elsevier Ltd
ISSN
0040-4020
NCID
出版者DOI
言語
英語
NII資源タイプ
学術雑誌論文
広大資料タイプ
学術雑誌論文
DCMIタイプ
text
フォーマット
application/pdf
著者版フラグ
author
権利情報
Copyright (c) 2008 Elsevier Ltd
関連情報URL(IsVersionOf)
http://dx.doi.org/10.1016/j.tet.2008.04.007
部局名
理学研究科