| Item type |
デフォルトアイテムタイプ_（フル）(1) |
| 公開日 |
2023-03-18 |
| タイトル |
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|
タイトル |
Origin of the axial-alkyl preference of (R)-alpha-phellandrene and related compounds investigated by high-level ab initio MO calculations. Importance of the CH/pi hydrogen bond |
|
言語 |
en |
| 作成者 |
Takahashi, Osamu
Yamasaki, Katsuyoshi
Kohno, Yuji
Ueda, Kazuyoshi
Suezawa, Hiroko
Nishio, Motohiro
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| アクセス権 |
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アクセス権 |
open access |
|
アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 権利情報 |
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|
権利情報 |
Copyright (c) 2008 Elsevier Ltd |
| 主題 |
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|
主題Scheme |
NDC |
|
主題 |
430 |
| 内容記述 |
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内容記述 |
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. |
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言語 |
en |
| 出版者 |
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出版者 |
Elsevier Ltd |
| 言語 |
|
|
言語 |
eng |
| 資源タイプ |
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|
資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 出版タイプ |
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|
出版タイプ |
AO |
|
出版タイプResource |
http://purl.org/coar/version/c_b1a7d7d4d402bcce |
| 関連情報 |
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|
識別子タイプ |
DOI |
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|
関連識別子 |
10.1016/j.tet.2008.04.007 |
| 関連情報 |
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関連タイプ |
isVersionOf |
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|
識別子タイプ |
DOI |
|
|
関連識別子 |
http://dx.doi.org/10.1016/j.tet.2008.04.007 |
| 収録物識別子 |
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収録物識別子タイプ |
ISSN |
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収録物識別子 |
0040-4020 |
| 収録物識別子 |
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収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA00861787 |
| 開始ページ |
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|
開始ページ |
5773 |
| 書誌情報 |
Tetrahedron
Tetrahedron
巻 64,
号 24,
p. 5773-5778,
発行日 2008-06
|
| 旧ID |
25572 |
Tetrahedron_64_5773.pdf (199.4 KB)
