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Lactams. XXV. Reassignments of the C=C and C=O Stretching Vibrations in Six-Membered α, β-Unsaturated Lactams
http://hdl.handle.net/2297/7622
http://hdl.handle.net/2297/762296672211-67c5-42da-b440-84f13d2ed5d7
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PH-PR-OHBA-M-2697.pdf (1.1 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2017-10-03 | |||||
| タイトル | ||||||
| タイトル | Lactams. XXV. Reassignments of the C=C and C=O Stretching Vibrations in Six-Membered α, β-Unsaturated Lactams | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
Fujii, Tozo
× Fujii, Tozo× Takai, Yukimi× Ohba, Masashi× Kogen, Hiroshi× Oki, Michinori |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 33, 号 7, p. 2697-2704, 発行日 1985-07-25 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0009-2363 | |||||
| NCID | ||||||
| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA00602100 | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1248/cpb.33.2697 | |||||
| 出版者 | ||||||
| 出版者 | 日本薬学会 | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | A new method for differentiating the lactam CO infrared (IR) absorption from the C=C absorption in the six-membered, α, β-unsaturated lactam system (type 2) has been developed by utilizing association of dichloroacetic acid or a similar carboxylic acid with the lactam CO, which decreases the frequency of the lactam CO absorption by 20-40 cm^<-1>. On the basis of such an association shift as well as the results obtained from solvent shift experiments with the lactams 5,6,15,and 17-19,the lactam CO and the conjugated C=C absorptions observed for each of the α, β-unsaturated lactams 14-19 in the 1590-1670 cm^<-1> region were differentiated from each other. As a result, it has now become clear that in six-membered lactams the carbonyl frequency is slightly (10-20 cm^<-1>) lowered by conjugation with a double bond, in line with the usual lowering. This is the opposite of what has been proposed in the literature. In addition, the deuterated α, β-unsaturated lactam 24 was prepared from the exocyclic methylene lactam 23 by treatment with NaOD in a mixture of D_2O and EtOD. This deuterium labeling was found to decrease the frequency of the 1666 cm^<-1> absorption, assigned to the C=C stretching vibration, by 17 cm^<-1>, supporting the correctness of the above differentiation. | |||||
| 著者版フラグ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
