The reactivity of phenancyl bromide under β-cyclodextrin as supramolecular catalyst: a computational survey
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2680-7 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2680-7 | ||
| 245 | 0 | 4 | |a The reactivity of phenancyl bromide under β-cyclodextrin as supramolecular catalyst: a computational survey |h [Elektronische Daten] |c [Yali Wan, Xueye Wang, Na Liu] |
| 520 | 3 | |a Phenacyl bromide as one starting material in multicomponent reactions (MCRs) with β-cyclodextrin (β-CD) as catalyst can get an excellent yield in short reaction times. The interaction of β-CD with phenacyl bromide plays an important role in this process. This paper studies the complex of β-CD with phenacyl bromide using density functional theory (DFT) method. Energy is investigated to find out the lowest energy of two possible complexation models. Hydrogen bonds are researched on the basis of natural bonding orbital (NBO) analysis. The relative position between phenacyl bromide and β-CD is confirmed by 1H nuclear magnetic resonance (1HNMR). The results of frontier molecular orbitals and charge distribution reveal that β-CD catalyst improves the reactivity and electrophilicity of phenacyl bromide, meanwhile, the carbonyl group of phenacyl bromide more easily gives a carbocationic intermediate in the presence of β-CD as catalyst. The reactivity of phenancyl bromide under β-CD as supramolecular catalysis is improved. Graphical Abstract The reactivity of phenancyl bromide under β-cyclodextrin as supramolecular catalyst | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a β-Cyclodextrin (β-CD) |2 nationallicence | |
| 690 | 7 | |a Density functional theory (DFT) |2 nationallicence | |
| 690 | 7 | |a Inclusion complex |2 nationallicence | |
| 690 | 7 | |a Phenacyl bromide |2 nationallicence | |
| 690 | 7 | |a Supramolecular catalyst |2 nationallicence | |
| 700 | 1 | |a Wan |D Yali |u Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Xiangtan, Hunan, People's Republic of China |4 aut | |
| 700 | 1 | |a Wang |D Xueye |u Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Xiangtan, Hunan, People's Republic of China |4 aut | |
| 700 | 1 | |a Liu |D Na |u Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Xiangtan, Hunan, People's Republic of China |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/5(2015-05-01), 1-7 |x 1610-2940 |q 21:5<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2680-7 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2680-7 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Wan |D Yali |u Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Xiangtan, Hunan, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Wang |D Xueye |u Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Xiangtan, Hunan, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Liu |D Na |u Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, 411105, Xiangtan, Hunan, People's Republic of China |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/5(2015-05-01), 1-7 |x 1610-2940 |q 21:5<1 |1 2015 |2 21 |o 894 | ||