caa a22 4500 605513104 CHVBK 20210128100658.0 cr unu---uuuuu 210128e20150501xx s 000 0 eng 10.1007/s00894-015-2680-7 doi (NATIONALLICENCE)springer-10.1007/s00894-015-2680-7 The reactivity of phenancyl bromide under β-cyclodextrin as supramolecular catalyst: a computational survey [Elektronische Daten] [Yali Wan, Xueye Wang, Na Liu] 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 Springer-Verlag Berlin Heidelberg, 2015 β-Cyclodextrin (β-CD) nationallicence Density functional theory (DFT) nationallicence Inclusion complex nationallicence Phenacyl bromide nationallicence Supramolecular catalyst nationallicence Wan Yali 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 aut Wang Xueye 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 aut Liu Na 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 aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-7 1610-2940 21:5<1 2015 21 894 https://doi.org/10.1007/s00894-015-2680-7 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2680-7 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Wan Yali 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 aut NATIONALLICENCE 700 1- Wang Xueye 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 aut NATIONALLICENCE 700 1- Liu Na 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 aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-7 1610-2940 21:5<1 2015 21 894