Contrasting pKa Shifts in Cucurbit[7]uril Host-Guest Complexes Governed by an Interplay of Hydrophobic Effects and Electrostatic Interactions

被引：40
|
作者：
Basilio, Nuno [1 ]
Gago, Sandra [1 ]
Jorge Parola, A. [1 ]
Pina, Fernando [1 ]
机构：
[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, LAQV,REQUIMTE, P-2829516 Caparica, Portugal
来源：
ACS OMEGA | 2017年 / 2卷 / 01期
关键词：
HIGH-ENERGY WATER; SUPRAMOLECULAR CATALYSIS; STABILIZATION; CONTAINERS; RELEASE; ENHANCE; ANALOGS; DYE;
D O I：
10.1021/acsomega.6b00427
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cucurbit[7]uril inclusion complexes with guests bearing dimethylamino groups show the expected upward pK(a) shifts, whereas their diethylamino counterparts display a decrease in pK(a) due to the preferential stabilization of the unprotonated form. These results identify the diethylamino group as the substituent of choice to avoid receptor-assisted protonation of guest molecules and present new evidence for the role of the hydrophobic effect as a driving force in cucurbituril complexation.
引用
收藏
页码：70 / 75
页数：6
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