Multiple hydrogen-bonding interactions between macrocyclic triurea and F(-), Cl(-), Br(-), I(-) and NO(3)(-): a theoretical investigation
Chen, YS ; Pan, XL ; Yan, H ; Tan, NH
2011
发表期刊PHYSICAL CHEMISTRY CHEMICAL PHYSICS
ISSN1463-9076
卷号13期号:16页码:7384-7395
摘要The binding behaviors of the 27-membered macrocyclic triurea 1 towards the five anions, F(-), Cl(-), Br(-), I(-) and NO(3)(-), through multiple hydrogen-bonding interactions, were investigated at the B3LYP/6-311++G(d,p)//B3LYP/6-31(1)++GG(d,p) (6-31(1)++GG(d,p) is a hybrid basis set; for more details see computational methods) level. Three binding modes (I, II, and III) were found for all the five anions in the gas phase, and seven structural parameters have been used to describe these binding modes. Binding mode I and II have similar binding geometries and their coordination number of anions is six. Binding mode III exhibits completely different binding characteristics and the coordination number is three except for NO(3)(-). Our calculation revealed that the binding strength of binding modes follows the trend, mode II > I > III, with the exception of F(-) complex. The binding affinity of anions in the gas phase goes in this order: F(-) > Cl(-) > NO(3)(-) > Br(-) > I(-). The changes in the binding affinity for all 15 urea-anion complexes under the influence of solvent environment were examined using the IEF-PCM continuum solvation model. Although the binding affinities are weakened substantially because of solvent effect, these drastic changes do not affect the affinity order in the gas phase. The experimentally observed affinity strength in chloroform, Cl > NO(3) > 4 Br , was confirmed by this work. Moreover, we found a high correlation between Delta E(bind) (1) and Delta E(In) (1,3-dimethylurea) for all three binding modes, implying that the affinity strength of 1 to these five anions is determined mainly by the proton-accepting ability of anions, not by steric effect.
关键词Selective Anion Complexation Sulfate-binding Protein Solvation Free-energy Ief-pcm Model Ab-initio Dissociation-constants Conformational Control Successive Residues Crystal-structures Monovalent Anions
资助信息National Natural Science Foundations of China[30725048, 20763007, U1032602, 91013002]; National Basic Research Program of China[2009 CB522300]; Science and Technology Department of Yunnan Province[2008OC011, 2006B0081M]; Chinese Academy of Sciences[KSCX2-YW-R177]; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences
学科领域Chemistry ; Physics
收录类别sci
语种英语
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/14469
专题植物化学与西部植物资源持续利用国家重点实验室
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Chen, YS,Pan, XL,Yan, H,et al. Multiple hydrogen-bonding interactions between macrocyclic triurea and F(-), Cl(-), Br(-), I(-) and NO(3)(-): a theoretical investigation[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS,2011,13(16):7384-7395.
APA Chen, YS,Pan, XL,Yan, H,&Tan, NH.(2011).Multiple hydrogen-bonding interactions between macrocyclic triurea and F(-), Cl(-), Br(-), I(-) and NO(3)(-): a theoretical investigation.PHYSICAL CHEMISTRY CHEMICAL PHYSICS,13(16),7384-7395.
MLA Chen, YS,et al."Multiple hydrogen-bonding interactions between macrocyclic triurea and F(-), Cl(-), Br(-), I(-) and NO(3)(-): a theoretical investigation".PHYSICAL CHEMISTRY CHEMICAL PHYSICS 13.16(2011):7384-7395.
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