Halide anion capture and recognition by a tetrahedral tetraammonium receptor in water: A molecular dynamics investigation

被引:12
|
作者
Chaumont, A [1 ]
Engler, E [1 ]
Wipff, G [1 ]
机构
[1] Inst Chim, Lab MSM, F-67000 Strasbourg, France
关键词
anions; macrocyclic chemistry; molecular dynamics; molecular recognition;
D O I
10.1002/chem.200390068
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report molecular dynamics potential of mean force (PMF) simulations on the capture of halide anions X- (F-, Cl-, Br-) by a tetrahedral receptor L4+ built from four quaternary ammonium sites connected by six (CH2)(n) chains, leading to the formation of inclusion complexes X- C L4+. Simulations performed with a reaction field correction of the electrostatics and with PME-Ewald summation gave very similar energy profiles. In aqueous solution, an energy barrier of 12-17 kcal mol(-1) was found for the three anions, mainly due to their dehydration when they enter through the largest triangular face of L4+. In the inclusion complexes, the anion is anchored near the center of the cavity due to the electrostatic field of the four positively charged ammonium sites, shielded from the surrounding water molecules. It was predicted that L4+ is selective for Cl- over Br- which both form stable inclusion complexes, while the F- complex should dissociate. The comparison of PMFs in aqueous solution and in the gas phase and the energy component analysis demonstrates the importance of solvent on the nature of these complexes and on the complexation energy profiles. The Cl-/Br- selectivity obtained from the dissociation pathways in water was in good agreement with the results of free energy perturbation simulations based on the "alchemical route" of a thermodynamic cycle, and consistent with experimental observations.
引用
收藏
页码:635 / 643
页数:9
相关论文
共 50 条
  • [21] Investigation of the mechanism of chiral recognition by molecular micelles with molecular dynamics simulations
    Zack, Stephanie
    Billiot, Eugene
    Billiot, Fereshteh
    Fang, Yayin
    Morris, Kevin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [22] Receptor Dynamics in Molecular Recognition by Cryo-EM and Molecular Simulation
    Zhao, Yizhen
    Wang, He
    Zang, Yongjian
    Zhu, Xun
    Zhang, Shengli
    Zhang, Lei
    COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2021, 24 (10) : 1696 - 1701
  • [23] Ab initio molecular dynamics study of halide water clusters.
    Nguyen, QH
    Kuo, IFW
    Tobias, DJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U330 - U330
  • [24] Do Molecular Dynamics Force Fields Capture Conformational Dynamics of Alanine in Water?
    Zhang, Shuting
    Schweitzer-Stenner, Reinhard
    Urbanc, Brigita
    JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2020, 16 (01) : 510 - 527
  • [25] Molecular dynamics investigation of benzene in supercritical water
    Zhou, J
    Wang, WC
    Zhong, CL
    CHINESE JOURNAL OF CHEMICAL ENGINEERING, 2001, 9 (02) : 196 - 199
  • [26] Molecular Dynamics Investigation of Benzene in Supercritical Water
    周健
    汪文川
    仲崇立
    Chinese Journal of Chemical Engineering, 2001, (02) : 78 - 81
  • [27] MOLECULAR RECOGNITION - ANION CRYPTATES OF A MACROBICYCLIC RECEPTOR MOLECULE FOR LINEAR TRIATOMIC SPECIES
    LEHN, JM
    SONVEAUX, E
    WILLARD, AK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (15) : 4914 - 4916
  • [28] Molecular recognition of fluoride anion: Benzene-based tripodal imidazolium receptor
    Yun, S
    Ihm, H
    Kim, HG
    Lee, CW
    Indrajit, B
    Oh, KS
    Gong, YJ
    Lee, JW
    Yoon, J
    Lee, HC
    Kim, KS
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06): : 2467 - 2470
  • [29] Ab initio molecular dynamics studies of halide-water clusters.
    Nguyen, QH
    Kuo, IF
    Tobias, DJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U273 - U273
  • [30] Molecular dynamics simulations of alkali halide adsorption to water-alumina interfaces
    Wang, Ruiyu
    Millan, Kevin
    Remsing, Richard
    Piontek, Stefan
    Tuladhar, Aashish
    Magidson, Leah
    Carnevale, Vincenzo
    Klein, Michael
    Borguet, Eric
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254