Impact of long-range van der Waals forces on chiral recognition in a Cinchona alkaloid chiral selector system
文献信息
Petr Milko, Jana Roithová, Kevin A. Schug, Karel Lemr
Singly-charged complexes of (8S,9R)-tert-butylcarbamoylquinine (tBuCQN), N-3,5-dinitrobenzoyl-(S,R)-leucine (DNB-S/R-leucine), and alkali metal counter ions (Li+, Na+, K+) were investigated by density-functional theory. It is shown that the cations prefer formation of an ionic pair with the carboxylate group of DNB-Leu over the formation of a cation–π interaction. The [tBuCQN·DNB-S/R-Leu·Na]+ complex is bound by a Coulombic attraction, a hydrogen bond, a π−π interaction and van der Waals forces. The tBuCQN chiral selector preferentially complexes with the DNB-S-Leu enantiomer, because the favourable stereochemistry allows the stabilization of the complex by at least one binding mode more compared to the complex containing the DNB-R-Leu molecule. Weakening of the binding modes is observed using the lithium counter ion compared to the sodium one. The weakening is more pronounced in [tBuCQN·DNB-R-Leu·Li]+ than in [tBuCQN·DNB-S-Leu·Li]+. The exact opposite effect is observed using the potassium counter ion. Hence, the lithium counter ion enhances the enantioselectivity of tBuCQN while the potassium counter ion reduces the enantioselectivity of tBuCQN.
相关文献
Evaluation of partial least-squares with second-order advantage for the multi-way spectroscopic analysis of complex biological samples in the presence of analyte–background interactions
María J. Culzoni, Héctor C. Goicoechea, Ariana P. Pagani, Miguel A. Cabezón, Alejandro C. Olivieri
DOI: 10.1039/B603383K
NMR-based screening: a powerful tool in fragment-based drug discovery
Murray Coles
DOI: 10.1039/B709658P
A fuzzy distance metric for measuring the dissimilarity of planar chromatographic profiles with application to denaturing gradient gel electrophoresis data from human skin microbes: demonstration of an individual and gender-based fingerprint
Yun Xu, Richard G. Brereton, Karlheinz Trebesius, Ingrid Bergmaier, Elisabeth Oberzaucher, Karl Grammer, Dustin J. Penn
DOI: 10.1039/B702410J
Modified secured principal component regression for detection of unexpected chromatographic features in herbal fingerprints
Yun Hu, Yi-Zeng Liang, Pei-Shan Xie, Yukihiro Ozaki
DOI: 10.1039/B513365C
Distinction of malignant melanoma and epidermis using IR micro-spectroscopy and statistical methods
Z. Hammody, S. Argov, R. K. Sahu, E. Cagnano, R. Moreh, S. Mordechai
DOI: 10.1039/B712040K
Enhanced stability and sensitivity of ionic liquid–carbon paste electrodes at elevated temperatures
Mustafa M. Musameh, Roohollah Torabi Kachoosangi, Richard G. Compton
DOI: 10.1039/B713071F
A turn-on fluorescent sensor for zinc and cadmium ions based on perylene tetracarboxylic diimide
Xiangjun Liu, Dihua Shangguan
DOI: 10.1039/C2AN36203A
Novel 15-crown-5 ether or β-diketone incorporated gadolinium complexes for the detection of potassium ions or magnesium and calcium ions
Hiroki Hifumi, Akihiro Tanimoto, Daniel Citterio, Hirokazu Komatsu, Koji Suzuki
DOI: 10.1039/B707225B
您可能还喜欢
什么是5-Fluoro-4-iodo-2-methylaniline(CAS号:307306-08-7)?
5-氟-4-碘-2-甲氨基苯属于芳香族化合物,其分子式为C8H7FN2I。该化合物具有一定的反应活性,在有机合成和药物化学领域有一定的应用。
4-氟-3-硝基三氟甲苯(CAS号:367-86-2)通常如何合成?
4-氟-3-硝基三氟甲苯通常通过将三氟甲基苯在酸性条件下催化氧化为三氟甲基硝基苯,然后进行氟化反应得到目标化合物。该过程需要使用催化剂,如三氟乙酸,反应产率较高...
6-氯-9-(2,3,5-三苯甲酰氧基-2-C-甲基-beta-D-呋喃核糖基)-9H-嘌呤(CAS号:205171-05-7)的物理化学性质是什么?
该化合物为白色至类白色晶体,分子量约为1046.95。它在水中几乎不溶,在有机溶剂如乙腈和甲醇中具有一定的溶解性。该化合物具有良好的化学稳定性和生物活性。
如何储存6-氟喹啉-4-羧酸(CAS号:220844-73-5)?
6-氟喹啉-4-羧酸应储存在阴凉、干燥、通风良好的地方,避免阳光直射。储存在密闭容器中,避免与空气中的水分接触。储存温度应控制在室温以下,避免高温。
(2S,2'S,3S,3'S)-3,3'-di-tert-butyl-4,4'-bis(2,6-dimethoxyphenyl)-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole(CAS号:1435940-21-8)通常如何合成?
该化合物通常通过芳香族化合物的亲核取代反应合成,首先将2,6-二甲氧基苯基引入到双环结构中,然后通过特定条件下的还原或氧化反应引入二叔丁基。反应过程中使用了钯作...
如何储存KY02111(CAS号:1118807-13-8)?
KY02111应储存于阴凉、干燥、通风良好的地方,避免阳光直射和高温环境。应使用合适的密闭容器储存,并确保容器密封良好,防止水分和潮气进入。在储存期间,应注意检...
如何储存4-(4-氯苯氧基)丁酸乙酯(CAS号:59227-79-1)?
4-(4-氯苯氧基)丁酸乙酯应储存在阴凉、干燥、通风良好的地方,远离火源和热源。避免阳光直射,防止容器破裂导致泄漏。储存时应保持容器密封,避免与空气中的水蒸气接...
4-庚基苯乙酮(CAS号:37593-03-6)安全吗?
4-庚基苯乙酮相对安全,但在使用和储存时仍需注意。应避免吸入其蒸气,避免皮肤接触,使用时需佩戴防护眼镜和手套。储存时应远离火源和热源,保持容器密封,放置于阴凉、...
什么是乙基2-氨基-4-(3-溴苯基)噻吩-3-羧酸乙酯(CAS号:438218-48-5)?
乙基2-氨基-4-(3-溴苯基)噻吩-3-羧酸乙酯是一种有机化合物,分子式为C16H12BrN2O2S。它是一种含有噻吩环、氨基、溴苯基和羧酸酯结构的化合物。这...
什么是(9ci)-2-氨基-6-甲基-苯甲酰胺(CAS号:1885-31-0)?
(9ci)-2-氨基-6-甲基-苯甲酰胺是一种化学化合物,其英文名称为2-Amino-6-methylbenzamide,CAS号为1885-31-0。该化合物...
来源期刊
Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.













![2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol structure 2,2'-{2,2-Propanediylbis[(2,6-dibromo-4,1-phenylene)oxy]}diethanol structure](https://cnstatic.chemtradehub.com/structs/416/4162-45-2-b3d6.webp)
