Статті в журналах: "Hydrogen-Bonding Catalysis"

1

R0UHI, MAUREEN. "CATALYSIS BY HYDROGEN BONDING." Chemical & Engineering News Archive 81, no. 28 (July 14, 2003): 13. http://dx.doi.org/10.1021/cen-v081n028.p013a.

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2

Kaneko, Shiho, Yusuke Kumatabara, Shoichi Shimizu, Keiji Maruoka, and Seiji Shirakawa. "Hydrogen-bonding catalysis of sulfonium salts." Chemical Communications 53, no. 1 (2017): 119–22. http://dx.doi.org/10.1039/c6cc08411g.

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3

Grotjahn, Douglas B. "Heteroatoms moving protons: Synthetic and mechanistic studies of bifunctional organometallic catalysis." Pure and Applied Chemistry 82, no. 3 (February 14, 2010): 635–47. http://dx.doi.org/10.1351/pac-con-09-10-31.

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Improved organometallic catalysts resulting from including ligands capable of proton transfer or hydrogen bonding are described. Pyridyl- and imidazolylphosphines accelerate anti-Markovnikov alkyne hydration and alkene isomerization and deuteration by factors of 1000 to more than 10 000. Evidence for proton transfer and hydrogen bonding in catalytic intermediates comes from computational, mechanistic, and structural studies, where 15N NMR data are particularly revealing.

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4

Mote, Nilesh R., and Samir H. Chikkali. "Hydrogen-Bonding-Assisted Supramolecular Metal Catalysis." Chemistry - An Asian Journal 13, no. 23 (November 20, 2018): 3623–46. http://dx.doi.org/10.1002/asia.201801302.

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5

Guo, Hong, and Dennis R. Salahub. "Cooperative Hydrogen Bonding and Enzyme Catalysis." Angewandte Chemie International Edition 37, no. 21 (November 16, 1998): 2985–90. http://dx.doi.org/10.1002/(sici)1521-3773(19981116)37:21<2985::aid-anie2985>3.0.co;2-8.

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6

Yin, Yanli, Xiaowei Zhao, Baokun Qiao, and Zhiyong Jiang. "Cooperative photoredox and chiral hydrogen-bonding catalysis." Organic Chemistry Frontiers 7, no. 10 (2020): 1283–96. http://dx.doi.org/10.1039/d0qo00276c.

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Chiral hydrogen-bonding catalysis is a classic strategy in asymmetric organocatalysis. Recently, it has been used to cooperate with photoredox catalysis, becoming a powerful tool to access optical pure compounds via radical-based transformations.

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7

Nishikawa, Yasuhiro. "Recent topics in dual hydrogen bonding catalysis." Tetrahedron Letters 59, no. 3 (January 2018): 216–23. http://dx.doi.org/10.1016/j.tetlet.2017.12.037.

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8

Tran, Ngon T., Sean O. Wilson, and Annaliese K. Franz. "Cooperative Hydrogen-Bonding Effects in Silanediol Catalysis." Organic Letters 14, no. 1 (December 7, 2011): 186–89. http://dx.doi.org/10.1021/ol202971m.

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9

Nakamura, Takumi, Ken Okuno, Ryuichi Nishiyori, and Seiji Shirakawa. "Hydrogen‐Bonding Catalysis of Alkyl‐Onium Salts." Chemistry – An Asian Journal 15, no. 4 (January 23, 2020): 463–72. http://dx.doi.org/10.1002/asia.201901652.

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10

Reyes, Efraím, Liher Prieto, Uxue Uria, Luisa Carrillo, and Jose L. Vicario. "Asymmetric Dual Enamine Catalysis/Hydrogen Bonding Activation." Catalysts 13, no. 7 (July 11, 2023): 1091. http://dx.doi.org/10.3390/catal13071091.

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Asymmetric enamine base activation of carbonyl compounds is a well-known and widely used strategy for providing functionalization of organic compounds in an efficient way. The use of solely organic substances, which in most cases are commercially available primary or secondary amines that are easy to obtain, avoids the use of hazardous substances or metal traces, making this type of catalysis a highly convenient methodology from a sustainable point of view. In many cases, the reactivity or the stereoselectivity obtained is far from being a practical and advantageous strategy; this can be improved by using a hydrogen bonding co-catalyst that can help during the activation of one species or by using a bifunctional catalyst that can direct the approximation of reagents during the reaction outcome. In this review, we describe the most efficient methodologies that make use of a dual activation of reagents for performing α-functionalization (enamine activation) or remote functionalization (such as dienamine or trienamine activation) of carbonyl compounds.

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11

Huang, Chiu-Ping, Meng-Che Tsai, Xiao-Ming Wang, Hao-Sheng Cheng, Yu-Hsiang Mao, Chun-Jern Pan, Jiunn-Nan Lin, et al. "Engineering heterometallic bonding in bimetallic electrocatalysts: towards optimized hydrogen oxidation and evolution reactions." Catalysis Science & Technology 10, no. 3 (2020): 893–903. http://dx.doi.org/10.1039/c9cy02181g.

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12

Mammadova, Flora, Büşra Hamarat, Dilgam Ahmadli, Onur Şahin, Uğur Bozkaya, and Yunus E. Türkmen. "Polarization‐Enhanced Hydrogen Bonding in 1,8‐Dihydroxynaphthalene: Conformational Analysis, Binding Studies and Hydrogen Bonding Catalysis." ChemistrySelect 5, no. 42 (November 13, 2020): 13387–96. http://dx.doi.org/10.1002/slct.202002960.

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13

Breugst, Martin, Daniel von der Heiden та Julie Schmauck. "Novel Noncovalent Interactions in Catalysis: A Focus on Halogen, Chalcogen, and Anion-π Bonding". Synthesis 49, № 15 (23 травня 2017): 3224–36. http://dx.doi.org/10.1055/s-0036-1588838.

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Анотація:

Noncovalent interactions play an important role in many biological and chemical processes. Among these, hydrogen bonding is very well studied and is already routinely used in organocatalysis. This Short Review focuses on three other types of promising noncovalent interactions. Halogen bonding, chalcogen bonding, and anion-π bonding have been introduced into organocatalysis in the last few years and could become important alternate modes of activation to hydrogen bonding in the future.1 Introduction2 Halogen Bonding3 Chalcogen Bonding4 Anion-π Bonding5 Conclusions

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14

Breit, Bernhard. "Catalysts through self-assembly for combinatorial homogeneous catalysis." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 855–60. http://dx.doi.org/10.1351/pac200880050855.

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Inspired by the principle of DNA base-pairing, a new concept for the self-assembly of molecular catalysts is described herein. Thus, employing A-T analogous complementary hydrogen-bonding templates, self-assembly of monodentate to bidentate ligands in the coordination sphere of a transition-metal salt occurs to give defined self-assembly catalysts. This approach is intrinsically combinatorial and allows the facile generation of defined catalyst libraries through simple component mixing. From the study of these ligand libraries, excellent catalysts for linear-selective hydroformylation, asymmetric hydrogenation, and anti-Markovnikov hydration of terminal alkynes have emerged.

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15

Prins, Leonard J., David N. Reinhoudt, and Peter Timmerman. "Noncovalent Synthesis Using Hydrogen Bonding." Angewandte Chemie International Edition 40, no. 13 (July 2, 2001): 2382–426. http://dx.doi.org/10.1002/1521-3773(20010702)40:13<2382::aid-anie2382>3.0.co;2-g.

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16

Nedrud, David M., Hui Lin, Gilsinia Lopez, Santosh K. Padhi, Graig A. Legatt та Romas J. Kazlauskas. "Uncovering divergent evolution of α/β-hydrolases: a surprising residue substitution needed to convert Hevea brasiliensis hydroxynitrile lyase into an esterase". Chem. Sci. 5, № 11 (2014): 4265–77. http://dx.doi.org/10.1039/c4sc01544d.

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17

Liu, Shixuan, Shuang Li, Guomin Shen, Narayanasami Sukumar, Andrzej M. Krezel, and Weikai Li. "Structural basis of antagonizing the vitamin K catalytic cycle for anticoagulation." Science 371, no. 6524 (November 5, 2020): eabc5667. http://dx.doi.org/10.1126/science.abc5667.

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Vitamin K antagonists are widely used anticoagulants that target vitamin K epoxide reductases (VKOR), a family of integral membrane enzymes. To elucidate their catalytic cycle and inhibitory mechanism, we report 11 x-ray crystal structures of human VKOR and pufferfish VKOR-like, with substrates and antagonists in different redox states. Substrates entering the active site in a partially oxidized state form cysteine adducts that induce an open-to-closed conformational change, triggering reduction. Binding and catalysis are facilitated by hydrogen-bonding interactions in a hydrophobic pocket. The antagonists bind specifically to the same hydrogen-bonding residues and induce a similar closed conformation. Thus, vitamin K antagonists act through mimicking the key interactions and conformational changes required for the VKOR catalytic cycle.

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18

Corradi, Eleonora, Stefano V. Meille, Maria T. Messina, Pierangelo Metrangolo, and Giuseppe Resnati. "Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes." Angewandte Chemie International Edition 39, no. 10 (May 15, 2000): 1782–86. http://dx.doi.org/10.1002/(sici)1521-3773(20000515)39:10<1782::aid-anie1782>3.0.co;2-5.

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19

Pupo, Gabriele, Francesco Ibba, David M. H. Ascough, Anna Chiara Vicini, Paolo Ricci, Kirsten E. Christensen, Lukas Pfeifer, et al. "Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis." Science 360, no. 6389 (May 10, 2018): 638–42. http://dx.doi.org/10.1126/science.aar7941.

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20

Ohsaki, Koji, Katsuaki Konishi, and Takuzo Aida. "Supramolecular acid/base catalysis via multiple hydrogen bonding interaction." Chemical Communications, no. 16 (July 8, 2002): 1690–91. http://dx.doi.org/10.1039/b202970g.

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21

Wang, Weibo, Manish Kumar, Gerald B. Hammond, and Bo Xu. "Enhanced Reactivity in Homogeneous Gold Catalysis through Hydrogen Bonding." Organic Letters 16, no. 2 (January 6, 2014): 636–39. http://dx.doi.org/10.1021/ol403584e.

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22

Wells, Tim N. C., and Alan R. Fersht. "Hydrogen bonding in enzymatic catalysis analysed by protein engineering." Nature 316, no. 6029 (August 1985): 656–57. http://dx.doi.org/10.1038/316656a0.

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23

Han, Junbin, Zhichao Lu, Andrew L. Flach, Robert S. Paton, Gerald B. Hammond, and Bo Xu. "Role of Hydrogen-Bonding Acceptors in Organo-Enamine Catalysis." Chemistry - A European Journal 21, no. 33 (July 15, 2015): 11687–91. http://dx.doi.org/10.1002/chem.201502407.

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24

Sánchez, Luis, Nazario Martín, and Dirk M. Guldi. "Hydrogen-Bonding Motifs in Fullerene Chemistry." Angewandte Chemie International Edition 44, no. 34 (August 26, 2005): 5374–82. http://dx.doi.org/10.1002/anie.200500321.

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25

Cordones-Hahn, Amy. "(Invited) Excited States and Reaction Mechanisms of Catalysts with Redox Active Ligands Investigated with X-Ray Spectroscopy." ECS Meeting Abstracts MA2022-02, no. 48 (October 9, 2022): 1834. http://dx.doi.org/10.1149/ma2022-02481834mtgabs.

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Metal dithiolenes and related molecular catalysts known for their redox-active ligands and their efficient and robust electro- and photo-catalysis of the hydrogen evolution reaction are investigated. To understand how the redox-active ligands of these catalysts influence their electronic excited states and participate in their chemical reactions, we need element-specific probes of charge and bonding at both metal and ligand atomic sites. X-ray absorption spectroscopy (XAS) affords us this opportunity and is used to study the electro- and photo-catalytic reaction mechanisms of these complexes, with a specific focus on the role of metal versus ligand atomic sites. Steady-state and time-resolved XAS studies at the Ni and S K-edges will be presented to identify the redox activity of metal vs. ligand sites on timescales spanning from the ultrafast excited state relaxation and photochemical activation processes to the steady-state creation of important intermediates in the multi-step hydrogen evolution reaction.

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26

Zhang, Yirui, Tao Wang, Botao Huang, and Yang Shao-Horn. "(Invited) Controlling Hydrogen Evolution and Oxygen Reduction Electrocatalysis By Tuning Interfacial Hydrogen Bonds." ECS Meeting Abstracts MA2022-02, no. 49 (October 9, 2022): 1894. http://dx.doi.org/10.1149/ma2022-02491894mtgabs.

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Designing electrochemical water splitting and its reverse process is crucial for fuel cells to achieve high efficiency. Conventional design of catalysts has focused on tuning the surface electronic structures and binding strength of intermediates, while recent studies show that changing electrolyte compositions, such as cations and pH [1], can also significantly alter catalytic activity, highlighting new opportunities in tuning noncovalent interactions in the electrolytes to control activities. In the first part of this talk, we use an interfacial layer of protic ionic liquids on platinum and gold to tune the oxygen-reduction reaction (ORR) kinetics, where altering the proton activity of ionic liquids increases the intrinsic ORR activity by up to five times [2]. The maximum enhancement of kinetics is achieved when the pKa of the ionic liquid is comparable to that of the reaction intermediate, which is attributed to the most strengthened hydrogen bonding between the ionic liquid and ORR products, as supported by surface-enhanced infrared absorption spectroscopy (SEIRAS). In the second part, we confine water in an organic matrix and tune the hydrogen-bonding networks as well as hydrogen evolution and oxidation reactions (HER/HOR) kinetics by changing the water concentration (1% - 50% molar ratio) and altering the physical properties (donor number) of organic solvents. Decreasing the water-to-organic ratio, the OH stretching frequency of water shifts to higher wavenumbers, indicating more isolated water, while the water reduction has more negative onset potentials. The shifts in onset potentials are solvent-dependent, highlighting the role of interfacial hydrogen bonds between solvents and water in controlling HER/HOR kinetics. SEIRAS measurements provide further support to the changes in interfacial hydrogen bonding during the reactions. These findings open up immense opportunities for using noncovalent hydrogen bonding interactions at the electrified interface to control the kinetics of ORR, HER, and beyond. The understanding would also be impactful across other reactions crucial to improving decarbonizing efforts in energy storage, such as CO2 reduction and aqueous batteries. References [1] Huang, B., Rao, R.R., You, S., Hpone Myint, K., Song, Y., Wang, Y., Ding, W., Giordano, L., Zhang, Y., Wang, T. and Muy, S., 2021. Cation-and pH-Dependent Hydrogen Evolution and Oxidation Reaction Kinetics. JACS Au, 1(10), pp.1674-1687. [2] Wang, T. ‡, Zhang, Y. ‡, Huang, B., Cai, B., Rao, R.R., Giordano, L., Sun, S.G. and Shao-Horn, Y., 2021. Enhancing oxygen reduction electrocatalysis by tuning interfacial hydrogen bonds. Nature Catalysis, 4(9), pp.753-762.

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27

Marquis, Eric, Jérôme Graton, Michel Berthelot, Aurélien Planchat та Christian Laurence. "Liaison hydrogène des arylamines : compétition des sites π et N". Canadian Journal of Chemistry 82, № 9 (1 вересня 2004): 1413–22. http://dx.doi.org/10.1139/v04-128.

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An IR study, in the region of OH stretching, of a reference hydrogen-bond donor, 4-fluorophenol, hydrogen bonded to primary, secondary, and tertiary arylamines differently substituted on the ring and on the nitrogen, shows the formation of two kinds of 1:1 complexes in CCl4 solution: an OH···π and an OH···N hydrogen-bonded complex. The IR method gives only access to a global complexation constant Kt. A method is proposed for separating Kt into a Kπ component for hydrogen bonding to the π system and a KN component for hydrogen bonding to the nitrogen atom. This method is validated by comparing the estimated Kπ and KN values to theoretically calculated descriptors of basicity: the nitrogen lone pair orientation towards the aromatic ring, the molecular electrostatic potentials around the nitrogen and the π cloud, and the enthalpy of hydrogen bonding of hydrogen fluoride with the π system of selected arylamines. The main electronic and steric factors governing the competition between π and N sites are analysed. The strongest π and N bases among the arylamines are julolidine and Tröger's base, respectively. Triphenylamine and diphenylamine, which are nitrogen Brønsted bases, become π bases in hydrogen bonding. Moreover, there is no correlation between the pKHB and the pKBH+ scales of basicity of arylamines. The use of the pKBH+ scale is therefore not recommended in hydrogen-bonding studies.Key words: hydrogen bonding, arylamines, pKHB scale, competition of π and N hydrogen-bonded sites.

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28

Bencivenni, Grazia, Nathalie Saraiva Rosa, Paolo Grieco, Malachi W. Gillick-Healy, Brian G. Kelly, Brendan Twamley, and Mauro F. A. Adamo. "Quaternary Ammonium Salts Interact with Enolates and Sulfonates via Formation of Multiple +N-C-H Hydrogen Bonding Interactions." Catalysts 12, no. 7 (July 21, 2022): 803. http://dx.doi.org/10.3390/catal12070803.

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We report herein sharp physical evidence, i.e., single-crystal X-ray diffraction and 1H-NMR spectral data, confirming that quaternary ammonium species interact with anions via a set of directional ion–dipole cooperative +N-C-H unusual H-bonding interactions and not via pure non-directional ionic electrostatic interactions. This finding, which has been often invoked by calculations, is herein substantiated by the preparation of two model compounds and an analysis of their X-ray crystal structures in the solid state and 1H-NMR spectra in solution. These observations are particularly pertinent for the rational design of novel catalyses and catalysts and providing guidance to an understanding of these species in solution and during asymmetric enantioselective catalysis.

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29

Wang, Hongyu. "Chiral Phase-Transfer Catalysts with Hydrogen Bond: A Powerful Tool in the Asymmetric Synthesis." Catalysts 9, no. 3 (March 7, 2019): 244. http://dx.doi.org/10.3390/catal9030244.

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Asymmetric phase-transfer catalysis has been widely applied into organic synthesis for efficiently creating chiral functional molecules. In the past decades, chiral phase-transfer catalysts with proton donating groups are emerging as an extremely significant strategy in the design of novel catalysts, and a large number of enantioselective reactions have been developed. In particular, the proton donating groups including phenol, amide, and (thio)-urea exhibited unique properties for cooperating with the phase-transfer catalysts, and great advances on this field have been made in the past few years. This review summarizes the seminal works on the design, synthesis, and applications of chiral phase-transfer catalysts with strong hydrogen bonding interactions.

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30

Reddi, Ravikumar, Kiran Kumar Singarapu, Debnath Pal, and Anthony Addlagatta. "The unique functional role of the C–H⋯S hydrogen bond in the substrate specificity and enzyme catalysis of type 1 methionine aminopeptidase." Molecular BioSystems 12, no. 8 (2016): 2408–16. http://dx.doi.org/10.1039/c6mb00259e.

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Unique C–H⋯S hydrogen bonding interactions allow nature to attain recognition specificity between molecular interfaces where there is no apparent scope for classical hydrogen bonding or polar interactions.

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31

Li, Kaixin, Limin Deng, Shun Yi, Yabo Wu, Guangjie Xia, Jun Zhao, Dong LU, and Yonggang Min. "Boosting the performance by the water solvation shell with hydrogen bonds on protonic ionic liquids: insights into the acid catalysis of the glycosidic bond." Catalysis Science & Technology 11, no. 10 (2021): 3527–38. http://dx.doi.org/10.1039/d0cy02459g.

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32

Ionova, Violetta, Anton Abel, Alexei Averin, and Irina Beletskaya. "Heterobinuclear Metallocomplexes as Photocatalysts in Organic Synthesis." Catalysts 13, no. 4 (April 18, 2023): 768. http://dx.doi.org/10.3390/catal13040768.

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Photocatalytic processes under visible light have constantly been finding more and more applications in organic synthesis as they allow a wide range of transformations to proceed under mild conditions. The combination of photoredox catalysis with metal complex catalysis gives an opportunity to employ the advantages of these two methodologies. Covalent bonding of photocatalyst and metal complex catalyst using bridging ligands increases the efficiency of the electron and energy transfer between these two parts of the catalyst, leading to more efficient and selective catalytic systems. Up to now, after numerous investigations of the photocatalytic reduction of CO2 and hydrogen generation, such a strategy was firmly established to substantially increase the catalyst’s activity. This review is aimed at the achievements and perspectives in the field of design and application of heterobinuclear metal complexes as photocatalysts in organic synthesis.

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33

Xu, Yueting, Yanfei Zhao, Fengtao Zhang, Yuepeng Wang, Ruipeng Li, Junfeng Xiang, and Zhimin Liu. "Hydrogen bonding-catalysed alcoholysis of propylene oxide at room temperature." Chemical Communications 57, no. 70 (2021): 8734–37. http://dx.doi.org/10.1039/d1cc03602e.

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Alcoholysis of propylene oxide is achieved over azolate ionic liquids at room temperature by hydrogen-bonding catalysis, accessing glycol ethers in moderate to high yields with selectivity of >99%.

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34

Raczyńska, Ewa D., Christian Laurence, and Michel Berthelot. "Basicité de liaison hydrogène de formamidines substituées sur l'azote imino." Canadian Journal of Chemistry 70, no. 8 (August 1, 1992): 2203–8. http://dx.doi.org/10.1139/v92-276.

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The basicity of the hydrogen bonds of formamidines 1–19 was measured by means of the formation constant KHB of their complexes with p-fluorophenol and the frequency shift Δν(OH) of methanol hydrogen-bonded to 1–19. The study of the ν(C=N) band shows that hydrogen bonding takes place with the imino nitrogen atom. On the hydrogen-bonding basicity scale, the formamidines appear to be more basic than the corresponding amides and pyridines, and as basic as the imidazoles. The field effect of electron-withdrawing substituents and the steric effect of bulky alkyl groups on the imino nitrogen atom markedly decrease the hydrogen-bonding basicity.

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35

EIS, Christian, and Bernd NIDETZKY. "Substrate-binding recognition and specificity of trehalose phosphorylase from Schizophyllum commune examined in steady-state kinetic studies with deoxy and deoxyfluoro substrate analogues and inhibitors." Biochemical Journal 363, no. 2 (April 8, 2002): 335–40. http://dx.doi.org/10.1042/bj3630335.

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Trehalose phosphorylase is a component of the α-d-glucopyranosyl α-d-glucopyranoside (α,α-trehalose)-degrading enzyme system in fungi and it catalyses glucosyl transfer from α,α-trehalose to phosphate with net retention of the anomeric configuration. The enzyme active site has no detectable affinity for α,α-trehalose in the absence of bound phosphate and catalysis occurs from the ternary complex. To examine the role of non-covalent enzyme—substrate interactions for trehalose phosphorylase recognition, we used the purified enzyme from Schizophyllum commune and tested a series of incompetent structural analogues of the natural substrates and products as inhibitors of the enzyme. Equilibrium-binding constants (Ki) for deoxy- and deoxyfluoro derivatives of d-glucose show that loss of interactions with the 3-, 4- or 6-OH, but not the reactive 1- and the 2-OH, results in considerably (≥100-fold) weaker affinity for sugar-binding subsite +1, revealing the requirement for hydrogen bonding with hydroxyls, away from the site of chemical transformation to position precisely the d-glucose-leaving group/nucleophile for catalysis. The high specificity of trehalose phosphorylase for the sugar aglycon during binding and conversion of O-glycosides is in contrast with the observed α-retaining phosphorolysis of α-d-glucose-1-fluoride (α-d-Glc-1-F) since the productive bonding capability of the fluoride-leaving group with subsite +1 is minimal. The specificity constant (19M−1·s−1) and catalytic-centre activity (0.1s−1) for the reaction with α-d-Glc-1-F are 0.10- and 0.008-fold the corresponding kinetic parameters for the enzymic reaction with α,α-trehalose. The non-selective-inhibition profile for a series of inactive α-d-glycopyranosyl phosphates shows that the driving force for the binary-complex formation lies mainly in interactions of the enzyme with the phosphate group and suggests that hydrogen bonding with hydroxyl groups at the catalytic site (subsite −1) contributes to catalysis by providing stabilization, which is specific to the transition state. Vanadate, a tight-binding phosphate mimic, inhibits the phosphorolysis of α-d-Glc-1-F by forming a ternary complex whose apparent dissociation constant of 120μM is approx. 160-fold greater than the dissociation constant of the same inhibitor complex with α,α-trehalose.

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36

Lai, Chih-Hsuan, Co-Chih Chang, Huai-Chia Chuang, Tse-Hua Tan, and Ping-Chiang Lyu. "Structural Insights into the Active Site Formation of DUSP22 in N-loop-containing Protein Tyrosine Phosphatases." International Journal of Molecular Sciences 21, no. 20 (October 12, 2020): 7515. http://dx.doi.org/10.3390/ijms21207515.

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Анотація:

Cysteine-based protein tyrosine phosphatases (Cys-based PTPs) perform dephosphorylation to regulate signaling pathways in cellular responses. The hydrogen bonding network in their active site plays an important conformational role and supports the phosphatase activity. Nearly half of dual-specificity phosphatases (DUSPs) use three conserved residues, including aspartate in the D-loop, serine in the P-loop, and asparagine in the N-loop, to form the hydrogen bonding network, the D-, P-, N-triloop interaction (DPN–triloop interaction). In this study, DUSP22 is used to investigate the importance of the DPN–triloop interaction in active site formation. Alanine mutations and somatic mutations of the conserved residues, D57, S93, and N128 substantially decrease catalytic efficiency (kcat/KM) by more than 102-fold. Structural studies by NMR and crystallography reveal that each residue can perturb the three loops and induce conformational changes, indicating that the hydrogen bonding network aligns the residues in the correct positions for substrate interaction and catalysis. Studying the DPN–triloop interaction reveals the mechanism maintaining phosphatase activity in N-loop-containing PTPs and provides a foundation for further investigation of active site formation in different members of this protein class.

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37

Venkatesan, Pushpa, Yuan Cheng, and Daniel Kahne. "Hydrogen Bonding in Micelle Formation." Journal of the American Chemical Society 116, no. 15 (July 1994): 6955–56. http://dx.doi.org/10.1021/ja00094a068.

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Wu, Fengtian, Yanfei Zhao, Yuepeng Wang, Yueting Xu, Minhao Tang, Zhenpeng Wang, Buxing Han, and Zhimin Liu. "Hydrogen-bonding and acid cooperative catalysis for benzylation of arenes with benzyl alcohols over ionic liquids." Green Chemistry 24, no. 8 (2022): 3137–42. http://dx.doi.org/10.1039/d1gc04485k.

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39

Greener, Bryan, Stephen J Archibald, and Michael Hodkinson. "Hydrogen Bonding Interactions in Amorphous Salicyl Salicylate." Angewandte Chemie 39, no. 20 (October 16, 2000): 3601–4. http://dx.doi.org/10.1002/1521-3773(20001016)39:20<3601::aid-anie3601>3.0.co;2-r.

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40

Tremmel, Peter, and Armin Geyer. "Coupled Hydrogen-Bonding Networks in Polyhydroxylated Peptides." Angewandte Chemie International Edition 43, no. 43 (November 5, 2004): 5789–91. http://dx.doi.org/10.1002/anie.200461099.

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41

Beijer, Felix H., Huub Kooijman, Anthony L. Spek, Rint P. Sijbesma, and E. W. Meijer. "Self-Complementarity Achieved through Quadruple Hydrogen Bonding." Angewandte Chemie International Edition 37, no. 1-2 (February 2, 1998): 75–78. http://dx.doi.org/10.1002/(sici)1521-3773(19980202)37:1/2<75::aid-anie75>3.0.co;2-r.

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42

Caminati, Walther, Laura B. Favero, Paolo G. Favero, Assimo Maris, and Sonia Melandri. "Intermolecular Hydrogen Bonding between Water and Pyrazine." Angewandte Chemie International Edition 37, no. 6 (April 3, 1998): 792–95. http://dx.doi.org/10.1002/(sici)1521-3773(19980403)37:6<792::aid-anie792>3.0.co;2-r.

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43

Amorati, Riccardo, Paola Franchi, and Gian Franco Pedulli. "Intermolecular Hydrogen Bonding Modulates the Hydrogen-Atom-Donating Ability of Hydroquinones." Angewandte Chemie International Edition 46, no. 33 (July 19, 2007): 6336–38. http://dx.doi.org/10.1002/anie.200701957.

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44

Ahsan, Mohd, Chinmai Pindi, and Sanjib Senapati. "Hydrogen bonding catalysis by water in epoxide ring opening reaction." Journal of Molecular Graphics and Modelling 105 (June 2021): 107894. http://dx.doi.org/10.1016/j.jmgm.2021.107894.

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45

Li, Zhi-Hong, Alexey Bulychev, Lakshmi P. Kotra, Irina Massova, and Shahriar Mobashery. "Hydrogen Bonding and Attenuation of the Rate of Enzymic Catalysis." Journal of the American Chemical Society 120, no. 50 (December 1998): 13003–7. http://dx.doi.org/10.1021/ja983063e.

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46

Zu, Liansuo, Jian Wang, Hao Li, Hexin Xie, Wei Jiang, and Wei Wang. "Cascade Michael−Aldol Reactions Promoted by Hydrogen Bonding Mediated Catalysis." Journal of the American Chemical Society 129, no. 5 (February 2007): 1036–37. http://dx.doi.org/10.1021/ja067781+.

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47

Toteva, Maria M., and John P. Richard. "Hydrogen Bonding and Catalysis of Solvolysis of 4-Methoxybenzyl Fluoride." Journal of the American Chemical Society 124, no. 33 (August 2002): 9798–805. http://dx.doi.org/10.1021/ja026849s.

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48

WHITE, ANDREW, SIMON WARD, and CHRISTOPHER WHARTON. "Hydrogen-bonding in chymotrypsin catalysis: Fourier transform infrared spectroscopic analysis." Biochemical Society Transactions 18, no. 4 (August 1, 1990): 660. http://dx.doi.org/10.1042/bst0180660.

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49

Russo, Alessio, and Alessandra Lattanzi. "Hydrogen-Bonding Catalysis: Mild and Highly Chemoselective Oxidation of Sulfides." Advanced Synthesis & Catalysis 351, no. 4 (March 2009): 521–24. http://dx.doi.org/10.1002/adsc.200900020.

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50

Lv, Xinxin, Hehuan Xu, Yanli Yin, Xiaowei Zhao, and Zhiyong Jiang. "Visible Light‐Driven Cooperative DPZ and Chiral Hydrogen‐Bonding Catalysis." Chinese Journal of Chemistry 38, no. 12 (November 25, 2020): 1480–88. http://dx.doi.org/10.1002/cjoc.202000306.

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