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Relevant bibliographies by topics / Hydrogen-Bonding Catalysis

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Academic literature on the topic 'Hydrogen-Bonding Catalysis'

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Published: 6 September 2023

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Journal articles on the topic "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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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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Hydrogen-Bonding Catalysis"

1

Taylor, Russell Alan. "Hydrogen bonding effects in homogeneous catalysis." Thesis, Imperial College London, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.500138.

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Tossell, Katie Jayne. "Catalysis of phosphate ester hydrolysis through hydrogen bonding." Thesis, University of Sheffield, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.578696.

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This thesis describes the investigation of the effect of hydrogen bonding on the rate of phosphoryl transfer in the reaction of diethyl 8-dimethylamino-I-naphthyl phosphate 3 with a nucleophile. The study of the hydrolysis of triester 3 is in the literature; triester 3 is catalysed by the dimethylammonium general acid, with a rate acceleration of almost 106 in comparison to the hydrolysis of diethyl I-naphthyl phosphate. 58 To ascertain whether the reactivity of triester 3 is specific to this system, the methylation of the amine in triester 3 was altered. Triesters diethyl 8- amino-I-naphthyl phosphate 6 and diethyl 8-methyIamino-l-naphthyl phosphate 7 were synthesised and their reaction with water and hydroxylamine was studied. It is concluded that the effect of methylation of the amine on the rate of P-O cleavage in triester 3 is insignificant, and that the hydrogen bond donor ability of the amino proton donor is not an important factor in increasing the rate of P-O cleavage; the energy of triesters 6H+, 7H+ and 3H+ are very similar. The hydrolysis of 8-dimethylamino-l-naphthyl phosphate 5m is also known to exhibit general acid catalysis by the dimethylammonium group." To ascertain whether the effect of methylation of the amine on the rate of p-o cleavage in monoester 5mis also insignificant, the hydrolysis of 8- rnethylamino-I-naphthyl phosphate 27m was studied. It is concluded that methylation of the amino general acid in triester 6H+ and monoester 5m has no significant effect on the rate of phosphoryl transfer, regardless of the different transition states that are formed. By studying the hydrolysis of monoester 36d it is concluded that the reactivity of monoester 5m is also dependent on the proton donor ability of the amino group. The elimination of various functionalised 8-amino-I-tetralone-3-sulfonic acids with hydroxide has been studied. There is a clear difference between the rates of elimination of the tetralones upon varying the proton donor ability of the amino group. No apparent trend relating the rate of elimination to the proton donor ability of the hydrogen bond donor, or to the pKa of the conjugate acid of the tetralones is observed.

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Jones, Christopher Raymond. "Hydrogen bonding : from conformational control to asymmetric catalysis." Thesis, University of Cambridge, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.611778.

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Snowden, Timothy Scott. "Hydrogen bond involvement in carbon acid pKa[subscript] shifts and intramolecular general catalysis /." Full text (PDF) from UMI/Dissertation Abstracts International, 2001. http://wwwlib.umi.com/cr/utexas/fullcit?p3008444.

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Brown, Christopher John. "Efficient intramolecular general acid catalysis." Thesis, University of Cambridge, 1995. https://www.repository.cam.ac.uk/handle/1810/272266.

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White, M. S. "Reactions and laser activation of carbon acids in hydrogen bonding environments." Thesis, University of York, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.372762.

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Pan, Yongping. "Characterization of Low Barrier Hydrogen Bonds in Enzyme Catalysis: an Ab Initio and DFT Investigation." Thesis, University of North Texas, 1999. https://digital.library.unt.edu/ark:/67531/metadc278586/.

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Hartree-Fock, Moller-Plesset, and density functional theory calculations have been carried out using 6-31+G(d), 6-31+G(d,p) and 6-31++G(d,p) basis sets to study the properties of low-barrier or short-strong hydrogen bonds (SSHB) and their potential role in enzyme-catalyzed reactions that involve proton abstraction from a weak carbon-acid by a weak base. Formic acid/formate anion, enol/enolate and other complexes have been chosen to simulate a SSHB system. These complexes have been calculated to form very short, very short hydrogen bonds with a very low barrier for proton transfer from the donor to the acceptor. Two important environmental factors including small amount of solvent molecules that could possibly exist at the active site of an enzyme and the polarity around the active site were simulated to study their energetic and geometrical influences to a SSHB. It was found that microsolvation that improves the matching of pK as of the hydrogen bond donor and acceptor involved in the SSHB will always increase the interaction of the hydrogen bond; microsolvation that disrupts the matching of pKas, on the other hand, will lead to a weaker SSHB. Polarity surrounding the SSHB, simulated by SCRF-SCIPCM model, can significantly reduce the strength and stability of a SSHB. The residual strength of a SSHB is about 10--11 kcal/mol that is still significantly stable compared with a traditional weak hydrogen bond that is only about 3--5 kcal/mol in any cases. These results indicate that SSHB can exist under polar environment. Possible reaction intermediates and transition states for the reaction catalyzed by ketosteroid isomerase were simulated to study the stabilizing effect of a SSHB on intermediates and transition states. It was found that at least one SSHB is formed in each of the simulated intermediate-catalyst complexes, strongly supporting the LBHB mechanism proposed by Cleland and Kreevoy. Computational results on the activation energy for catalyzed and uncatalyzed model reactions shows that strong hydrogen bonding between catalyst and the substrate at the transition state can significantly reduce the activation energy. This implies that LBHBs are possibly playing a crucial role in enzyme catalysis by supplying significant stabilizing energy to the reaction transition state.

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Brown, Adam Ross. "I. Engaging Cationic Intermediates in Asymmetric Catalysis: Enantioselective Reactions of Carbenium Ions and N,N-Dialkyliminium Ions II. Enantioselective Catalysis of the Cope-Type Hydroamination by H-Bond Donors." Thesis, Harvard University, 2013. http://dissertations.umi.com/gsas.harvard:11009.

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The research described here explores the ability of dual H-bond donor catalysts to induce asymmetry in a variety of synthetically useful transformations that proceed via diverse reactive intermediates. In Chapters 1-3, we investigate ureas and thioureas as anion-binding catalysts for asymmetric reactions that proceeed via cationic intermediates with little precedent as electrophiles in asymmetric catalysis. Chapter 4 details our application of H-bond donor catalysis to the Cope-type hydroamination. Chapter 1 describes the development of an asymmetric aldehyde alkylation catalyzed by a bifunctional primary aminothiourea. A variety of 2-aryl propionaldehydes are alkylated with benzhydryl bromides in moderate to good yields and good enantioselectivities. Catalyst structure-activity relationship studies of the alkylation pointed towards electrophile activation by the dual H-bond donor moiety. Experiments aimed at gaining a better understanding of the electophile activation mode and characterizing the activated electrophilic intermediate in the alkylation reaction are described in Chapter 2. The development of an enantioselective cyanide addition to N,N-dialkyliminium intermediates is the subject of Chapter 3. A variety of strategies for accessing N,N- dialkyliminium ions are established, and chiral thioureas are shown to promote the addition of cyanide to such intermediates with moderate enantioselectivities. Chapter 4 details our discovery that thioureas bearing polarizable and conformationally constrained aromatic groups catalyze highly enantioselective Cope-type hydroaminations. This powerful transformation provides a variety of chiral pyrrolidine products under mild reaction conditions.
Chemistry and Chemical Biology

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9

McGrath, Jacqueline. "Advances in Supramolecular Catalysis: Studies of Bifurcated Hamilton Receptors." Thesis, University of Oregon, 2016. http://hdl.handle.net/1794/19691.

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Bidentate ligands are a commonly used class of ligands in catalysis that generate highly-active and selective catalysts. Such bidentate ligands, however, often suffer from synthetic challenges, which can be alleviated by the use of simpler monodentate ligands that assemble through non-covalent interactions to mimic the structure of bidentate ligands at the metal center. To produce a strongly assembled catalyst complex, the Hamilton receptor motif was utilized. Hamilton receptors form six hydrogen bonds with complementary guests and have binding affinities for barbiturates of up to 104 M-1 in CDCl3. Complete bifurcation of the Hamilton scaffold produces a modular ligand structure that allows for modification of either end of the supramolecular ligand structure. Similarly, the barbiturate guest can be synthetically altered creating both chiral guests and guests with differing amounts of steric bulk. Both experimental titration data and density functional theory calculations show that steric bulk discourages binding of the guest while a pre-organized host encourages guest inclusion. Electronic effects on the bifurcated Hamilton system were studied by varying the electron donating or withdrawing ability of the benzamide moiety on the host molecule. Electron withdrawing moieties produce more acidic amide hydrogens on the host which are able to participate in stronger hydrogen bonds with the guest resulting in a stronger host-guest complex. The effects of substitutions on the barbiturate guest were examined as well, and increased steric bulk on the guest resulted in decreased affinities with the host. The bifurcated Hamilton receptor ligands were examined in the palladium-catalyzed Heck reaction of iodobenzene with butyl acrylate. Pd2(OAc)4 was used as a control and all reaction yields with the diphenylphosphine ligand-stabilized Pd were greater than or equal to those obtained with Pd2(OAc)4 alone. The reaction rates did not correlate with the determined binding constants, suggesting that phosphine substitution on the guest plays a larger role than affinity of the complex for the guest. Reaction temperatures were varied, and at lower temperatures the yields increased implying that the strength of the hydrogen bonds between the metal complex and the guest does play a secondary role in the catalysis. This dissertation includes previously published co-authored material.

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10

Goudreault, Alexandre. "Roles for Nucleophiles and Hydrogen-Bonding Agents in the Decomposition of Phosphine-Free Ruthenium Metathesis Catalysts." Thesis, Université d'Ottawa / University of Ottawa, 2020. http://hdl.handle.net/10393/40042.

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With its unrivaled versatility and atom economy, olefin metathesis is arguably the most powerful catalyst methodology now known for the construction of carbon-carbon bonds. When compared to palladium-catalyzed cross-coupling methodologies, however, catalyst productivity lags far behind, even for the “robust” ruthenium metathesis catalysts. Unexpected limitations to the robustness of these catalysts were first widely publicized by reports describing the implementation of metathesis in pharmaceutical manufacturing. Recurring discussion centered on low catalyst productivity resulting from decomposition of the Ru catalysts by impurities, including ppm-level contaminants in the technical-grade solvent. Over the past 7 years, a series of mechanistic studies from the Fogg group has uncovered the pathways by which common contaminants (or indeed reagents) trigger catalyst decomposition. Two principal pathways were identified: abstraction of the alkylidene or methylidene ligand by nucleophiles, and deprotonation of the metallacyclobutane intermediate by Bronsted base. Emerging applications, however, notably in chemical biology, highlight new challenges to catalyst productivity. The first part of this thesis emphasizes the need for informed mechanistic insight as a guide to catalyst redesign. The widespread observation of a cyclometallated N-heterocyclic carbene (NHC) motif in crystal structures of catalyst decomposition products led to the presumption that activation of a C-H bond in the NHC ligand initiates catalyst decomposition. Reducing NHC bulk has therefore been proposed as critical to catalyst redesign. In experiments designed to probe the viability of this solution, the small NHC ligand IMe4 (tetramethylimidazol-2-ylidene) was added to the resting-state methylidene complexes formed in metathesis by the first- and second-generation Grubbs catalysts (RuCl2(PCy3)2(=CH2) GIm or RuCl2(H2IMes)(PCy3)(=CH2) GIIm, respectively). The intended product, a resting-state methylidene species bearing a truncated NHC, was not formed, owing to immediate loss of the methylidene ligand. Methylidene loss is now shown to result from nucleophilic attack by the NHC – a small, highly potent nucleophile – on the methylidene. Density functional calculations indicate that IMe4 abstracts the methylidene, generating the N-heterocyclic olefin H2C=IMe4. The latter is an even more potent nucleophile, which attacks a second methylidene, resulting in liberation of [EtIMe4]Cl. These findings report indirectly on the original question concerning the impact of ligand truncation. The ease with which a small, potent nucleophile can abstract the key methylidene ligand from GIm and GIIm underscores the importance of increasing steric protection at the [Ru]=CH2 site. This chemistry also suggests intriguing possibilities for efficient, selective, controlled methylidene abstraction to terminate metathesis activity while leaving the “RuCl2(H2IMes)(PCy3)” core intact. This could prove an enabling strategy for tandem catalysis applications in which metathesis is the first step. The second part of this thesis, inspired by the potential of olefin metathesis in chemical biology, focuses on the impact of hydroxide ion and water on the productivity of phosphine-free metathesis catalysts. In reactions with the important second-generation Hoveyda catalyst HII, hydroxide anion is found to engage in salt metathesis with the chloride ligands, rather than nucleophilic attack. The resulting Ru-hydroxide complex is unreactive toward any olefins larger than ethylene, while ethylene itself causes rapid decomposition. Proposed as the decomposition pathway is bimolecular coupling promoted by the strong H-bonding character of the hydroxide ligands. Lastly, the impact of the water on Ru-catalyzed olefin metathesis is examined. In a survey of normally facile metathesis reactions using state-of-the-art catalysts, even trace water (0.1% v/v) is found to be highly detrimental. The impact of water is shown to be greater at room temperature than previously established at 60 °C. Preliminary evidence strongly suggests that the mechanism by which water induces decomposition is temperature-dependent. Thus, at high temperature, decomposition of the metallacyclobutane intermediate appears to dominate, but this pathway is ruled out at ambient temperatures. Instead, water is proposed to promote bimolecular decomposition. Polyphenol resin, which can sequester water by H-bonding, is shown to offer an interim solution to the presence of trace water in organic media. These findings suggest that major avenues of investigation aimed at reducing intrinsic catalyst decomposition may likewise be relevant to the development of water-tolerant catalysts.

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Books on the topic "Hydrogen-Bonding Catalysis"

1

White, Andrew Jack. Hydrogen bonding and catalysis in acyl-chymotrypsins: A study by infrared spectroscopy. Birmingham: University of Birmingham, 1992.

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Inokuma, Tsubasa. Development of Novel Hydrogen-Bond Donor Catalysts. Springer London, Limited, 2013.

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Inokuma, Tsubasa. Development of Novel Hydrogen-Bond Donor Catalysts. Springer, 2013.

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Inokuma, Tsubasa. Development of Novel Hydrogen-Bond Donor Catalysts. Springer, 2015.

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Development Of Novel Hydrogenbond Donor Catalysts. Springer Verlag, Japan, 2012.

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Book chapters on the topic "Hydrogen-Bonding Catalysis"

1

Arimitsu, Satoru, and Masahiro Higashi. "CHAPTER 2. Importance of C–H Hydrogen Bonding in Asymmetric Catalysis." In Catalysis Series, 26–65. Cambridge: Royal Society of Chemistry, 2019. http://dx.doi.org/10.1039/9781788016490-00026.

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Raposo, C., M. Crego, M. Almaraz, M. L. Mussons, M. Martín, V. Weinrich, M. C. Caballero, and J. R. Morán. "A Study of the Catalytic Properties of Some Hydrogen Bonding Receptors." In Molecular Design and Bioorganic Catalysis, 87–110. Dordrecht: Springer Netherlands, 1996. http://dx.doi.org/10.1007/978-94-009-1679-1_6.

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Zhai, Y., S. Wang, and Steven S. C. Chuang. "CHAPTER 23. The Nature of Hydrogen Bonding in Adsorbed CO2 and H2O on Solid Amines in CO2 Capture." In Catalysis Series, 503–26. Cambridge: Royal Society of Chemistry, 2019. http://dx.doi.org/10.1039/9781788016490-00503.

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Mbofana, Curren T., and Scott J. Miller. "Bifunctional Catalysis with Lewis Base and X-H Sites That Facilitate Proton Transfer or Hydrogen Bonding (n?→?π*)." In Lewis Base Catalysis in Organic Synthesis, 1259–88. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2016. http://dx.doi.org/10.1002/9783527675142.ch26.

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Ross, James, and Jianliang Xiao. "The Importance of Hydrogen Bonding to Catalysis in Ionic Liquids: Inhibition of Allylic Substitution and Isomerization by [bmim][BF4]." In ACS Symposium Series, 314–22. Washington, DC: American Chemical Society, 2003. http://dx.doi.org/10.1021/bk-2003-0856.ch026.

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Türkmen, Yunus Emre. "Alcohols and Phenols as Hydrogen Bonding Catalysts." In Nonnitrogenous Organocatalysis, 13–37. Boca Raton, Florida : CRC Press, [2018] | Series: Organocatalysis series: CRC Press, 2017. http://dx.doi.org/10.1201/9781315371238-2.

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Milan, M., and V. Nedeljko. "Electrocatalytic and Hydridic Theory for Hydrogen Electrode Reactions and Prediction of Synergetic Catalysts in the Light of Fermi Dynamics and Structural Bonding Factors." In Hydrogen Power: Theoretical and Engineering Solutions, 103–18. Dordrecht: Springer Netherlands, 1998. http://dx.doi.org/10.1007/978-94-015-9054-9_12.

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"Hydrogen-Bonding Catalysts: (Thio)urea Catalysis." In Asymmetric Organocatalysis 2, edited by Maruoka. Stuttgart: Georg Thieme Verlag, 2012. http://dx.doi.org/10.1055/sos-sd-205-00205.

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Oestreich, M. "Ruthenium(II) Catalysis Assisted by Hydrogen Bonding." In Aldehydes, 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-025-00155.

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Shan, Shu-ou, and Daniel Herschlag. "[11] Hydrogen bonding in enzymatic catalysis: Analysis of energetic contributions." In Methods in Enzymology, 246–76. Elsevier, 1999. http://dx.doi.org/10.1016/s0076-6879(99)08013-1.

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