Article
Chemistry, Multidisciplinary
Alica C. Keuper, Kevin Fengler, Florian Ostler, Tobias Danelzik, Dariusz G. Piekarski, Olga Garcia Mancheno
Summary: A new approach to achieve highly enantioselective halogen-bonding catalysis has been developed by designing fine-tuned halogen-halogen interactions. This strategy utilizes both the electron cloud and sigma-hole site of the substrate's halogen substituent to form a tight chiral complex, enabling controlled induction of high levels of chirality transfer. Remarkable enantioselectivities of up to 95:5 e.r. (90% ee) have been achieved in a model dearomatization reaction using tetrakis-iodotriazole multidentate anion-binding catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zeynab Imani, Venkateswara Rao Mundlapati, Valerie Brenner, Eric Gloaguen, Katia Le Barbu-Debus, Anne Zehnacker-Rentien, Sylvie Robin, David J. Aitken, Michel Mons
Summary: The delta conformation, a local secondary structure in proteins, is stabilized by specific side-chain/backbone N-H interactions in derivatives of a cyclic amino acid with a sulphur atom in the gamma-position. This allows the delta conformation to compete with classical C5 and C7 hydrogen bonded conformers, expanding the range of small-molecule models beyond rigid proline-type compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Chenxiao Qian, Pengfei Li, Jianwei Sun
Summary: A catalytic enantioselective variant of oxidative rearrangement of indoles to access oxindoles has been developed using chiral phosphoric acid catalysis, providing a rapid access to a range of enantioenriched spirooxindoles with high enantioselectivity controlled by dynamic kinetic resolution.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Ming Yu Jin, Qianqian Zhen, Dengmengfei Xiao, Guanyu Tao, Xiangyou Xing, Peiyuan Yu, Chen Xu
Summary: Non-covalent pi interactions play a central role in differentiating enantiomeric substrates in a Sharpless asymmetric dihydroxylation (SAD)-based kinetic resolution.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Physical
Ana Maria Faisca Phillips, Martin H. G. Prechtl, Armando J. L. Pombeiro
Summary: Chiral bifunctional dual H-bond donor catalysts have become essential in organocatalysis, promoting various reactions with high yields and excellent stereoselectivities. Understanding their mechanisms and the origin of stereoselectivity can guide the development of more efficient catalysts for new transformations.
Review
Materials Science, Paper & Wood
Michael C. Jarvis
Summary: It is now understood that the bonding in crystalline cellulose involves hydrogen bonding, dispersion forces, and electrostatic attraction influenced by cellulose conformation. The surface chains of cellulose microfibrils have a different conformation and form different hydrogen bonds depending on their interaction with water, other microfibrils, or non-cellulosic polymers. The specific details of these surface interactions, especially in the presence of other polymers, are still uncertain and require further research.
Article
Chemistry, Organic
Nitika Grover, Keith J. Flanagan, Cristina Trujillo, Christopher J. Kingsbury, Mathias O. Senge
Summary: Bicyclo[1.1.1]pentane (BCP) is extensively studied as a bioisosteric component of drugs. Analysis of BCP derivatives revealed various non-covalent interactions, such as halogen bonding and N-H center dot center dot center dot O contacts, which can be useful for designing BCP analogs of drugs. Computational analysis and structure determinations provide insights into the interaction profiles of BCP derivatives with specific active sites.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bruno Landeros-Rivera, Vojtech Jancik, Rafael Moreno-Esparza, Diego Martinez Otero, Jesus Hernandez-Trujillo
Summary: The study challenges the common assumption about the planar structure of the biphenyl crystal and provides compelling evidence from theoretical computations for its stable molecular arrangement, which is also supported by the experimental results.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Ashanul Haque, Khalaf M. Alenezi, Muhammad S. Khan, Wai-Yeung Wong, Paul R. Raithby
Summary: The design and development of functional materials with practical applications require high standards. Understanding and controlling inter- and intra-molecular interactions offer opportunities for designing new materials. Manipulating the molecular structure can significantly alter these interactions and enhance the properties and functions of the material. Non-covalent interactions (NCIs) have been found to have beneficial effects, indicating that manipulating NCIs can generate functional materials with various physical properties for applications in catalysis, drug delivery, crystal engineering, etc. This review aims to explore the implications of NCIs on molecular packing, optical properties, and applications of functional pi-conjugated materials. Additionally, it attempts to delineate the effects of weak interactions on opto-electronic (O-E) applications.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Biochemistry & Molecular Biology
David B. Hobart, Michael A. G. Berg, Hannah M. Rogers, Joseph S. Merola
Summary: The reaction of palladium(II) acetate with acyclic amino acids in acetone/water produces square planar bis-chelated palladium amino acid complexes with interesting non-covalent interactions. The molecular structures of the products, including the incorporation of water molecules and N-H···O and/or O···(HOH)···O hydrogen bonding interactions, were discussed in terms of the extended lattice structures exhibited by the complexes. Multiple spectroscopic techniques were used for analysis, with some cases allowing for single crystal X-ray diffraction to obtain the molecular structure.
Article
Chemistry, Multidisciplinary
Nobuya Tsuji, Pavel Sidorov, Chendan Zhu, Yuuya Nagata, Timur Gimadiev, Alexandre Varnek, Benjamin List
Summary: Catalyst optimization processes often rely on qualitative assumptions of chemists based on screening data, while machine learning models using molecular properties or calculated 3D structures are time-consuming and costly. This study proposes a machine learning model based on fragment descriptors, which are fine-tuned for asymmetric catalysis and result in robust and efficient virtual screening. Through theoretical design and experimental validation, new catalysts with higher selectivities in a challenging synthesis were developed using only moderately selective training data.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Haia Kharraz, Hadi Hachem, Yann Le Gal, Thierry Roisnel, Olivier Jeannin, Frederic Barriere, Thierry Guizouarn, Dominique Lorcy
Summary: Tetrathiafulvalenes (TTFs) were functionalized with groups that enhance non-covalent intermolecular interactions. The study involved designing appropriate precursors and assessing the electronic effect of the substituents on the overall donating ability of the TTFs. Charge transfer salts were prepared and their crystal structures were analyzed to understand the stacking mode and non-covalent interactions in the solid state.
Article
Chemistry, Organic
Yanli Yin, Yifan Fan, Xiaowei Zhao, Guobi Chai, Zhiyong Jiang
Summary: The first catalytic asymmetric Mannich reaction of 5-substituted oxazolidine-2,4-diones is reported, showing high enantio- and diastereoselectivities. By utilizing different catalysts, it is possible to switch the diastereoselectivity and achieve good to excellent enantioselectivities in the synthesis of valuable oxazolidine-2,4-ones.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiangpei Chai, Xinheng Hu, Xiaowei Zhao, Yanli Yin, Shanshan Cao, Zhiyong Jiang
Summary: This research reports a radical-based manifold that achieves highly enantioselective transformations of N-arylglycines. The dual catalytic system involving a chiral phosphoric acid and a photoredox sensitizer offers a new approach for the synthesis of valuable organic compounds with satisfactory results and high enantiocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
V. S. Jeba Reeda, P. Divya, R. Suja, A. Rathika, V. Bena Jothy
Summary: Piperazine Succinate (PZSN) was synthesized and analyzed using various spectroscopic techniques. The molecule's geometry was optimized and it was found that the elongation of the C21-H25 bond length in PZSN can be attributed to the intermolecular hydrogen bonding interaction. Natural bond orbital analysis indicated a charge transfer between LP(1) N2 and sigma*(C21-H25), providing evidence for the presence of intermolecular hydrogen bonding interactions. The IR spectrum revealed a strong band assigned to N2-H16 stretching mode, supporting the formation of a hydrogen bond between succinate C=O and piperazine NH group.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
