Improving phase-transfer catalysis by enhancing non-covalent interactions

2020 ◽  
Vol 22 (37) ◽  
pp. 21015-21021
Author(s):  
Iñigo Iribarren ◽  
Cristina Trujillo
Keyword(s):  
Hydrogen Bond ◽  
Phase Transfer Catalysis ◽  
Theoretical Study ◽  
Phase Transfer ◽  
Intermolecular Hydrogen Bond ◽  
Ion Pairing ◽  
Non Covalent Interactions ◽  
Covalent Interactions

A theoretical study of the interactions established between an alkaloid quinine-derived PTC and different anions of interest was performed. Ion pairing competes with an intermolecular hydrogen bond between the PT counteranion and potential HB donors.

scholarly journals Improving Phase-Transfer Catalysis by Enhancing Non-Covalent Interactions

2020 ◽  
Author(s):  
Iñigo Iribarren ◽  
Cristina Trujillo
Keyword(s):  
Asymmetric Catalysis ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Intermolecular Hydrogen Bond ◽  
Pair Interaction ◽  
Unsaturated Ketone ◽  
Asymmetric Transformations ◽  
The Past ◽  
Non Covalent Interactions ◽  
Covalent Interactions

<p>A wide variety of asymmetric transformations catalysed by chiral catalysts have been developed for the synthesis of valuable organic compounds in the past several decades. Within asymmetric catalysis field, phase-transfer catalysis has been recognized as a powerful method for establishing useful procedures for organic synthesis. In the present study intermolecular interactions between a well-known alkaloid quinine-derived phase transfer catalyst and four different anions were characterised, analysing the competition between the pure ion-pair interaction and the intermolecular hydrogen bond established upon complexation. Finally, the energy profile corresponding to the enantioselective conjugate cyanation of a a,b-unsaturated ketone, under the presence of two different catalysts were performed.</p>

scholarly journals Improving Phase-Transfer Catalysis by Enhancing Non-Covalent Interactions

2020 ◽  
Author(s):  
Iñigo Iribarren ◽  
Cristina Trujillo
Keyword(s):  
Asymmetric Catalysis ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Intermolecular Hydrogen Bond ◽  
Pair Interaction ◽  
Unsaturated Ketone ◽  
Asymmetric Transformations ◽  
The Past ◽  
Non Covalent Interactions ◽  
Covalent Interactions

<p>A wide variety of asymmetric transformations catalysed by chiral catalysts have been developed for the synthesis of valuable organic compounds in the past several decades. Within asymmetric catalysis field, phase-transfer catalysis has been recognized as a powerful method for establishing useful procedures for organic synthesis. In the present study intermolecular interactions between a well-known alkaloid quinine-derived phase transfer catalyst and four different anions were characterised, analysing the competition between the pure ion-pair interaction and the intermolecular hydrogen bond established upon complexation. Finally, the energy profile corresponding to the enantioselective conjugate cyanation of a a,b-unsaturated ketone, under the presence of two different catalysts were performed.</p>

scholarly journals Probing the Effect of Halogen Substituents (Br, Cl, and F) on the Non-covalent Interactions in 1-(Adamantan-1-yl)-3-arylthiourea Derivatives: A Theoretical Study

ACS Omega ◽  
2021 ◽  
Vol 6 (7) ◽  
pp. 4816-4830
Author(s):  
Lamya H. Al-Wahaibi ◽  
Divya Sri Grandhi ◽  
Samar S. Tawfik ◽  
Nora H. Al-Shaalan ◽  
Mohammed A. Elmorsy ◽  
...  
Keyword(s):  
Theoretical Study ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Halide ion-driven self-assembly of Zn(ii) compounds derived from an asymmetrical hydrazone building block: a combined experimental and theoretical study

2016 ◽  
Vol 40 (12) ◽  
pp. 10116-10126 ◽  
Author(s):  
Ghodrat Mahmoudi ◽  
Farhad Akbari Afkhami ◽  
Himanshu Sekhar Jena ◽  
Parisa Nematollahi ◽  
Mehdi D. Esrafili ◽  
...  
Keyword(s):  
Self Assembly ◽  
Building Block ◽  
Theoretical Study ◽  
Counter Ion ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Self-assembly of Zn(ii) compounds is influenced by a counter ion and non-covalent interactions.

scholarly journals New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

2016 ◽  
Vol 12 ◽  
pp. 2834-2848 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Recent Progress ◽  
Halogen Bonds ◽  
Hydrogen Bond Donor ◽  
New Approaches ◽  
Substrate Activation ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Hydrogen Bond Donors

Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

scholarly journals Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

RSC Advances ◽  
2016 ◽  
Vol 6 (38) ◽  
pp. 31861-31870 ◽  
Author(s):  
Amedeo Capobianco ◽  
Antonia Di Mola ◽  
Valentina Intintoli ◽  
Antonio Massa ◽  
Vito Capaccio ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Phase Transfer Catalysis ◽  
Theoretical Study ◽  
Phase Transfer ◽  
Chiral Phase

The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of amines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC).

scholarly journals Non-covalent interactions of uranyl complexes: a theoretical study

2018 ◽  
Vol 20 (22) ◽  
pp. 15380-15388 ◽  
Author(s):  
James A. Platts ◽  
Robert J. Baker
Keyword(s):  
Ab Initio ◽  
Theoretical Study ◽  
Halogen Bonding ◽  
Uranyl Complexes ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Ab initio and DFT data quantify the ability of model uranyl complexes to engage in hydrogen- and halogen-bonding, quantifying the weakness of U–Oyl as an acceptor but the strength of equatorial OH2 as a donor.

scholarly journals Supramolecular interactions between catalytic species allow rational control over reaction kinetics

2019 ◽  
Vol 10 (39) ◽  
pp. 9115-9124 ◽  
Author(s):  
Abraham J. P. Teunissen ◽  
Tim F. E. Paffen ◽  
Ivo A. W. Filot ◽  
Menno D. Lanting ◽  
Roy J. C. van der Haas ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Reaction Kinetics ◽  
Phase Transfer ◽  
Supramolecular Interactions ◽  
Two Phase ◽  
Phase Transfer Catalysts ◽  
System P ◽  
Non Covalent Interactions ◽  
Rational Control ◽  
Covalent Interactions

The non-covalent interactions between two phase-transfer catalysts allow tuning of reaction kinetics from bimolecular, to pseudo 0th order, to sigmoidal. Kinetic models and DFT calculations are used to obtain detailed insight in the system.

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