Modified Kagan's amide: synthesis and application as a chiral solvating agent for hydrogen-bonding based chiral discrimination in NMR

RSC Advances ◽  
2015 ◽  
Vol 5 (57) ◽  
pp. 45943-45955 ◽  
Author(s):  
Nilesh Jain ◽  
Ravi B. Patel ◽  
Ashutosh V. Bedekar
Keyword(s):  
Hydrogen Bonding ◽  
Optically Active ◽  
Chiral Discrimination ◽  
Amide Synthesis ◽  
Chiral Solvating Agent

A modified Kagan's amide, N-((S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl)-3,5-dinitrobenzamide has been designed, synthesized and screened as a Chiral Solvating Agent for discrimination of optically active substrates.

Dynamic optical activity induction in the N-alkyl-N′-trityl ureas and thioureas

2019 ◽  
Vol 17 (33) ◽  
pp. 7782-7793 ◽  
Author(s):  
Natalia Prusinowska ◽  
Agnieszka Czapik ◽  
Martika Wojciechowska ◽  
Marcin Kwit
Keyword(s):  
Hydrogen Bonding ◽  
Optical Activity ◽  
Optically Active ◽  
Thiourea Derivatives ◽  
Hydrogen Bonding Network ◽  
Activity Induction

Stereodynamic trityl group, utilized as a reporter of chirality, hampers hydrogen bonding network in optically active urea and thiourea derivatives.

Synthesis of optically active sulphilimines via chiral discrimination

1981 ◽  
pp. 3118 ◽  
Author(s):  
Rita Annunziata ◽  
Mauro Cinquini ◽  
Stefano Colonna ◽  
Franco Cozzi
Keyword(s):  
Optically Active ◽  
Chiral Discrimination

Application of optically active aminonaphthols as NMR solvating agents for chiral discrimination of mandelic acid

2014 ◽  
Vol 25 (9) ◽  
pp. 767-774 ◽  
Author(s):  
Anju R. Chaudhary ◽  
Priyanka Yadav ◽  
Ashutosh V. Bedekar
Keyword(s):  
Mandelic Acid ◽  
Optically Active ◽  
Chiral Discrimination

Variations on a Cage Theme: Some Complexes of Bicyclic Polyamines as Supramolecular Synthons

2009 ◽  
Vol 62 (10) ◽  
pp. 1246 ◽  
Author(s):  
Ian J. Clark ◽  
Alessandra Crispini ◽  
Paul S. Donnelly ◽  
Lutz M. Engelhardt ◽  
Jack M. Harrowfield ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Aromatic Ring ◽  
Oxidation State ◽  
Metal Ion ◽  
Intermolecular Forces ◽  
Optically Active ◽  
Alphabetical Order ◽  
Supramolecular Synthons ◽  
Π Stacking ◽  
Parallel Arrays

Dedication: One of Alan Sargeson’s great abilities was to seek out knowledge on topics of which he was not the master from those people with the expertise. This led occasionally to publications with a ‘cricket team’ of authors but with a rich brew of information, often international. Alan also insisted that all authors were equal since, without any one, the paper would not be what it was. Hence, he endeavoured to pursue the policy, difficult to maintain over a period where an obsession with absurdities such as the order of authors and point-scoring based on meaningless publication indices became so important in the maintenance of research, of listing authors simply in alphabetical order. In describing work begun while he was still with us, we have attempted to adhere to his principles. Analysis of a body of crystallographic information concerning metal(ii) and metal(iii) complexes of macrobicyclic hexamine ligands and some of their derivatives provides evidence for the action of a variety of intermolecular forces within the lattices. Hydrogen bonding is universal and its forms depend strongly upon the oxidation state and the particular nature of the metal ion bound to the macrobicycle. The introduction of both aliphatic and aromatic substituents leads to lattices in which these substituents associate, although, in the case of aromatic substituents, this is not necessarily a consequence of ‘π-stacking’, despite the fact that the aromatic ring planes form parallel arrays. At least in the case of CoIII, stable enantiomers of the complexes can be obtained, and in {Δ-(+)589-[Co{(NH3)(CH3)sar}]}2Cl2(C6(CO2)6)·26H2O (sar = 3,6,10,13,16,19-hexa-azabicyclo[6.6.6]icosane), the benzene hexacarboxylate anion adopts a chiral conformation in the presence of the optically active cation.

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