scholarly journals Push or Pull for a Better Selectivity? A Study on the Electronic Effects of Substituents of the Pyridine Ring on the Enantiomeric Recognition of Chiral Pyridino-18-Crown-6 Ethers

Symmetry ◽  
2020 ◽  
Vol 12 (11) ◽  
pp. 1795
Author(s):  
Balázs Szemenyei ◽  
Balázs Novotny ◽  
Sarolta Zsolnai ◽  
Zsombor Miskolczy ◽  
László Biczók ◽  
...  
Keyword(s):  
Crown Ether ◽  
Pyridine Ring ◽  
Optically Active ◽  
Primary Amines ◽  
Titration Calorimetry ◽  
Synthetic Route ◽  
Electronic Effects ◽  
Enantiomeric Recognition ◽  
Electronic Effects Of Substituents ◽  
Discriminating Ability

Seven dimethyl-substituted optically active pyridino-18-crown-6 ethers containing various substituents at position 4 of the pyridine ring were studied with regards to the electron-donating and -withdrawing effects of substituents on enantiomeric recognition. In order to compile this set of compounds, we prepared four novel pyridino-18-crown-6 ethers, including an intermediate of a new synthetic route for a formerly reported crown ether. The discriminating ability of these pyridino-crown ethers with C2-symmetry toward the enantiomers of protonated primary amines was examined by isothermal titration calorimetry.

scholarly journals An Electrochemical Evaluation of Novel Ferrocene Derivatives for Glutamate and Liver Biomarker Biosensing

Biosensors ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 254
Author(s):  
Geok Hong Soon ◽  
Mary Deasy ◽  
Eithne Dempsey
Keyword(s):  
Film Studies ◽  
Redox Potentials ◽  
Signal Loss ◽  
Electronic Effects ◽  
Ferrocene Derivatives ◽  
Electroactive Films ◽  
Glutamate Oxidase ◽  
Electronic Effects Of Substituents ◽  
Glutamyl Transpeptidase

Here, we present an evaluation of two new monosubstituted ferrocene (Fc) derivatives, 3-(1H-pyrrol-1-yl)propanamidoferrocene and 1-hydroxy-2-[2-(thiophen-3-yl)-ethylamino]ethylferrocene, as glutamate oxidase mediators, together with their preparation and characterisation. Taking into consideration the influence of the electronic effects of substituents on the redox potentials of the Fc species, two candidates with pyrrole or thiophene moieties were proposed for investigation. Film studies involved potential sweeping in the presence of pyrrole or 3,4-ethylenedioxythiophene monomers resulting in stable electroactive films with % signal loss upon cycling ranging from 1 to 7.82% and surface coverage (Γ) 0.47–1.15 × 10−9 mol/cm2 for films formed under optimal conditions. Construction of a glutamate oxidase modified electrode resulted in second-generation biosensing with the aid of both cyclic voltammetry and hydrodynamic amperometry, resulting in glutamate sensitivity of 0.86–1.28 μA/mM and Km (app) values over the range 3.67–5.01 mM. A follow-up enzyme assay for liver biomarker γ-glutamyl transpeptidase realised unmediated and mediated measurement establishing reaction and incubation time investigations and a realising response over <100 U/L γ-glutamyl transpeptidase with a sensitivity of 5 nA/UL−1.

scholarly journals Enantioselective Transfer Aminoallylation: Synthesis of Optically Active Homoallylic Primary Amines.

ChemInform ◽  
2007 ◽  
Vol 38 (1) ◽  
Author(s):  
Masaharu Sugiura ◽  
Chieko Mori ◽  
Shu Kobayashi
Keyword(s):  
Optically Active ◽  
Primary Amines

scholarly journals New Application of Crown Ether. V. The Effect of Crown Ethers on the Acid–Base Interaction between 2,4,4′,6-Tetranitrodiphenylamine and Primary Amines in Benzene

1981 ◽  
Vol 54 (2) ◽  
pp. 458-461 ◽  
Author(s):  
Fumio Wada ◽  
Yoshiko Wada ◽  
Kiyoshi Kikukawa ◽  
Tsutomu Matsuda
Keyword(s):  
Crown Ether ◽  
Crown Ethers ◽  
Primary Amines ◽  
Acid Base ◽  
Base Interaction ◽  
Acid Base Interaction

Correlation of structural parameters with antituberculotic activity in a group of 2-benzamidobenzothiazoles

1991 ◽  
Vol 56 (12) ◽  
pp. 2978-2985 ◽  
Author(s):  
Karel Waisser ◽  
Jiří Kuneš ◽  
Želmíra Odlerová
Keyword(s):  
Structural Parameters ◽  
Regression Equations ◽  
Electronic Effects ◽  
Active Compounds ◽  
Qsar Analysis ◽  
Active Structures ◽  
Benzoyl Group ◽  
Electronic Effects Of Substituents

Fourteen 2-benzamidobenzothiazole derivatives substituted in the benzoyl group and 2-cinnamamidobenzothiazole have been synthesized. The prediction of active structures by the method by Topliss gives incorrect results but, as shown on the basis of the Hansch QSAR analysis, the 2-(4-dimethylaminobenzamido)benzothiazole synthesized on the basis of the QSAR procedure by Topliss behaves anomalously also in the procedure by Hansch. Regression equations of the Hansch type have been found in which the antituberculotic activity is interpreted by lipophilicity and electronic effects of substituents. When tested in vitro, the most active compounds are comparable with ethionamide.

Transmission of the electronic effects of substituents by the thiophene ring

1974 ◽  
Vol 10 (7) ◽  
pp. 801-805 ◽  
Author(s):  
L. P. Pivovarevich ◽  
L. A. Kutulya ◽  
Yu. N. Surov ◽  
S. V. Tsukerman ◽  
V. F. Lavrushin
Keyword(s):  
Thiophene Ring ◽  
Electronic Effects ◽  
Electronic Effects Of Substituents

ChemInform Abstract: STERIC AND ELECTRONIC EFFECTS OF SUBSTITUENTS AT PHOSPHORUS ON THE COURSE OF THE WITTIG REACTION IN PROTIC SOLVENTS

1974 ◽  
Vol 5 (31) ◽  
Author(s):  
D. W. ALLEN ◽  
P. HEATLEY ◽  
B. G. HUTLEY ◽  
M. T. J. MELLOR
Keyword(s):  
Wittig Reaction ◽  
Electronic Effects ◽  
Protic Solvents ◽  
Electronic Effects Of Substituents

scholarly journals Stereochemical effects during [M-H]− dissociations of epimeric 11-OH-17β-estradiols and distant electronic effects of substituents at C(11) position on gas phase acidity

2009 ◽  
Vol 20 (12) ◽  
pp. 2318-2333 ◽  
Author(s):  
Sandrine Bourgoin-Voillard ◽  
Emilie-Laure Zins ◽  
Françoise Fournier ◽  
Yves Jacquot ◽  
Carlos Afonso ◽  
...  
Keyword(s):  
Gas Phase ◽  
Electronic Effects ◽  
Gas Phase Acidity ◽  
Electronic Effects Of Substituents
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