Model for electrochemical parameters for 4-(benzylsulfanyl)pyridines calculated from the molecular structure

Karel Nesměrák, Andrey A. Toropov, Alla P. Toropova

Research output: Contribution to journalArticle

Abstract

As the half-wave potential is an important electrochemical property used for the characterization of organic compounds, this study is aimed to build up a QSPR model of half-wave oxidation potential of 4-(benzylsulfanyl)pyridines. Firstly, mechanism of electrochemical oxidation of 4-(benzylsulfanyl)pyridines as a model of their possible metabolic degradation was elucidated by preparative electrolysis and GC-MS analysis of oxidative products. Secondly, the QSPR of a half-wave potential of 4-(benzylsulfanyl)pyridines has been performed by two computational approaches: (i) optimal descriptors calculated with Simplified Molecular Input Line Entry System (SMILES), and (ii) classical Hammett constants. Both models have been proved to be statistically significant, and the statistical qualities of both computational approaches are comparable. The mechanistic interpretations of both approaches have been given, and their results gave complementary views on effect of structure of molecular fragments of substituents on the half-wave potential of examined compounds.

Original languageEnglish
Pages (from-to)24-29
Number of pages6
JournalJournal of Electroanalytical Chemistry
Volume766
DOIs
Publication statusPublished - Apr 1 2016

Fingerprint

Pyridines
Pyridine
Molecular structure
Electrochemical oxidation
Electrochemical properties
Electrolysis
Organic compounds
Degradation
Oxidation

Keywords

  • 4-(Benzylsulfanyl) pyridine
  • Electrooxidation
  • Half-wave potential
  • Hammett constant
  • Monte Carlo method

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Analytical Chemistry
  • Electrochemistry

Cite this

Model for electrochemical parameters for 4-(benzylsulfanyl)pyridines calculated from the molecular structure. / Nesměrák, Karel; Toropov, Andrey A.; Toropova, Alla P.

In: Journal of Electroanalytical Chemistry, Vol. 766, 01.04.2016, p. 24-29.

Research output: Contribution to journalArticle

@article{7bfaeb83f5d1415998552a5989c6aeae,
title = "Model for electrochemical parameters for 4-(benzylsulfanyl)pyridines calculated from the molecular structure",
abstract = "As the half-wave potential is an important electrochemical property used for the characterization of organic compounds, this study is aimed to build up a QSPR model of half-wave oxidation potential of 4-(benzylsulfanyl)pyridines. Firstly, mechanism of electrochemical oxidation of 4-(benzylsulfanyl)pyridines as a model of their possible metabolic degradation was elucidated by preparative electrolysis and GC-MS analysis of oxidative products. Secondly, the QSPR of a half-wave potential of 4-(benzylsulfanyl)pyridines has been performed by two computational approaches: (i) optimal descriptors calculated with Simplified Molecular Input Line Entry System (SMILES), and (ii) classical Hammett constants. Both models have been proved to be statistically significant, and the statistical qualities of both computational approaches are comparable. The mechanistic interpretations of both approaches have been given, and their results gave complementary views on effect of structure of molecular fragments of substituents on the half-wave potential of examined compounds.",
keywords = "4-(Benzylsulfanyl) pyridine, Electrooxidation, Half-wave potential, Hammett constant, Monte Carlo method",
author = "Karel Nesměr{\'a}k and Toropov, {Andrey A.} and Toropova, {Alla P.}",
year = "2016",
month = "4",
day = "1",
doi = "10.1016/j.jelechem.2016.01.032",
language = "English",
volume = "766",
pages = "24--29",
journal = "Journal of Electroanalytical Chemistry",
issn = "0022-0728",
publisher = "Elsevier Sequoia",

}

TY - JOUR

T1 - Model for electrochemical parameters for 4-(benzylsulfanyl)pyridines calculated from the molecular structure

AU - Nesměrák, Karel

AU - Toropov, Andrey A.

AU - Toropova, Alla P.

PY - 2016/4/1

Y1 - 2016/4/1

N2 - As the half-wave potential is an important electrochemical property used for the characterization of organic compounds, this study is aimed to build up a QSPR model of half-wave oxidation potential of 4-(benzylsulfanyl)pyridines. Firstly, mechanism of electrochemical oxidation of 4-(benzylsulfanyl)pyridines as a model of their possible metabolic degradation was elucidated by preparative electrolysis and GC-MS analysis of oxidative products. Secondly, the QSPR of a half-wave potential of 4-(benzylsulfanyl)pyridines has been performed by two computational approaches: (i) optimal descriptors calculated with Simplified Molecular Input Line Entry System (SMILES), and (ii) classical Hammett constants. Both models have been proved to be statistically significant, and the statistical qualities of both computational approaches are comparable. The mechanistic interpretations of both approaches have been given, and their results gave complementary views on effect of structure of molecular fragments of substituents on the half-wave potential of examined compounds.

AB - As the half-wave potential is an important electrochemical property used for the characterization of organic compounds, this study is aimed to build up a QSPR model of half-wave oxidation potential of 4-(benzylsulfanyl)pyridines. Firstly, mechanism of electrochemical oxidation of 4-(benzylsulfanyl)pyridines as a model of their possible metabolic degradation was elucidated by preparative electrolysis and GC-MS analysis of oxidative products. Secondly, the QSPR of a half-wave potential of 4-(benzylsulfanyl)pyridines has been performed by two computational approaches: (i) optimal descriptors calculated with Simplified Molecular Input Line Entry System (SMILES), and (ii) classical Hammett constants. Both models have been proved to be statistically significant, and the statistical qualities of both computational approaches are comparable. The mechanistic interpretations of both approaches have been given, and their results gave complementary views on effect of structure of molecular fragments of substituents on the half-wave potential of examined compounds.

KW - 4-(Benzylsulfanyl) pyridine

KW - Electrooxidation

KW - Half-wave potential

KW - Hammett constant

KW - Monte Carlo method

UR - http://www.scopus.com/inward/record.url?scp=84957599879&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84957599879&partnerID=8YFLogxK

U2 - 10.1016/j.jelechem.2016.01.032

DO - 10.1016/j.jelechem.2016.01.032

M3 - Article

AN - SCOPUS:84957599879

VL - 766

SP - 24

EP - 29

JO - Journal of Electroanalytical Chemistry

JF - Journal of Electroanalytical Chemistry

SN - 0022-0728

ER -