Effect of Electron-Withdrawing Substituents on the Epoxide Ring: An Experimental and Theoretical Electron Density Analysis of a Series of Epoxide Derivatives

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Simon Grabowsky
  • Tanja Schirmeister
  • Carsten Paulmann
  • Thomas Pfeuffer
  • Peter Luger
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000287636200011&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1021/jo102125n
eISSN
1520-6904
Externe Identifier
  • Clarivate Analytics Document Solution ID: 725HQ
  • PubMed Identifier: 21250719
ISSN
0022-3263
Ausgabe der Veröffentlichung
5
Zeitschrift
JOURNAL OF ORGANIC CHEMISTRY
Paginierung
1305 - 1318
Datum der Veröffentlichung
2011
Status
Published
Titel
Effect of Electron-Withdrawing Substituents on the Epoxide Ring: An Experimental and Theoretical Electron Density Analysis of a Series of Epoxide Derivatives
Sub types
  • Article
Ausgabe der Zeitschrift
76

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Autoren
  • Simon Grabowsky
  • Tanja Schirmeister
  • Carsten Paulmann
  • Thomas Pfeuffer
  • Peter Luger
DOI
10.1021/jo102125n
eISSN
1520-6904
ISSN
0022-3263
Ausgabe der Veröffentlichung
5
Zeitschrift
The Journal of Organic Chemistry
Sprache
en
Online publication date
2011
Paginierung
1305 - 1318
Datum der Veröffentlichung
2011
Status
Published
Herausgeber
American Chemical Society (ACS)
Herausgeber URL
http://dx.doi.org/10.1021/jo102125n
Datum der Datenerfassung
2023
Titel
Effect of Electron-Withdrawing Substituents on the Epoxide Ring: An Experimental and Theoretical Electron Density Analysis of a Series of Epoxide Derivatives
Ausgabe der Zeitschrift
76

Datenquelle: Crossref

Abstract
A series of acceptor-substituted epoxide derivatives is scrutinized by means of experimental and theoretical electron-density investigations. Due to the possibility of nucleophilic ring-opening, the epoxide ring is not only a very useful functional group in organic synthesis, but acceptor-substituted epoxides are valuable building blocks for the design of protease inhibitors. Therefore, the electron-density analysis in this work focuses on two main aspects that can contribute to rational drug design: (i) the quantification of the electron-withdrawing substituent effects on the epoxide ring and (ii) the intermolecular interactions involving the epoxide ring in combination with different substituents. It can be shown that the electron-withdrawing properties of the substituents cause an elongation of the C-C bonds in the epoxide rings and the loss of electron density can be measured by an analysis of critical points, atomic charges, and the source function. The different strengths of the substituents are reflected in these properties. Covalent and electrostatic contributions to the intermolecular interactions and thus the lattice energies are depicted on different molecular surfaces.
Addresses
  • Freie Universität Berlin, Institut für Chemie und Biochemie/Anorganische Chemie, Fabeckstr. 36a, 14195 Berlin, Germany. vongrabo@chemie.fu-berlin.de
Autoren
  • Simon Grabowsky
  • Tanja Schirmeister
  • Carsten Paulmann
  • Thomas Pfeuffer
  • Peter Luger
DOI
10.1021/jo102125n
eISSN
1520-6904
Externe Identifier
  • PubMed Identifier: 21250719
Open access
false
ISSN
0022-3263
Ausgabe der Veröffentlichung
5
Zeitschrift
The Journal of organic chemistry
Schlüsselwörter
  • Epoxy Compounds
  • Crystallography, X-Ray
  • Molecular Structure
  • Stereoisomerism
  • Electrons
  • Quantum Theory
  • Models, Molecular
Sprache
eng
Medium
Print-Electronic
Online publication date
2011
Paginierung
1305 - 1318
Datum der Veröffentlichung
2011
Status
Published
Datum der Datenerfassung
2011
Titel
Effect of electron-withdrawing substituents on the epoxide ring: an experimental and theoretical electron density analysis of a series of epoxide derivatives.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
76

Datenquelle: Europe PubMed Central

Abstract
A series of acceptor-substituted epoxide derivatives is scrutinized by means of experimental and theoretical electron-density investigations. Due to the possibility of nucleophilic ring-opening, the epoxide ring is not only a very useful functional group in organic synthesis, but acceptor-substituted epoxides are valuable building blocks for the design of protease inhibitors. Therefore, the electron-density analysis in this work focuses on two main aspects that can contribute to rational drug design: (i) the quantification of the electron-withdrawing substituent effects on the epoxide ring and (ii) the intermolecular interactions involving the epoxide ring in combination with different substituents. It can be shown that the electron-withdrawing properties of the substituents cause an elongation of the C-C bonds in the epoxide rings and the loss of electron density can be measured by an analysis of critical points, atomic charges, and the source function. The different strengths of the substituents are reflected in these properties. Covalent and electrostatic contributions to the intermolecular interactions and thus the lattice energies are depicted on different molecular surfaces.
Autoren
  • Simon Grabowsky
  • Tanja Schirmeister
  • Carsten Paulmann
  • Thomas Pfeuffer
  • Peter Luger
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/21250719
DOI
10.1021/jo102125n
eISSN
1520-6904
Ausgabe der Veröffentlichung
5
Zeitschrift
J Org Chem
Schlüsselwörter
  • Crystallography, X-Ray
  • Electrons
  • Epoxy Compounds
  • Models, Molecular
  • Molecular Structure
  • Quantum Theory
  • Stereoisomerism
Sprache
eng
Country
United States
Paginierung
1305 - 1318
Datum der Veröffentlichung
2011
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2011
Titel
Effect of electron-withdrawing substituents on the epoxide ring: an experimental and theoretical electron density analysis of a series of epoxide derivatives.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
76

Datenquelle: PubMed

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