Strong intramolecular hydrogen bonds and steric effects involving C═S groups An NMR and computational study

Strong intramolecular hydrogen bonds and steric effects involving C═S groups : An NMR and computational study

© 2019 John Wiley & Sons, Ltd.

Bibliographische Detailangaben
Veröffentlicht in:Magnetic resonance in chemistry : MRC. - 1985. - 58(2020), 2 vom: 27. Feb., Seite 154-162
1. Verfasser: Elias, Rita S (VerfasserIn)
Weitere Verfasser: Saeed, Bahjat A, Kamounah, Fadhil S, Duus, Fritz, Hansen, Poul Erik
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2020
Zugriff auf das übergeordnete Werk:Magnetic resonance in chemistry : MRC
Schlagworte:Journal Article Research Support, Non-U.S. Gov't adamantyl derivatives intramolecular hydrogen bonding isotope effects steric effects thiorhodanines
Beschreibung
Zusammenfassung:© 2019 John Wiley & Sons, Ltd.
A number of 5-acyl rhodanines and thiorhodanines with bulky acyl groups (pivaloyl and adamantoyl), not previously available, have been synthesized. The compounds are shown to exist in the enol form. Structures have been calculated using both the MP2 approach and the B3LYP-GD3BJ functional and the 6-311++G(d,p) basis set. Hydrogen bond energies are estimated by subtracting energies of a structure with the OH group turned 180° from those of the intramolecularly hydrogen-bonded one. Properties such as OH chemical shifts, two-bond isotope effects on 13 C chemical shifts, electron densities at the bond critical point from atoms in molecules analysis, and the hydrogen bond energies show that the sterically hindered compounds have stronger hydrogen bonds than methyl or isopropyl derivatives. The combination of oxygen and sulfur derivatives enables a detailed analysis of hydrogen bond energies
Beschreibung:Date Completed 27.01.2020
Date Revised 27.01.2020
published: Print-Electronic
Citation Status PubMed-not-MEDLINE
ISSN:1097-458X
DOI:10.1002/mrc.4959