Intramolecular fixation of t-butyl groups in thiolactim ethers influencing molecular conformation and the packing behavior

Autor:	Jens Kortus, Thomas Gruber, Jörg Hübscher, Edwin Weber, Wilhelm Seichter
Rok vydání:	2015
Předmět:	Hydrogen bond Stereochemistry Organic Chemistry Molecular conformation Analytical Chemistry Inorganic Chemistry Pyridazine Azine chemistry.chemical_compound chemistry Intramolecular force Molecular stability Pyridine Density functional theory Spectroscopy
Zdroj:	Journal of Molecular Structure. 1091:88-97
ISSN:	0022-2860
DOI:	10.1016/j.molstruc.2015.02.064
Popis:	Derived from the result of a previous crystallographic study regarding an ethynylene bridged bispyrimidine, the presence of two intramolecular C–H⋯N hydrogen bonding contacts being responsible for a fixation of the terminal t-butylthio units to the azine nitrogens was noticed. Acting as stimulus, a series of different pyridine and pyridazine derivatives also featuring this unusual functionality has been synthesized and structurally studied. In order to support the investigations concerning this particular bonding pattern performed via X-ray structure analysis, calculations based on the density functional theory were carried out. It was found that the formation of the intramolecular hydrogen bonding motif has not only impact on the molecular stability but in some cases also predictably influences the reactivity and the packing behavior of the different heterocycles.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::abd2e77e2744930fe38fbf6346229155 https://doi.org/10.1016/j.molstruc.2015.02.064 Zobrazit plný text záznamu Full Text from ScienceDirect