Acid ? Base properties of 3,4-dimethyl-2-thiazolone, 4-methyl-2-thiazolone, and 5-acetyl-4-methyl-2-thiazolone

Autor:	O. V. Maksimova, V. I. Zaionts, M. G. Mints
Rok vydání:	1972
Předmět:	chemistry.chemical_classification Acylation chemistry.chemical_compound chemistry Base (chemistry) Organic Chemistry Organic chemistry Molecule Protonation Thiazole Medicinal chemistry Orders of magnitude (mass) Derivative (chemistry)
Zdroj:	Chemistry of Heterocyclic Compounds. 8:1471-1474
ISSN:	1573-8353 0009-3122
DOI:	10.1007/bf00471832
Popis:	In contrast to 2-methoxy-4-methylthiazole and 2,4-dimethylthiazole, the protonation of 3,4-dimethyl-2-thiazolone does not proceed in media with acidities up to H0=−3.99. The acidity of N-H increases by 2.4 orders of magnitude on passing from 4-methyl-2-thiazolone to its 5-acetyl derivative. The data obtained from a study of the acid-base properties in conjunction with the results of calculations of the 3,4-dimethyl-2-thiazolone and thiazole molecules by the MO method make it possible to conclude that there is a δ charge in the 5 position of 2-thiazolones and that this is the reason for the facile acylation of these compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::51e0d1601ad3acb8a3c6c6e419f50843 https://doi.org/10.1007/bf00471832 Zobrazit plný text záznamu Full text from SpringerLink