Aspects of structural thiohydroxamate chemistry—on a systematic in the 5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione series

Autor:	Ingrid Svoboda, Uwe Bergsträßer, Nina Schneiders, Kristina Daniel, Hartmut Fuess, Jens Hartung
Rok vydání:	2009
Předmět:	Steric effects Strain (chemistry) Stereochemistry Organic Chemistry Substituent chemistry.chemical_element Crystal structure Free-energy relationship Biochemistry Medicinal chemistry Oxygen chemistry.chemical_compound Molecular geometry chemistry Drug Discovery X-ray crystallography
Zdroj:	Tetrahedron. 65:2567-2573
ISSN:	0040-4020
Popis:	Bond angles at thiohydroxamate oxygen in crystal structures of 3-alkoxy-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thiones gradually increased with the size of the 3-alkoxy substituent. This effect was attributed to strain on the basis of (i) a linear free energy relationship (Taft–Dubois correlation) and (ii) signal coalescence from resonances of diastereotopic CH3 groups in solution (O-cumyl substituent; DNMR). Substitution at oxygen along the sequence OR (R=prim-, sec-, and tert-alkyl), OH, and OLi was reflected in a gradual decrease of N,O distances and lengthening of associated C,S bonds. The responsivity for these changes was more pronounced in the thiazole-2(3H)-thione than in the pyridine-2(1H)-thione series.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::77e2c8b73ca0f498c4fa0b5963fe8013 https://doi.org/10.1016/j.tet.2009.01.067 Zobrazit plný text záznamu Full Text from ScienceDirect