An infrared study of rotational isomerism in thiazole-2-carboxylates was written by Kaye, Perry T.;Meakins, G. Denis;Willbe, Charles;Williams, Peter R.. And the article was included in Journal of the Chemical Society in 1981.Reference of 79247-77-1 The following contents are mentioned in the article:
Twenty-five alkyl thiazole-2-carboxylates with a range of 4- and 5-substituents were prepared through the Hantzsch synthesis. E.g., cyclocondensation reaction of (H2N)2CS with MeCOCH2Br followed by bromination, oxidation, and alkylation gave the thiazole esters I (R = Me, Et). Solutions of these esters show well resolved doublets in the carbonyl IR spectra, due to rotational isomers. The higher wave number components were assigned to the more polar carbonyl O,S-anti-s-trans rotamers and those at lower wave number to the O,S-syn-s-trans forms. Small, but systematic, differences between the Me esters were noted. This study involved multiple reactions and reactants, such as 5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide (cas: 79247-77-1Reference of 79247-77-1).
5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide (cas: 79247-77-1) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Reference of 79247-77-1
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica