Abstract
Sixteen 4-arylthiazol-2(3H)-ones (3) were synthesised by cyclisation of α-thiocyanatoacetophenones (1) in acid solution. They appear to prefer greatly the oxo tautomeric forms. In CCl4 solution an equilibrium between the free CO bond and a “dimeric” hydrogen-bonded form exists in which the latter predominates. Several IR and NMR (1H, 13C and 15N) spectral properties are shown to correlate with Hammett σ-values and/or atomic Mulliken charges and bond orders, the latter being estimated by PM3 or AM1 semiempirical methods. The electron-impact mass spectra were also recorded and the fragmentation mechanisms interpreted in terms of the energetics of the ionic species. In addition, the geometric and electronic properties of 4-phenylthiazol-2(3H)-one (3a) and the related benzothiazol-2(3H)-one (4) based on ab initio HF/6-31 G* calculations are compared with each other.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
