A simple and efficient synthesis and dynamic NMR studies of some new podands of dithiocarbamates formed from bis(naphthyl) derivatives
✍ Scribed by Abbas Shockravi; Mahmood Kamali; Farhad Sorkhei; Reza Jafari
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 210 KB
- Volume
- 22
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20730
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✦ Synopsis
The reaction of dithiocarbamate salts (IV a-c ) with bis(naphthalene chloroacetates) (II a,b ) and bis(naphthalene ethoxybromide) (II c ) in dimethylformamide (DMF) furnished corresponding podands as V a-i in high to excellent yields. Three reacting ligands, (II a,b ) and (II c ), were obtained in the reaction of bis(naphthalene) (I a,b ) with chloroacetylchloride and 1,2-dibromoethane. Dynamic NMR spectroscopic data of three series of podands (V a-c , V d-f , and V g-i ) are discussed, and their free energy of activation ( G = C ) at coalescence temperatures are figured out. The G =
C s of these podands were attributed to conformational isomerization in the range of 14.5-18.3 kcal mol -1 due to rotation and resonance effects about thioamide C N bond.