A Simple and Eco-Compatible One-Pot Synthesis of New Symmetrical Dithiocarbamate Podands and Their Dynamic NMR Studies |
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Authors: | Abbas Shockravi Mahmood Kamali Reza Jafari |
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Institution: | Faculty of Chemistry , Kharazmi (Tarbiat Moallem) University , Tehran , Iran |
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Abstract: | Abstract A simple and eco-compatible synthesis of podands as 4a-i is performed using amines (3a-c ), CS2, and dichlordiamides (DCDs) (2a, c ) in the absence of a catalyst in water. Three reacting DCDs (2a-c ) were obtained in the reaction of aromatic diamines (1a, c ) with chloroacetyl chloride. Dynamic NMR spectroscopic data of three series of podands (4a-c , 4d-f , and 4g-i ) are discussed and their free energies of activations are calculated (ΔG ≠ c s) at coalescence temperatures. The ΔG ≠ c of these podands were attributed to conformational isomerization in the range of 14.7–17 kcal/mol due to rotation and resonance effects about the thioamide C?N bond. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures.] |
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Keywords: | Podand didithiocarbamate reaction in water aromatic diamines dynamic NMR free energies of activation (ΔG≠) |
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