Abstract
A significat (≈85 ppm) increase in shielding of the15N nucleus is observed in the successive series of 10, 12, and 14 π-electron heterocycles: 2,1,3-benzothiadiazole, 1,3,2,4-benzodithiadiazine, and 1,3,5,2,4-benzotrithiadiazine, as compared to the gain from both the full and the π-charge of the nitrogen atom. Possible antiaromaticity of the 12 π-electron dithiadiazine, containing a low-lying activation state, does not appear clearly in the15N NMR.
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Additional information
Part IX in the series “Cyclin Aryleneazachalcogenins.” For Part VIII, cf. [1].
Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 262–265, February, 1995. Original article submitted February 14, 1995.
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Shakirov, M.M., Beregovaya, I.V. & Zibarev, A.V. Gain in magnetic shielding of the15N nucleus in a successive series of related 10, 12, and 14 π-electron heterocycles: 2,1,3-bensothiadiazole, 1,3,2,4-benzodithiadiazine, and 1,3,5,2,4-benzotrithiadiazine. Chem Heterocycl Compd 31, 231–234 (1995). https://doi.org/10.1007/BF01169686
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DOI: https://doi.org/10.1007/BF01169686