Abstract
A method is proposed for the quantitative evaluation of the relative hydride lability of hydrogen in a number of compounds from the hydride ion affinity of the corresponding cations. The relative labilities of H− in 4H- and 2H-thiapyrans, 4H- and 2H-pyrans, 2H-thiapyran 1,1-dioxide, cyclopentadiene, and cycloheptatriene were determined by the CNDO/2 (complete neglect of differential overlap) method. It is shown that the thiapyran and pyran heterorings are distinguished by high hydride lability of hydrogen; this is evidently the principal reason for their ability to undergo disproportionation. It was established that cycloheptatriene should be a more active hydride-ion donor in nonpolar media. Correlation of the acidities of the examined compounds with the proton affinity of the corresponding anions, calculated by the CNDO/2 method, was noted.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1206–1208, September, 1977
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Pronin, A.F., Kharchenko, V.G. Quantum-chemical study of the hydride lability of hydrogen in thiapyrans and related compounds. Chem Heterocycl Compd 13, 973–975 (1977). https://doi.org/10.1007/BF00472449
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DOI: https://doi.org/10.1007/BF00472449