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Kinetics and mechanism of reaction of cis-α,β-dinitrostilbene with morpholine

  • Physical Chemistry
  • Kinetics. Chemical Equilibrium
  • Published:
Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

Reaction of cis-α,β-dinitrostilbene (substrate) with morpholine (reagent) in n-hexane leads to cis-α-nitro-β-morpholinostilbene (end product). The process is of first order with respect to the substrate and second order with respect to the reagent. Possible reaction mechanisms are analyzed, and it is established that the following are most probable on the basis of kinetic patterns and stereochemistry: development of a charge transfer complex having a hydrogen bond between the substrate nitro group and reagent amino group; reaction of the complex with a second reagent molecule and formation of a carbanion (this stage determines the overall reaction rate); and detachment of a nitrite ion from the nitrocarbanion and its protonation to form the end product.

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Authors
  1. S. V. Koroteev
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  2. D. S. Ermekov
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  3. Z. V. Todres
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  4. A. D. Malievskii
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Additional information

N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 117977 Moscow. A. N. Nesmeyanov Institute of Heteroorganic Compound, Russian Academy of Sciences, 117813 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 78–83, January, 1992.

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Koroteev, S.V., Ermekov, D.S., Todres, Z.V. et al. Kinetics and mechanism of reaction of cis-α,β-dinitrostilbene with morpholine. Russ Chem Bull 41, 60–64 (1992). https://doi.org/10.1007/BF00863913

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  • DOI: https://doi.org/10.1007/BF00863913

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