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Quantum-chemical study of isocyanate reactions with linear methanol associates: IX. Methyl isocyanate reaction with methanol-phenol complexes

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Abstract

Quantum-chemical method B3LYP/6-311++G(df,p) was applied to the study of complex formation between phenol and methanol. The complexes of molecules bound by the hydrogen bond possess enhanced donoracceptor and acid-base properties as compared to monomer molecules. The reactions of phenol and methanol complexes with methyl isocyanate proceed through a concerted late asymmetric transition state by the type of nucleophilic addition. The most kinetically and thermodynamically favorable transformation is the process involving the complex “phenol-acceptor, methanol-donor.” Phenol compounds are able to catalyze the addition of alcohols to isocyanates.

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Authors and Affiliations

  1. Kazan National Research Technological University, Kazan, 420015, Russia

    A. Ya. Samuilov, S. V. Nesterov, F. B. Balabanova & Ya. D. Samuilov

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

    A. I. Konovalov

Authors
  1. A. Ya. Samuilov
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  2. S. V. Nesterov
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  3. F. B. Balabanova
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  4. Ya. D. Samuilov
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  5. A. I. Konovalov
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Correspondence to Ya. D. Samuilov.

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Original English Text © A.Ya. Samuilov, S.V. Nesterov, F.B. Balabanova, Ya.D. Samuilov, A.I. Konovalov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 167–171.

For communication VIII, see [1].

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Samuilov, A.Y., Nesterov, S.V., Balabanova, F.B. et al. Quantum-chemical study of isocyanate reactions with linear methanol associates: IX. Methyl isocyanate reaction with methanol-phenol complexes. Russ J Org Chem 50, 155–159 (2014). https://doi.org/10.1134/S1070428014020018

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  • DOI: https://doi.org/10.1134/S1070428014020018

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