Acetaldehyde-Ammonia Interaction

A DFT Study of Reaction Mechanism and Product Identification

Vera P. Tuguldurova, Alexander V. Fateev, Victor S. Malkov, Oleg Kh Poleshchuk, Olga V. Vodyankina

    Research output: Contribution to journalArticle

    2 Citations (Scopus)

    Abstract

    The product of acetaldehyde and ammonia reaction, namely, 2,4,6-trimethyl-1,3,5-hexahydrotriazine trihydrate, was synthesized and identified using a combination of experimental (NMR spectroscopy, IR spectroscopy, melting point determination) and DFT-based theoretical approaches. A reaction mechanism was proposed. The reaction was shown to proceed via the formation of aminoalcohol, imine, and geminal diamine intermediates accompanied by cyclization of these species. The calculation results allowed us to build a potential energy surface of the acetaldehyde and ammonia interaction and determine the most energetically favorable pathway to yield acetaldehyde ammonia trimer. The reaction product was found in an energy minimum (-53.5 kcal/mol).

    Original languageEnglish
    Pages (from-to)3136-3141
    Number of pages6
    JournalJournal of Physical Chemistry A
    Volume121
    Issue number16
    DOIs
    Publication statusPublished - 27 Apr 2017

    Fingerprint

    Acetaldehyde
    acetaldehyde
    Ammonia
    Discrete Fourier transforms
    ammonia
    products
    Potential energy surfaces
    Imines
    Diamines
    Cyclization
    interactions
    diamines
    trimers
    Reaction products
    reaction products
    imines
    spectroscopy
    Nuclear magnetic resonance spectroscopy
    melting points
    Melting point

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry

    Cite this

    Tuguldurova, V. P., Fateev, A. V., Malkov, V. S., Poleshchuk, O. K., & Vodyankina, O. V. (2017). Acetaldehyde-Ammonia Interaction: A DFT Study of Reaction Mechanism and Product Identification. Journal of Physical Chemistry A, 121(16), 3136-3141. https://doi.org/10.1021/acs.jpca.7b00823

    Acetaldehyde-Ammonia Interaction : A DFT Study of Reaction Mechanism and Product Identification. / Tuguldurova, Vera P.; Fateev, Alexander V.; Malkov, Victor S.; Poleshchuk, Oleg Kh; Vodyankina, Olga V.

    In: Journal of Physical Chemistry A, Vol. 121, No. 16, 27.04.2017, p. 3136-3141.

    Research output: Contribution to journalArticle

    Tuguldurova, VP, Fateev, AV, Malkov, VS, Poleshchuk, OK & Vodyankina, OV 2017, 'Acetaldehyde-Ammonia Interaction: A DFT Study of Reaction Mechanism and Product Identification', Journal of Physical Chemistry A, vol. 121, no. 16, pp. 3136-3141. https://doi.org/10.1021/acs.jpca.7b00823
    Tuguldurova, Vera P. ; Fateev, Alexander V. ; Malkov, Victor S. ; Poleshchuk, Oleg Kh ; Vodyankina, Olga V. / Acetaldehyde-Ammonia Interaction : A DFT Study of Reaction Mechanism and Product Identification. In: Journal of Physical Chemistry A. 2017 ; Vol. 121, No. 16. pp. 3136-3141.
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