Acetaldehyde-Ammonia Interaction: A DFT Study of Reaction Mechanism and Product Identification

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 language	English
Pages (from-to)	3136-3141
Number of pages	6
Journal	Journal of Physical Chemistry A
Volume	121
Issue number	16
DOIs	https://doi.org/10.1021/acs.jpca.7b00823
Publication status	Published - 27 Apr 2017

ASJC Scopus subject areas

Physical and Theoretical Chemistry

Access to Document

10.1021/acs.jpca.7b00823

Fingerprint Dive into the research topics of 'Acetaldehyde-Ammonia Interaction: A DFT Study of Reaction Mechanism and Product Identification'. Together they form a unique fingerprint.

Cite this

@article{a404695cfb41497caae3d246d06b8acf,

title = "Acetaldehyde-Ammonia Interaction: A DFT Study of Reaction Mechanism and Product Identification",

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).",

author = "Tuguldurova, {Vera P.} and Fateev, {Alexander V.} and Malkov, {Victor S.} and Poleshchuk, {Oleg Kh} and Vodyankina, {Olga V.}",

year = "2017",

month = apr,

day = "27",

doi = "10.1021/acs.jpca.7b00823",

language = "English",

volume = "121",

pages = "3136--3141",

journal = "Journal of Physical Chemistry A",

issn = "1089-5639",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Acetaldehyde-Ammonia Interaction

T2 - A DFT Study of Reaction Mechanism and Product Identification

AU - Tuguldurova, Vera P.

AU - Fateev, Alexander V.

AU - Malkov, Victor S.

AU - Poleshchuk, Oleg Kh

AU - Vodyankina, Olga V.

PY - 2017/4/27

Y1 - 2017/4/27

N2 - 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).

AB - 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).

UR - http://www.scopus.com/inward/record.url?scp=85020170015&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85020170015&partnerID=8YFLogxK

U2 - 10.1021/acs.jpca.7b00823

DO - 10.1021/acs.jpca.7b00823

M3 - Article

AN - SCOPUS:85020170015

VL - 121

SP - 3136

EP - 3141

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

SN - 1089-5639

IS - 16

ER -