Synthesis and tautomerism study of 6-benzoylmethyl-1,3,5-triazin-2,4- diamine

Nikhil Sachdeva; Anton V. Dolzhenko; Wai Keung Chui

doi:10.1016/j.crci.2010.10.003

Synthesis and tautomerism study of 6-benzoylmethyl-1,3,5-triazin-2,4- diamine

Nikhil Sachdeva, Anton V. Dolzhenko, Wai Keung Chui

Research output: Contribution to journal › Article › Research › peer-review

4 Citations (Scopus)

Abstract

From the reaction of biguanide with ethyl benzoylacetate, N-(6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)guanidine (1) and 6-benzoylmethyl-1,3,5-triazin-2,4-diamine (2) were isolated. The structural evaluation of 2 was performed theoretically (DFT calculations) and experimentally (NMR spectroscopy and X-ray crystallography). The effects of solvents and temperature on keto-enol-enaminone tautomeric equilibrium were explored.

Original language	English
Pages (from-to)	580-587
Number of pages	8
Journal	Comptes Rendus Chimie
Volume	14
Issue number	6
DOIs	https://doi.org/10.1016/j.crci.2010.10.003
Publication status	Published - Jun 2011
Externally published	Yes

Keywords

DFT calculations
Resonance-assisted hydrogen bonding
Solvent effect
Tautomerism
Triazines
X-ray crystal structure

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10.1016/j.crci.2010.10.003

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title = "Synthesis and tautomerism study of 6-benzoylmethyl-1,3,5-triazin-2,4- diamine",

abstract = "From the reaction of biguanide with ethyl benzoylacetate, N-(6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)guanidine (1) and 6-benzoylmethyl-1,3,5-triazin-2,4-diamine (2) were isolated. The structural evaluation of 2 was performed theoretically (DFT calculations) and experimentally (NMR spectroscopy and X-ray crystallography). The effects of solvents and temperature on keto-enol-enaminone tautomeric equilibrium were explored.",

keywords = "DFT calculations, Resonance-assisted hydrogen bonding, Solvent effect, Tautomerism, Triazines, X-ray crystal structure",

author = "Nikhil Sachdeva and Dolzhenko, \{Anton V.\} and Chui, \{Wai Keung\}",

note = "Funding Information: This work is supported by Academic Research Fund (WBS R-148-000-069-112) from the National University of Singapore. One of the authors (N.S.) thanks the National University of Singapore for a research scholarship. We also acknowledge Geok Kheng Tan and Lip Lin Koh (Chemistry, NUS) for crystallographic support. The authors also wish to acknowledge help of Janardan Krishnamurthy (DBS, NUS) and Krishnan Chandrashekharan (Chemistry, NUS). Copyright: Copyright 2011 Elsevier B.V., All rights reserved.",

year = "2011",

month = jun,

doi = "10.1016/j.crci.2010.10.003",

language = "English",

volume = "14",

pages = "580--587",

journal = "Comptes Rendus Chimie",

issn = "1631-0748",

publisher = "Academie des Sciences",

number = "6",

}

TY - JOUR

T1 - Synthesis and tautomerism study of 6-benzoylmethyl-1,3,5-triazin-2,4- diamine

AU - Sachdeva, Nikhil

AU - Dolzhenko, Anton V.

AU - Chui, Wai Keung

N1 - Funding Information: This work is supported by Academic Research Fund (WBS R-148-000-069-112) from the National University of Singapore. One of the authors (N.S.) thanks the National University of Singapore for a research scholarship. We also acknowledge Geok Kheng Tan and Lip Lin Koh (Chemistry, NUS) for crystallographic support. The authors also wish to acknowledge help of Janardan Krishnamurthy (DBS, NUS) and Krishnan Chandrashekharan (Chemistry, NUS). Copyright: Copyright 2011 Elsevier B.V., All rights reserved.

PY - 2011/6

Y1 - 2011/6

N2 - From the reaction of biguanide with ethyl benzoylacetate, N-(6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)guanidine (1) and 6-benzoylmethyl-1,3,5-triazin-2,4-diamine (2) were isolated. The structural evaluation of 2 was performed theoretically (DFT calculations) and experimentally (NMR spectroscopy and X-ray crystallography). The effects of solvents and temperature on keto-enol-enaminone tautomeric equilibrium were explored.

AB - From the reaction of biguanide with ethyl benzoylacetate, N-(6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)guanidine (1) and 6-benzoylmethyl-1,3,5-triazin-2,4-diamine (2) were isolated. The structural evaluation of 2 was performed theoretically (DFT calculations) and experimentally (NMR spectroscopy and X-ray crystallography). The effects of solvents and temperature on keto-enol-enaminone tautomeric equilibrium were explored.

KW - DFT calculations

KW - Resonance-assisted hydrogen bonding

KW - Solvent effect

KW - Tautomerism

KW - Triazines

KW - X-ray crystal structure

UR - https://www.scopus.com/pages/publications/79958841788

U2 - 10.1016/j.crci.2010.10.003

DO - 10.1016/j.crci.2010.10.003

M3 - Article

AN - SCOPUS:79958841788

SN - 1631-0748

VL - 14

SP - 580

EP - 587

JO - Comptes Rendus Chimie

JF - Comptes Rendus Chimie

IS - 6

ER -

Synthesis and tautomerism study of 6-benzoylmethyl-1,3,5-triazin-2,4- diamine

Abstract

Keywords

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