DFT study of molecular structure of 2-oxo-1,2,3,4-tetrahydropyrimidin-5- carboxamides and their corresponding oxidized forms 2-oxo-1,2-dihydropyrimidin- 5-carboxamides

Hamid Reza Memarian; Hassan Sabzyan; Mousa Soleymani; Mohammad Hossein Habibi; Takayoshi Suzuki

doi:10.1016/j.molstruc.2011.05.017

DFT study of molecular structure of 2-oxo-1,2,3,4-tetrahydropyrimidin-5- carboxamides and their corresponding oxidized forms 2-oxo-1,2-dihydropyrimidin- 5-carboxamides

Hamid Reza Memarian, Hassan Sabzyan, Mousa Soleymani, Mohammad Hossein Habibi, Takayoshi Suzuki

Research Institute for Interdisciplinary Science

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

16 Citations (Scopus)

Abstract

Density functional theory (DFT) at B3LYP/6-31++G^** level has been applied to study structural, electronic and bonding characteristics of some 2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxamides (THPMs) and their oxidized forms 2-oxo-1,2-dihydropyrimidin-5-carboxamides (DHPMs). Results of this study show that for these THPMs, the six-member ring adopts a boat conformation with a pseudo-axial orientation of the C₄- substituent. Experimental and theoretical ¹H NMR data obtained for THPMs and their corresponding oxidized forms (DHPMs) are correlated. Thermochemical analysis on THPMs and their corresponding oxidation products show that the oxidation reaction of THPMs to DHPMs is endothermic.

Original language	English
Pages (from-to)	91-98
Number of pages	8
Journal	Journal of Molecular Structure
Volume	998
Issue number	1-3
DOIs	https://doi.org/10.1016/j.molstruc.2011.05.017
Publication status	Published - Jul 13 2011

Keywords

2-Oxo-1,2,3,4-tetrahydropyrimidin-5-carboxamides
B3LYP/6-31++G
Conformational analysis
Crystal structure
Tetrahydropyrimidinones
X-ray diffraction

ASJC Scopus subject areas

Analytical Chemistry
Spectroscopy
Organic Chemistry
Inorganic Chemistry

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10.1016/j.molstruc.2011.05.017

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DFT study of molecular structure of 2-oxo-1,2,3,4-tetrahydropyrimidin-5- carboxamides and their corresponding oxidized forms 2-oxo-1,2-dihydropyrimidin- 5-carboxamides. / Memarian, Hamid Reza; Sabzyan, Hassan; Soleymani, Mousa; Habibi, Mohammad Hossein; Suzuki, Takayoshi.

In: Journal of Molecular Structure, Vol. 998, No. 1-3, 13.07.2011, p. 91-98.

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

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abstract = "Density functional theory (DFT) at B3LYP/6-31++G** level has been applied to study structural, electronic and bonding characteristics of some 2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxamides (THPMs) and their oxidized forms 2-oxo-1,2-dihydropyrimidin-5-carboxamides (DHPMs). Results of this study show that for these THPMs, the six-member ring adopts a boat conformation with a pseudo-axial orientation of the C4- substituent. Experimental and theoretical 1H NMR data obtained for THPMs and their corresponding oxidized forms (DHPMs) are correlated. Thermochemical analysis on THPMs and their corresponding oxidation products show that the oxidation reaction of THPMs to DHPMs is endothermic.",

keywords = "2-Oxo-1,2,3,4-tetrahydropyrimidin-5-carboxamides, B3LYP/6-31++G, Conformational analysis, Crystal structure, Tetrahydropyrimidinones, X-ray diffraction",

author = "Memarian, {Hamid Reza} and Hassan Sabzyan and Mousa Soleymani and Habibi, {Mohammad Hossein} and Takayoshi Suzuki",

note = "Funding Information: We are thankful to the Center of Excellence (Chemistry), Research Council and Office of Graduate Studies of the University of Isfahan for their financial support. ",

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doi = "10.1016/j.molstruc.2011.05.017",

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AU - Memarian, Hamid Reza

AU - Sabzyan, Hassan

AU - Soleymani, Mousa

AU - Habibi, Mohammad Hossein

AU - Suzuki, Takayoshi

N1 - Funding Information: We are thankful to the Center of Excellence (Chemistry), Research Council and Office of Graduate Studies of the University of Isfahan for their financial support.

PY - 2011/7/13

Y1 - 2011/7/13

N2 - Density functional theory (DFT) at B3LYP/6-31++G** level has been applied to study structural, electronic and bonding characteristics of some 2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxamides (THPMs) and their oxidized forms 2-oxo-1,2-dihydropyrimidin-5-carboxamides (DHPMs). Results of this study show that for these THPMs, the six-member ring adopts a boat conformation with a pseudo-axial orientation of the C4- substituent. Experimental and theoretical 1H NMR data obtained for THPMs and their corresponding oxidized forms (DHPMs) are correlated. Thermochemical analysis on THPMs and their corresponding oxidation products show that the oxidation reaction of THPMs to DHPMs is endothermic.

AB - Density functional theory (DFT) at B3LYP/6-31++G** level has been applied to study structural, electronic and bonding characteristics of some 2-oxo-1,2,3,4-tetrahydropyrimidin-5-carboxamides (THPMs) and their oxidized forms 2-oxo-1,2-dihydropyrimidin-5-carboxamides (DHPMs). Results of this study show that for these THPMs, the six-member ring adopts a boat conformation with a pseudo-axial orientation of the C4- substituent. Experimental and theoretical 1H NMR data obtained for THPMs and their corresponding oxidized forms (DHPMs) are correlated. Thermochemical analysis on THPMs and their corresponding oxidation products show that the oxidation reaction of THPMs to DHPMs is endothermic.

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KW - X-ray diffraction

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DFT study of molecular structure of 2-oxo-1,2,3,4-tetrahydropyrimidin-5- carboxamides and their corresponding oxidized forms 2-oxo-1,2-dihydropyrimidin- 5-carboxamides

Abstract

Keywords

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