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Literature DB >> 19726857

2-Amino-3-methyl-6-[methyl(phenyl)amino]-5-nitropyrimidin-4(3H)-one: polarized molecules within hydrogen-bonded sheets.

Ricaurte Rodríguez¹, Manuel Nogueras, Justo Cobo, Christopher Glidewell.

Abstract

The pyrimidinone ring in the title compound, C(12)H(13)N(5)O(3), is effectively planar, despite the presence of five substituents. The bond distances provide evidence for significant polarization of the electronic structure, with charge separation, and the molecules are linked into sheets by a combination of N-H...O and N-H...pi(arene) hydrogen bonds. Comparisons are made with the molecular and supramolecular structures of the precursor compound 2-amino-6-[methyl(phenyl)amino]-5-nitropyrimidin-4(3H)-one.

Entities: Chemical

Mesh：

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Year: 2009 PMID： 19726857 PMCID： PMC2737423 DOI： 10.1107/S010827010902887X

Source DB: PubMed Journal: Acta Crystallogr C ISSN： 0108-2701 Impact factor: 1.172

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References

12 in total

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Authors: Jorge Trilleras; Jairo Quiroga; John N Low; Justo Cobo; Christopher Glidewell
Journal: Acta Crystallogr C Date: 2007-11-30 Impact factor: 1.172

2. A three-dimensional hydrogen-bonded framework in 2-amino-6-(N-methylanilino)pyrimidin-4(3H)-one and a ribbon of fused hydrogen-bonded rings in 2-amino-6-(N-methylanilino)-5-nitropyrimidin-4(3H)-one.

Authors: Ricaurte Rodríguez; Justo Cobo; Manuel Nogueras; John N Low; Christopher Glidewell
Journal: Acta Crystallogr C Date: 2007-11-14 Impact factor: 1.172

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Journal: Eur J Med Chem Date: 2001 Nov-Dec Impact factor: 6.514

4. A three-dimensional hydrogen-bonded framework in 2-amino-4,6-bis[N-methyl-N-(4-methylphenyl)amino]pyrimidine-5-carbaldehyde and hydrogen-bonded sheets in 2-amino-4-(indolin-1-yl)-6-methoxypyrimidine-5-carbaldehyde.

Authors: John N Low; Jorge Trilleras; Justo Cobo; Antonio Marchal; Christopher Glidewell
Journal: Acta Crystallogr C Date: 2007-10-24 Impact factor: 1.172

5. Symmetrically 4,6-disubstituted 2-aminopyrimidines and 2-amino-5-nitrosopyrimidines: interplay of molecular, molecular-electronic and supramolecular structures.

Authors: Antonio Quesada; Antonio Marchal; Manuel Melguizo; John N Low; Christopher Glidewell
Journal: Acta Crystallogr B Date: 2004-01-21

6. N6-substituted 2-amino-4-chloro-5-formylpyrimidines: puckered versus planar pyrimidine rings, and hydrogen-bonded aggregation in zero, one, two and three dimensions.

Authors: Justo Cobo; Jorge Trilleras; Jairo Quiroga; Antonio Marchal; Manuel Nogueras; John N Low; Christopher Glidewell
Journal: Acta Crystallogr B Date: 2008-09-15

7. 2-Amino-4-chloro-5-formyl-6-[methyl(2-methylphenyl)amino]pyrimidine and 2-amino-4-chloro-5-formyl-6-[(2-methoxyphenyl)methylamino]pyrimidine are isostructural and form hydrogen-bonded sheets of R2(2)8 and R6(6)32 rings.

Authors: Jorge Trilleras; Jairo Quiroga; Justo Cobo; Christopher Glidewell
Journal: Acta Crystallogr C Date: 2008-12-13 Impact factor: 1.172