Supramolecular structure of 6-phenyl-2-chloropyrimidine-4-carboxamide and its complexes with dioxane and ethanol

Rybalova, Т. V.; Krivopalov, V. P.; Gatilov, Yu. V.; Nikulicheva, O. N.; Shkurko, O. P.

doi:10.1007/s10947-007-0048-2

Cited by 4 publications

(2 citation statements)

References 11 publications

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“…To illustrate, we choose the same 'carbamoyl' group type as hydrogen-bond donor. The first structure, CSD refcode TITHUA, is the structure of 2-chloro-4-amido-6-phenylpyrimidine (Rybalova et al, 2007). A hydrogen-bond dimer motif is present involving each carbamoyl group donating and accepting one hydrogen bond, respectively (Fig.…”

Section: Tablementioning

confidence: 99%

Hydrogen-bond coordination in organic crystal structures: statistics, predictions and applications

Galek

Chisholm

Pidcock

et al. 2014

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Statistical models to predict the number of hydrogen bonds that might be formed by any donor or acceptor atom in a crystal structure have been derived using organic structures in the Cambridge Structural Database. This hydrogen-bond coordination behaviour has been uniquely defined for more than 70 unique atom types, and has led to the development of a methodology to construct hypothetical hydrogen-bond arrangements. Comparing the constructed hydrogen-bond arrangements with known crystal structures shows promise in the assessment of structural stability, and some initial examples of industrially relevant polymorphs, co-crystals and hydrates are described.

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Section: Tablementioning

confidence: 99%

Hydrogen-bond coordination in organic crystal structures: statistics, predictions and applications

Galek

Chisholm

Pidcock

et al. 2014

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…There are some reports about the characterization of general pyrimidinic compounds based on NMR spectroscopy [9,10] and X-ray scattering of crystallin supramolecular structures techniques [11][12][13]. There are very few reports, however, dedicated to the structural assignement of pyrimidines based on X-ray crystallography associated with theoretical *Address correspondence to this author at the Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, CEP --97.105-900, Santa Maria, RS, Brazil; Tel: +55 55 3220 8756; Fax: +55 55 3220 8756; E-mail: zanatta@base.ufsm.br calculations or to the aromatic character quantification of such heterocycles [14][15][16] and, to the best of our knowledge, there are no studies of this nature dealing with N'-benzylidenehydrazino pyrimidines.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Aromatic Character and AM1 Calculations of 2-(N`- Benzylidenehydrazino)-4-trifluoromethyl-pyrimidine and 2-(N`-2-Methylbenzylidenehydrazino)- 5-methyl-4-trifluoromethyl-pyrimidine~!2010-02-08~!2010-05-04~!2010-06-22~!

Amaral¹,

Campos²,

Santos³

et al. 2010

TOCRYJ

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The structure of two novel 2-(N'-benzylidenehydrazino)-4-trifluoromethyl-pyrimidines has been determined by X-ray crystallography and their energy-minimized structures were stablished by molecular orbital calculations (AM1) by means of comparison. Additionally, the bond lengths of the compounds were analyzed in order to verify the occurance of electronic resonance. Bond lengths and bond angles in the pyrimidine ring and the benzylidene portion compare well with those found in similar compounds. 2-(N'-benzylidenehydrazino)-4-trifluoromethyl-pyrimidine, crystallized in the triclinic space group P-1 solvated with a molecule of water, while 2-(N'-2-methyl-benzylidenehydrazino)-5-methyl-4trifluoromethyl-pyrimidine crystallized in the tetragonal space group P41. The azomethine moieties showed a trans-planar conformation. The energy-minimized structures of both compounds are in good agreement with their X-ray crystal structures. Nevertheless, a significant difference between calculated and experimental data regarding to the ring planarity was observed due to relevant intermolecular interactions in the real structures. Finally, aromaticities of both pyrimidines and phenyl rings were determined using HOMA calculations.

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Preparation, molecular and crystal structures of 3-(1-amino-2,2,2-trifluoroethylidene)-1,1,4,5,6,7-hexafluoroindan-2-one, 2-amino-1,1,4,5,6,7-hexafluoro-3-trifluoroacetylindene, and their complexes with dioxane and pyridine

et al. 2008

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Supramolecular structure of 6-phenyl-2-chloropyrimidine-4-carboxamide and its complexes with dioxane and ethanol

Cited by 4 publications

References 11 publications

Hydrogen-bond coordination in organic crystal structures: statistics, predictions and applications

Hydrogen-bond coordination in organic crystal structures: statistics, predictions and applications

Crystal Structure, Aromatic Character and AM1 Calculations of 2-(N`- Benzylidenehydrazino)-4-trifluoromethyl-pyrimidine and 2-(N`-2-Methylbenzylidenehydrazino)- 5-methyl-4-trifluoromethyl-pyrimidine~!2010-02-08~!2010-05-04~!2010-06-22~!

Preparation, molecular and crystal structures of 3-(1-amino-2,2,2-trifluoroethylidene)-1,1,4,5,6,7-hexafluoroindan-2-one, 2-amino-1,1,4,5,6,7-hexafluoro-3-trifluoroacetylindene, and their complexes with dioxane and pyridine

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