Ethyl 5-formyl-3,4-dimethyl-1<i>H</i>-pyrrole-2-carboxylate

Wu, Wei-Na; Wang, Yuan; Wang, Qiufen

doi:10.1107/s160053680902323x

Cited by 5 publications

(4 citation statements)

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“…Cambridge Structural Database (CSD) searches on 2-acylpyrroles reveal that there are also some other instances of 2-acylpyrroles which form dimers in the solid phase by N-H … O=C interactions [109][110][111][112][113][114][115][116][117][118][119][120][121][122][123][124][125]. Table 3 Table 2: Geometrical, and topological parameters of X-H … O=C hydrogen bonds (in Å and degrees) with H-bond energies E HB in kcal mol -1 of 2-acylpyrrole dimers calculated at the B3LYP/6-311++G(d,p) level of theory; data calculated at B3LYP/6-311+G* are given in parentheses.…”

Section: O Hydrogen Bondsmentioning

confidence: 99%

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Dubis

2014

J Phys Chem Biophys

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2-carboxylic acids [3] and corresponding esters [4]. Pyrrole-2-carboxylates are also useful substrates for the preparation of more complex pyrrole containing systems [5] such as ketorolac, a drug with anti-inflammatory and analgesic properties [6]. It is noted that the 2-acylpyrrole motif is widespread in nature. There are many examples of 2-acylpyrrole based molecules (Figure 1) with various biological activities [7,8]. Representative examples are pyoluteorin and pyrrolomycin D, secondary metabolites produced by marine Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT StudiesAlina T Dubis* Institute of Chemistry, University of Białystok, Hurtowa 1, Poland AbstractConformations of alpha-substituted pyrroles have been effectively studied using spectroscopic methods assisted by theoretical calculations developed in the recent decade. The question of how to effectively study the conformation of 2-acylpyrrole no longer remains unanswered. The detailed spectroscopic studies conducted in the last decade and interpreted on the basis of theoretical calculations provide a satisfactory answer to that question. Based on the Density Functional Theory (DFT) calculations of conformational properties of 2-acylpyrroles, for which two stable rotameric forms were predicted, syn and anti-conformers have been studied either by experimental or theoretical methods. The family of 2-acylpyrroles have both a proton donor N-H group and a proton acceptor C=O group. This structure favors the formation of doubly hydrogen-bonded cyclic dimers connected by two N-H...O=C bonds. The tendency to form cyclic dimers stabilizes the syn-conformation. Due to these properties 2-acylpyrroles can be used as structural models for the conformational analysis of peptides.This review summarizes recent investigations of conformations of 2-acylpyrroles, with a particular emphasis on the hydrogen bonds forming within these systems. The influence of 2-substitution on different aspects of stability of these molecular systems and the usefulness of infrared spectroscopy supported by theoretical calculations in H-bonds and conformational studies are discussed. Among the molecular properties hydrogen bond energy, structural characteristics such as C=O bond length of dimers and unique spectral features of 2-acylpyrroles that can be used to predict and investigate the conformation and structure of proteins are considered.Graphical abstract. The potential energy diagram of 2-acylpyrroles as a function of the dihedral angle pyrrole ringcarbonyl group of bond rotation. Most stable conformer syn converts to conformer anti via the transition state TS1; less stable conformer anti converts to conformer syn via the transition state TS2. conformational research and can greatly support experimental work with quite good accuracy. Among the most useful parameters are geometrical parameters, relative conformational energies, barriers to internal rotation and vibrational frequencies for each conformer. Journal of Physical Chemistry & BiophysicsEnergy differ...

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Section: O Hydrogen Bondsmentioning

confidence: 99%

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Dubis

2014

J Phys Chem Biophys

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“…For the antioxidant and DNA-binding properties of hydrazone complexes, see: Liu & Yang (2009). For the synthesis and structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see: Wu et al (2009). For the similar structure of ethyl 5-[(3,4dimethyl-1H-pyrrole-2-carboxylimino)-methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate monohydrate, see: Wang et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

“…Isonicotinohydrazide (0.137 g, 1 mmol) and ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate (0.167 g, 1 mmol) (Wu et al, 2009) was dissolved in an ethanol solution. The mixture was stirred for 4 h at room temperture.…”

Section: S2 Experimentalmentioning

confidence: 99%

Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}-3,4-dimethyl-1H-pyrrole-2-carboxylate dihydrate

Zhang¹,

Wang²,

Lu³

et al. 2011

Acta Cryst E

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In the title compound, C16H18N4O3·2H2O, the dihedral angle between the pyrrole and pyridine rings in the hydrazone molecule is 7.12 (3)°. In the crystal structure, intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds link the hydrazone and water molecules into double layers parallel to (101). The crystal packing exhibits weak π–π interactions between the pyrrole and pyridine rings of neighbouring hydrazone molecules [centroid–centroid distance = 3.777 (3) Å]. The crystal studied was a non-merohedral twin, the refined ratio of twin domains being 0.73 (3):0.27 (3).

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“…For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2carboxylate, see Wu et al (2009). For the similar structure of ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)iminomethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate, see Wang et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 3,4-dimethyl-5-[(E)-(phenylimino)methyl]-1H-pyrrole-2-carboxylate

Yang

et al. 2010

Acta Cryst E

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In the title compound, C16H18N2O2, the molecule adopts an E conformation about the C=N double bond. The dihedral angle between the pyrrole and phenyl rings is 41.55 (8)°. In the crystal structure, pairs of intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. In the dimer, the two pyrrole rings are almost coplanar and the two phenyl rings are parallel to each other.

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Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate

Cited by 5 publications

References 4 publications

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Conformational Preferences of 2-Acylpyrroles in Light of FT-IR and DFT Studies

Ethyl 5-{[(E)-2-(isonicotinoyl)hydrazinylidene]methyl}-3,4-dimethyl-1H-pyrrole-2-carboxylate dihydrate

Ethyl 3,4-dimethyl-5-[(E)-(phenylimino)methyl]-1H-pyrrole-2-carboxylate

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