Inter- and intramolecular hydrogen bonds – Structures of 1-methylpyrrole-2-carboxamide and 1-hydroxypyrrole-2-carboxamide

Grabowski, Sławomir J.; Palusiak, Marcin; Dubis, Alina T.; Pfitzner, Arno; Zabel, Manfred

doi:10.1016/j.molstruc.2007.03.053

Cited by 11 publications

(5 citation statements)

References 39 publications

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“…We did not find any charge transfer energy ( E (2) ) for the C–H···O, C–H···C–H, C–H···H‐C (dihydrogen bonding) intramolecular interactions observed in the conjugate bases of O‐Glc by AIM analysis. This is in line with the finding of Grabowski, [ 90 ] who stated the intramolecular C–H···O and C–H···N interactions are hardly classified as H‐bonds.…”

Section: Resultssupporting

confidence: 92%

Computational insight into networking H‐bonds in open and cyclic forms of glucose

Kotena

Fattahi

2021

J of Physical Organic Chem

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We have studied the intramolecular H‐bonds existing in cyclic and open forms of glucose using B3LYP/6‐311++G(d,p) level, AIM, and NBO methods. The theoretical results indicated that based on acidity values, (ΔHacid), glucose in the open form is more acidic than cyclic form. The acidity values for open and cyclic glucose (332 and 338 kcal/mol) exhibit significantly lower values (i.e., stronger acid) than the reported acidity values for α‐/ß‐anomers of D‐glucopyranose and simple alcohols. Because their conjugate bases are more stabilized through trifurcated and bifurcated intramolecular H‐bonds. AIM analysis showed normal H‐bonds in the conjugate bases of open glucose (O‐Glc), bifurcated, and normal H‐bonds in the conjugate base of cyclic glucose. In the conjugate base of glucose, the O–H···O bonds are categorized as mostly electrostatic and strong, whereas multiple interactions including C–H···O, C–H···H–C (dihydrogen bonding), C–H···C–H, and C=O···H are categorized as weak H‐bonds. The NBO results confirm that the O–H···O intramolecular H‐bonds should be the strongest among all H‐bonds existing within glucose.

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Section: Resultssupporting

confidence: 92%

Computational insight into networking H‐bonds in open and cyclic forms of glucose

Kotena

Fattahi

2021

J of Physical Organic Chem

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“…The intermolecular HB interaction between two molecules of pyrrole‐2‐carbaldehyde derivatives has been studied by means of spectroscopic, diffraction, and theoretical methods including the Bader theory of atoms in molecules [2‐5] . The calculated HB energy for these dimers is comparable with the HB energy found for many typical acid dimers .…”

Section: Introductionmentioning

confidence: 78%

Can 2‐acylpyrroles form an intramolecular hydrogen bond?

Dubis

Stasiewicz

Pogorzelec‐Glaser

et al. 2015

J of Physical Organic Chem

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The formation of intramolecular hydrogen bonding by certain N-substituted 2-acylpyrroles has been demonstrated by B3LYP/aug-cc-pVDZ calculations, the quantum theory of atoms in molecules, and the natural bond orbital method. Total electron energy densities H BCP at the bond critical point of the H⋯O bond were applied to analyze the strength of these interactions. The relations between quantum theory of atoms in molecules, carbonyl stretching vibrational modes ν C = O , and natural bond orbital parameters associated with the formation of the C-H⋯O interaction have been established. The short contacts were found experimentally in the crystal structure of a new 2-acylpyrrole derivative 5-chloro-2-oxopentyl-1-(5-chloro-2-oxopentyl)pyrrolo-2-carboxylate. The influence of 2-and N-substitution of 2-acylpyrroles on C-H⋯O interaction energy is discussed. It was found that the methylene group may act as a proton donor leading to a red-shift or blue-shift phenomenon of the ν C-H stretching mode.

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“…Most of these data concern the analysis of intermolecular H-bonds in 2-acylpyrroles. Valuable information from diffraction analysis of 2-acylpyrroles was reported by Grabowski and co-workers [68,70,83,88] …”

Section: O=c Hydrogen Bonds the Intermolecular C=omentioning

confidence: 93%

“…There are also correlations between C=O bond length and Laplacian of the electron density at the BCP and total, kinetic and potential electron energy densities at this BCP (HC, GC and VC) 1-methylpyrrole-2-carboxamide (27) [88].…”

Section: Aim Studiesmentioning

confidence: 96%

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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Inter- and intramolecular hydrogen bonds – Structures of 1-methylpyrrole-2-carboxamide and 1-hydroxypyrrole-2-carboxamide

Cited by 11 publications

References 39 publications

Computational insight into networking H‐bonds in open and cyclic forms of glucose

Computational insight into networking H‐bonds in open and cyclic forms of glucose

Can 2‐acylpyrroles form an intramolecular hydrogen bond?

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

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