A combined experimental and quantum chemical (DFT and AIM) study on molecular structure, spectroscopic properties, NBO and multiple interaction analysis in a novel ethyl 4-[2-(carbamoyl)hydrazinylidene]-3,5-dimethyl-1H-pyrrole-2-carboxylate and its dimer

Singh, R.N.; Kumar, Amit; Tiwari, Rohit; Rawat, Poonam; Gupta, Vikram

doi:10.1016/j.molstruc.2012.11.059

Cited by 86 publications

(32 citation statements)

References 53 publications

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“…Global reactivity descriptors as electronegativity (χ) = -1/2(ε LUMO + ε HOMO ), chemical potential (μ) = 1/2 (ε LUMO + ε HOMO ), global hardness (η) = 1/2 (ε LUMO -ε HOMO ), global softness (S) = 1/2η and electrophilicity index (ω) = μ 2 /2η are highly successful in predicting global reactivity trends [49][50][51][52][53][54][55][56][57][58][59][60][61]. According to Parr et …”

Section: Global Reactivity Descriptorsmentioning

confidence: 99%

“…For this purpose, appropriate local reactivity descriptors as Fukui function to describe the reactivity of an atom in a molecule are needed to be defined. The local reactivity descriptors [49][50][51][52][53][54][55][56][57][58][59][60][61] such as Fukui functions f k + (r), f k -(r) are calculated using the following equations as: are calculated using following equations as: s k Computational calculation as an alternate choice provides extensive properties of materials, eg. hyperpolarizability which is difficult task to measure directly [67].…”

Section: Local Reactivity Descriptorsmentioning

confidence: 99%

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Synthesis, conformational, spectroscopic and chemical reactivity analysis of 2-cyano-3-(1H-pyrrol-2-yl)acrylohydrazide using experimental and quantum chemical approaches

Rawat

Singh

2015

Journal of Molecular Structure

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Section: Global Reactivity Descriptorsmentioning

confidence: 99%

Section: Local Reactivity Descriptorsmentioning

confidence: 99%

Synthesis, conformational, spectroscopic and chemical reactivity analysis of 2-cyano-3-(1H-pyrrol-2-yl)acrylohydrazide using experimental and quantum chemical approaches

Rawat

Singh

2015

Journal of Molecular Structure

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“…AIM methodology has been applied to exclude or confirm the existence of intramolecular hydrogen bonds [102][103][104][105][106]. In an earlier study of the spectroscopic properties of pyrrole-2-carbaldehyde, the formation of intramolecular interactions C=O … H-N was proposed [30].…”

Section: Aim Studiesmentioning

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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“…1 below. The basis set superposition error (BSSE) [27] was taken into account using the counterpoise (CP) correction method when calculating the binding energy.…”

Section: Methodsmentioning

confidence: 99%

Utilization of theoretical studies of the imprinting ratio to guide experimental research into the molecular imprinted polymers formed using enrofloxacin and methacrylic acid

Liu

Zhang

et al. 2014

J Mol Model

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Computational approaches have been suggested as rational and fast methods for optimizing imprinting ratios. The B3LYP/6-31 g(d,p) level was applied to simulate the self-assembled system of molecularly imprinted polymers (MIPs) formed by enrofloxacin (ENRO) and methacrylic acid (MAA). Geometry optimization, the bonding situation, and the binding energies involved were studied to determine the impact of varying the imprinting ratio on the recognition characteristics. These theoretical results showed that the compound with an ENRO:MAA ratio of 1:7 had the lowest binding energy and the most stable structure. MIPs with different imprinting ratios of ENRO to MAA were then prepared in order to study the binding capacities of the polymers experimentally. The experimental and theoretically calculated results for these polymers were found to be consistent with each other. In dynamic adsorption experiments on the MIPs, the adsorption reaction was observed to reach a balanced state after 120 min. Analysis of the Scatchard plot revealed that the dissociation constant (K d) and the apparent maximum binding capacity (Q max) of MIPs with high-affinity sites were 451.67 mg/L and 42.23 mg/g, respectively, whereas the dissociation constant and apparent maximum binding capacity of MIPs with low-affinity sites were 883.39 mg/L and 73.15 mg/g, respectively. The quantity of ENRO adsorbed onto the MIPs was considerably higher than the quantities of ciprofloxacin (CIP) and ofloxacin (OFL) adsorbed, indicating that these MIPs have a much higher specific absorption capacity than the corresponding non-imprinted polymers.

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A combined experimental and quantum chemical (DFT and AIM) study on molecular structure, spectroscopic properties, NBO and multiple interaction analysis in a novel ethyl 4-[2-(carbamoyl)hydrazinylidene]-3,5-dimethyl-1H-pyrrole-2-carboxylate and its dimer

Cited by 86 publications

References 53 publications

Synthesis, conformational, spectroscopic and chemical reactivity analysis of 2-cyano-3-(1H-pyrrol-2-yl)acrylohydrazide using experimental and quantum chemical approaches

Synthesis, conformational, spectroscopic and chemical reactivity analysis of 2-cyano-3-(1H-pyrrol-2-yl)acrylohydrazide using experimental and quantum chemical approaches

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

Utilization of theoretical studies of the imprinting ratio to guide experimental research into the molecular imprinted polymers formed using enrofloxacin and methacrylic acid

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