Role of intermolecular interactions involving organic fluorine in trifluoromethylated benzanilides

Panini, Piyush; Chopra, Deepak

doi:10.1039/c2ce06254b

Cited by 58 publications

(44 citation statements)

References 78 publications

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“…As discussed previously on several occasions, fluorine‐centered non‐covalent interactions can be weak and directional . This is likely to arise from a universal intermolecular dispersion, either reinforced or opposed by a Columbic force.…”

Section: Introductionmentioning

confidence: 81%

Revealing Factors Influencing the Fluorine‐Centered Non‐Covalent Interactions in Some Fluorine‐Substituted Molecular Complexes: Insights from First‐Principles Studies

2018

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We examine the equilibrium structure and properties of six fully or partially fluorinated hydrocarbons and several of their binary complexes using computational methods. In the monomers, the electrostatic surface of the fluorine is predicted to be either entirely negative or weakly positive. However, its lateral sites are always negative. This enables the fluorine to display an anisotropic distribution of charge density on its electrostatic surface. While this is the electrostatic surface scenario of the fluorine atom, its negative sites in some of these monomers are shown to have the potential to engage in attractive engagements with the negative site(s) on the same atom in another molecule of the same type, or a molecule of a different type, to form bimolecular complexes. This is revealed by analyzing the results of current state-of-the-art computational approaches such as DFT, together with those obtained from the quantum theory of atoms in molecules, molecular electrostatic surface potential and symmetry adapted perturbation theories. We demonstrate that the intermolecular interaction energy arising in part from the universal London dispersion, which has been underappreciated for decades, is an essential factor in explaining the attraction between the negative sites, although energy arising from polarization strengthens the extent of the intermolecular interactions in these complexes.

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Section: Introductionmentioning

confidence: 81%

Revealing Factors Influencing the Fluorine‐Centered Non‐Covalent Interactions in Some Fluorine‐Substituted Molecular Complexes: Insights from First‐Principles Studies

2018

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“…The importance of such C-H···F interactions being weak and cooperative in nature has been realized in the crystal structure analysis of fluorinated N-(2-Chloropyridin-4-yl)-N′-phenylureas ( Fig. 2.11) [87], halogenated benzanilides (fluorinated [88] and hetero halogenated with at least one side of the phenyl ring contains fluorine [88][89][90]), trifluoromethyl (-CF 3 ) substituted benzanilides [91], fluoro-N-(pyridyl)benzamides [92], fluorine-substituted benzimidazoles [93]. In the crystal packing of a series of fluorinated N-(2-Chloropyridin-4-yl)-N′-phenylureas (Fig.…”

Section: Why Fluorine Is So Special?mentioning

confidence: 99%

“…For this purpose, 15 compounds were synthesized [10 crystal structures [91] [88,89] were determined] (Fig. 2.13a).…”

Section: Why Fluorine Is So Special?mentioning

confidence: 99%

Understanding of Noncovalent Interactions Involving Organic Fluorine

Panini¹,

Chopra²

2015

Lecture Notes in Chemistry

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Due to the unpredictable nature of organic fluorine in its participation in the formation of different supramolecular motifs which concomitantly influences the physicochemical properties of the compounds of interest, the study of noncovalent interactions involving organic fluorine will always be an expanding area of research amongst the scientific community. The participation of organic fluorine in the formation of intermolecular interactions has always been questioned. In this book chapter, we provide insights into new structural features, nature, and energetics associated with intermolecular interactions, namely C-H···F-C, C-F···F-C, C-F···X (N, O, S, halogen) from researchers across the world. The studies show that interactions involving fluorine are ubiquitous and play a central role in the existence of diversified solid state properties, namely polymorphism, crystal engineering, and cocrystallization.

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“…In the presence of a strong acceptor and donor atom, the crystal packing will be predominantly controlled by the presence of strong hydrogen bonds such as O/N-H· · · O/N. 4 In the past decade, the focus has shifted from strong intermolecular interactions to weak intermolecular interactions such as C-H· · · O/N, [5][6][7][8] C-H· · · X (X = -F, -Cl, -Br, -I), [9][10][11][12][13][14] C-H· · · π 15 and π · · · π 16,17 and lp · · · π 18,19 interactions present in the crystal structures. Weak * For correspondence intermolecular interactions involving organic fluorine have received special attention due to its small size, electronegativity and lipophilic character.…”

Section: Introductionmentioning

confidence: 99%

Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol

Panini

Shukla

Mohan³

et al. 2014

J Chem Sci

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In the present study, we have prepared and structurally characterized a derivative of 1,2,4 triazoles, namely 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol (T-1) via single crystal X-ray diffraction. The crystal structure was observed to be stabilized by the presence of various intermolecular interactions in the crystalline solid such as O-H· · · S, C-H· · · F, C-H· · · S, C-H· · · N, C-H· · · O, C-H· · · π, lp · · · π and π · · · π intermolecular interactions. The interaction energy of these interactions was evaluated through PIXEL method with decomposition of the total energy into the coulombic, polarization, dispersion and repulsion contribution. The study of the nature of H-bonds with sulfur reveals that stabilization due to contribution from polarization plays a significant role. It is noteworthy that the presence of the solvent molecules in the crystal structure were observed to provide stabilization to an otherwise destabilized molecular pair (comprising of two molecules of 1,2,4 triazoles in the asymmetric unit).

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Role of intermolecular interactions involving organic fluorine in trifluoromethylated benzanilides

Cited by 58 publications

References 78 publications

Revealing Factors Influencing the Fluorine‐Centered Non‐Covalent Interactions in Some Fluorine‐Substituted Molecular Complexes: Insights from First‐Principles Studies

Revealing Factors Influencing the Fluorine‐Centered Non‐Covalent Interactions in Some Fluorine‐Substituted Molecular Complexes: Insights from First‐Principles Studies

Understanding of Noncovalent Interactions Involving Organic Fluorine

Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol

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