Directing role of functional groups in selective generation of C–H⋯π interactions: In situ cryo-crystallographic studies on benzyl derivatives

Nayak, Susanta K.; Ranganathan, S.; Row, Tayur N. Guru

doi:10.1039/c001190h

Cited by 73 publications

(64 citation statements)

References 49 publications

(16 reference statements)

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“…These interactions are well within range for reported C-H··· interactions (2.3-3.4 Å). 29 These latter are also visible in the solid state packing motif for toluene, 33 which in addition to edge to face interactions (2.78 Å), exhibits closer C-H··· interactions from the methyl group (2.61 Å) ( Table 2). While no Sn-Br interactions were seen between neighbouring molecules, the closest distances being well over 8 Å, C-H···Br interactions were observed (3.03-3.10 Å) between chains.…”

Section: Aryltin Hydrides and Bromides (4 8)mentioning

confidence: 90%

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Stabilizing, non-covalent interactions in the solid state structure of novel aryltin hydrides and halogenides

et al. 2014

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A group of novel aryltin chlorides, bromides and hydrides (Ar n SnY 4-n ) 2, Y = Cl, Br, H) have been synthesized and structurally characterized via X-ray diffraction. These compounds display noncovalent intermolecular interactions in the form of edge to face, -stacking and C-H··· interactions resulting in discrete arrangements in the solid state. The strength of these interactions and their effect on resulting structural parameters, as well as the consequence of the aromatic substituent on the type of interactions present, will be highlighted and discussed. Résumé: De nouveaux chlorures, bromures et hydrures d'arylétain (Ar n SnY 4-n ) (où Ar = o-tolyl, 2,6-xylyl, 1-naphthyl, 2-naphthyl ou p-n-butylphenyl, et Y = Cl, Br ou H) ont été synthétisés et leur structure été déterminée par cristallographie aux rayons X. Ces composées présentent des interactions intermoléculaires non covalentes de type bord-face, empilement et C-H···, qui conduisent à des arrangements distincts à l'état solide. La force de ces interactions, leur effet sur les caractéristiques structurelles qui en résultent et l'impact du substituant aromatique sur les types d'interaction présents, seront exposés et étudiés. [Traduit par la Rédaction]Mots-clés : halogénure d'arylétain, hydrure d'arylétain, motifs d'un empilement cristallin, interactions intermoléculaires, empilement .

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Section: Aryltin Hydrides and Bromides (4 8)mentioning

confidence: 90%

“…The role of aromatic noncovalent interactions in the stabilization of compounds in solid state and their importance in chemical and biological processes have been well documented. [29][30][31][32][33] However, their presence and ultimately their effect on aryltin species have never been studied.…”

Section: Introductionmentioning

confidence: 99%

Stabilizing, non-covalent interactions in the solid state structure of novel aryltin hydrides and halogenides

et al. 2014

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“…4 was refined as a 2-component inversion twin (-100 0-10 00-1) using the TWIN option in SHELXL and refined with a BASF of 0.03. Electrostatic non-covalent inter-molecular interactions [19][20][21][22], van der Waals contacts (C-H···X) [23][24][25], and halide interactions (I···N, I···S, I···I) [26][27][28] were determined by the programs Mercury [29] and Diamond [30] using the centroids and planes and other features of these programs. All values for published compounds were based on a Cambridge Structural Database [31] search, and all values for presented and published compounds fall within expected ranges.…”

Section: Single-crystal Xrd Of 1 Andmentioning

confidence: 99%

Toward the synthesis of thiadiazole-based therapeutic agents: synthesis, spectroscopic study, X-ray analysis, and cross-coupling reactions of the key intermediate 3,5-diiodo-1,2,4-thiadiazole

2019

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The 1,2,4-thiadiazole moiety is an important component of several biologically active compounds, and varying substituents on this aromatic ring is one of the possible methods to develop novel thiadiazole-based drugs for medicine. A key building block to this end, namely 3,5-diiodo-1,2,4-thiadiazole (1), has been synthesized and characterized in this work for the first time. 1 has exhibited high selectivity for the replacement of iodine atom at position C5 (carbon next to sulfur) in Sonogashira-type cross-coupling reactions with phenylacetylene. Therefore, 3-iodo-5-(phenylethynyl)-1,2,4-thiadiazole (4) or 3,5-bis(phenylethynyl)-1,2,4-thiadiazole (5) could be synthesized selectively depending on reaction conditions. All three novel molecules have been characterized by NMR, IR, Raman, mass, and UV spectroscopies, and their solid phase structures have been determined by single-crystal X-ray diffraction. 1 is expected to be a key starting material for producing thiadiazole-based therapeutic agents using cross-coupling reactions.

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“…The packing mode is influenced by CH/π hydrogen bonds occurring between the benzene ring and sp 2 and sp 3 CHs, depending on the acidity of the benzyl proton [72].…”

Section: Crystal Packingmentioning

confidence: 99%

The CH/π Hydrogen Bond: Implication in Crystal Engineering

Nishio¹,

Umezawa

Suezawa

et al. 2012

The Importance of Pi‐Interactions in Crystal Engineering

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Directing role of functional groups in selective generation of C–H⋯π interactions: In situ cryo-crystallographic studies on benzyl derivatives

Cited by 73 publications

References 49 publications

Stabilizing, non-covalent interactions in the solid state structure of novel aryltin hydrides and halogenides

Stabilizing, non-covalent interactions in the solid state structure of novel aryltin hydrides and halogenides

Toward the synthesis of thiadiazole-based therapeutic agents: synthesis, spectroscopic study, X-ray analysis, and cross-coupling reactions of the key intermediate 3,5-diiodo-1,2,4-thiadiazole

The CH/π Hydrogen Bond: Implication in Crystal Engineering

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