The evaluation of the role of C–H⋯F hydrogen bonds in crystal altering the packing modes in the presence of strong hydrogen bond

Kaur, Gurpreet; Singh, Sandhya; Sreekumar, Amritha; Choudhury, Angshuman Roy

doi:10.1016/j.molstruc.2015.10.105

Cited by 25 publications

(18 citation statements)

References 67 publications

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“…Both polymorphs feature non-coplanar phenyl rings and a planar, thermochromic polymorph, β [77]. A fourth planar polymorph was also reported two years ago [78]. All the four polymorphs are in the enol form featuring an intramolecular O-H•••N H bond.…”

Section: Introductionmentioning

confidence: 82%

Mononuclear Lanthanide(III)-Salicylideneaniline Complexes: Synthetic, Structural, Spectroscopic, and Magnetic Studies

et al. 2018

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The reactions of hydrated lanthanide(III) [Ln(III)] nitrates and salicylideneaniline (salanH) have provided access to two families of mononuclear complexes depending on the reaction solvent used. In MeCN, the products are [Ln(NO3)3(salanH)2(H2O)]·MeCN, and, in MeOH, the products are [Ln(NO3)3(salanH)2(MeOH)]·(salanH). The complexes within each family are proven to be isomorphous. The structures of complexes [Ln(NO3)3(salanH)2(H2O)]·MeCN (Ln = Eu, 4·MeCN_Eu, Ln = Dy, 7·MeCN_Dy; Ln = Yb, 10·MeCN_Yb) and [Ln(NO3)3(salanH)2(MeOH)]·(salanH) (Ln = Tb, 17_Tb; Ln = Dy, 18_Dy) have been solved by single-crystal X-ray crystallography. In the five complexes, the LnIII center is bound to six oxygen atoms from the three bidentate chelating nitrato groups, two oxygen atoms from the two monodentate zwitterionic salanH ligands, and one oxygen atom from the coordinated H2O or MeOH group. The salanH ligands are mutually “cis” in 4·MeCN_Eu, 7·MeCN_Dy and 10·MeCN_Yb while they are “trans” in 17_Tb and 18_Dy. The lattice salanH molecule in 17_Tb and 18_Dy is also in its zwitterionic form with the acidic H atom being clearly located on the imine nitrogen atom. The coordination polyhedra defined by the nine oxygen donor atoms can be described as spherical tricapped trigonal prisms in 4·MeCN_Eu, 7·MeCN_Dy, and 10·MeCN_Yb and as spherical capped square antiprisms in 17_Tb and 18_Dy. Various intermolecular interactions build the crystal structures, which are completely different in the members of the two families. Solid-state IR data of the complexes are discussed in terms of their structural features. 1H NMR data for the diamagnetic Y(III) complexes provide strong evidence that the compounds decompose in DMSO by releasing the coordinated salanH ligands. The solid complexes emit green light upon excitation at 360 nm (room temperature) or 405 nm (room temperature). The emission is ligand-based. The solid Pr(III), Nd(III), Sm(III), Er(III), and Yb(III) complexes of both families exhibit LnIII-centered emission in the near-IR region of the electromagnetic spectrum, but there is probably no efficient salanH→LnIII energy transfer responsible for this emission. Detailed magnetic studies reveal that complexes 7·MeCN_Dy, 17_Tb and 18_Dy show field-induced slow magnetic relaxation while complex [Tb(NO3)3(salanH)2(H2O)]·MeCN (6·MeCN_Tb) does not display such properties. The values of the effective energy barrier for magnetization reversal are 13.1 cm−1 for 7·MeCN_Dy, 14.8 cm−1 for 17_Tb, and 31.0 cm−1 for 18_Dy. The enhanced/improved properties of 17_Tb and 18_Dy, compared to those of 6_Tb and 7_Dy, have been correlated with the different supramolecular structural features of the two families. The molecules [Ln(NO3)3(salanH)2(MeOH)] of complexes 17_Tb and 18_Dy are by far better isolated (allowing for better slow magnetic relaxation properties) than the molecules [Ln(NO3)3(salanH)2(H2O)] in 6·MeCN_Tb and 7·MeCN_Dy. The perspectives of the present initial studies in the Ln(III)/salanH chemistry are discussed.

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Section: Introductionmentioning

confidence: 82%

Mononuclear Lanthanide(III)-Salicylideneaniline Complexes: Synthetic, Structural, Spectroscopic, and Magnetic Studies

et al. 2018

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“…Furthermore, two crystal structures which are isostructural can also exhibit the behaviour of isomorphism (Esteves de Castro et al, 2007;Tykarska & Gdaniec, 2013) having a similar space groups with identical unit-cell parameters. Currently, the interchange between the substituents (such as Cl/CH 3 , H/F or H/CF 3 ) in a molecule is an interesting problem in crystal engineering (Dey & Chopra, 2017;Chopra & Row, 2008;Nayak et al, 2011Nayak et al, , 2012Kaur et al, 2012Kaur et al, , 2016Karanam & Choudhury, 2013;Gelbrich et al, 2012) and it is desirable to rationalize whether this chemical replacement can affect supramolecular assemblies in a significant manner (assuming differences in electronic and steric factors). This has implications for the observation of isostructurality for such compounds in solids.…”

Section: Introductionmentioning

confidence: 99%

Quantitative analysis of solid-state diversity in trifluoromethylated phenylhydrazones

Dey

Chopra

2017

Acta Crystallogr Sect B

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The cooperative roles of various structural motifs associated with the presence of different intermolecular interactions in the formation of molecular crystals are investigated in a series of trifluoromethylated phenylhydrazones. Out of the six compounds analysed, two exhibit three-dimensional structural similarities with geometrically equivalent building blocks, while a third exists as two polymorphic forms crystallized from ethanol solutions at low temperature (277 K) and room temperature (298 K), respectively. The compounds were characterized via single-crystal and powder X-ray diffraction techniques and differential scanning calorimetry. In the absence of any strong hydrogen bonding, the supramolecular constructs are primarily stabilized via molecular pairs with a high dispersion-energy contribution, due to the presence of molecular stacking along the molecular backbone along with C-H...π interactions in the solid state, in preference to an electrostatic contribution. The interaction energies for the most stabilizing molecular building blocks are in the range -29 to -43 kJ mol. In addition, weak N-H...F, C-H...F and N-H...C interactions and F...F, F...C, F...N and C...N contacts act as secondary motifs, providing additional stability to the crystal packing. The overall molecular arrangements are carefully analysed in terms of their nature and energetics, and the roles of different molecular pairs towards the crystal structure are delineated. A topological study using the quantum theory of atoms in molecules was used to characterize all the atomic interactions in the solid state. It established the presence of (3, -1) bond critical points and the closed-shell nature of all the interactions.

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“…The preparations of Schiff bases (2a-2d) were as reported in the literature [16,39]. Schiff bases were prepared by the condensation of 0.1 mol of the corresponding benzaldehyde and 0.1 mol of 4-aminophenol in ethanol for 3 h under reflux.…”

Section: Synthesis Of Schiff Bases (2a-2d)mentioning

confidence: 99%

“…Schiff base ligands (2a-2d) bearing four different side groups at the para position on the terminal phenyl ring were prepared from the condensation reaction of 4-aminophenol with benzaldehyde, p -fluoro-, chloro-, and bromobenzaldehyde in ethanol[16,39]. Full substituted cyclotriphosphazene products (3a-3d) were synthesized from the nucleophilic substitution reactions of chlorocyclotriphosphazene (1) with Schiff bases including hydroxyl groups in high yields.…”

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confidence: 99%

Synthesis of new cyclotriphosphazene derivatives bearing Schiff bases and their thermal and absorbance properties

et al. 2020

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In this study, a series of cyclotriphosphazene derivatives containing a Schiff base (3a-3d) were synthesized by the reactions of hexachlorocyclotriphosphazene (1) with bis-aryl Schiff bases (2a-2d) having different terminal groups (H, F, Cl, and Br). The products (3a-3d) were characterized by elemental and mass analyses, FT-IR, and 1 H, 13 C, and 31 P NMR spectroscopies. Furthermore, the structure of compound 3a was also determined by X-ray crystallography. The thermal behaviors and the spectral properties of the new cyclotriphosphazene compounds (3a-3d) were investigated and the results were compared in the series.

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The evaluation of the role of C–H⋯F hydrogen bonds in crystal altering the packing modes in the presence of strong hydrogen bond

Cited by 25 publications

References 67 publications

Mononuclear Lanthanide(III)-Salicylideneaniline Complexes: Synthetic, Structural, Spectroscopic, and Magnetic Studies

Mononuclear Lanthanide(III)-Salicylideneaniline Complexes: Synthetic, Structural, Spectroscopic, and Magnetic Studies

Quantitative analysis of solid-state diversity in trifluoromethylated phenylhydrazones

Synthesis of new cyclotriphosphazene derivatives bearing Schiff bases and their thermal and absorbance properties

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