Organic alloys of room temperature liquids thiophenol and selenophenol

Thomas, Sajesh P.; Ranganathan, S.; Row, Tayur N. Guru

doi:10.1039/c5cc03322e

Cited by 50 publications

(58 citation statements)

References 45 publications

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“…magnitude smaller than the corresponding value in the BCP associated with the S•••S contact in the S--S_lat(HT) interaction. It is worth mentioning that the computed values of the electronic density in the BCPs associated with the S•••S contacts of HT and the shorter S•••S contacts of LT are very similar to the experimental value determined for the S•••S contacts in TiS2 77 and the computed values for other organic crystals featuring S•••S chalcogen interactions 78,79. …”

supporting

confidence: 80%

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Francese

Mota

Deumal

et al. 2019

Crystal Growth & Design

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The spin transitions undergone by several molecular crystals of dithiazolyl (DTA) radicals make this type of radicals promising candidates for future sensors and memory devices. Here, we present a systematic computational study of the intermolecular interactions existing in the two polymorphs of the neutral radical 1,3,5-trithia-2,4,6-triazapentalenyl in order to elucidate the origin of the difference in energy between those two polymorphs involved in its spin transition and to understand the crystal packing of this prototype of bistable materials. The π-π interactions between radicals are the main driving force for the crystal packing of both polymorphs, which comprises π-stacks of radicals. Among the interstack interactions, the strongest ones are those mediated by six-and four-center S•••N bridges. The difference in energy between polymorphs, in turn, is mainly controlled also by the intrastack π-π intermolecular interactions, and the interstack S•••S contacts instead of the S•••N contacts. Since the supramolecular motifs herein identified as important for the crystal packing and/or for the energy difference between polymorphs (and, thus, for the spin transition temperature) are common to other members of the DTA family, our results provide valuable information to understand better the structure and properties of other switchable DTA-based materials.

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supporting

confidence: 80%

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Francese

Mota

Deumal

et al. 2019

Crystal Growth & Design

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“…The lattice parameters of C 6 H 6 Cl are very similar to (C 6 H 5 OH)Á0.5H 2 O and the principal difference on substitution of Br and I is an increase in the length of the a axis as the length of the carbon-halogen bond increases, these being roughly co-aligned with a in the same fashion as the C-O bond in phenol hemihydrate. Similarly, both thiophenol (JUJPEL; Thomas et al, 2015) and selenophenol (JUJPAH; Thomas et al, 2015) adopt the same packing as the phenol molecule in phenol hemihydrate. These are reported in space group Pnab rather than the conventional setting of Pbcn, otherwise the only meaningful difference is the presence of S-HÁ Á ÁS or Se-HÁ Á ÁSe chains long the crystal's a axis instead of rings of O-HÁ Á ÁO hydrogen bonds via H 2 O.…”

Section: Database Surveymentioning

confidence: 99%

Phenol hemihydrate: redetermination of the crystal structure by neutron powder diffraction, Hirshfeld surface analysis and characterization of the thermal expansion

Fortes

2020

Acta Cryst E

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Phenol hemihydrate, C5H5OH·0.5H2O, crystallizes in the space group Pbcn, Z = 8. The previously published crystal structure [CSD refcode PHOLHH; Meuthen & von Stackelberg (1960). Z. Elektrochem. 64, 387–390] is shown to be incorrect. Pairs of phenol molecules, related by an inversion centre, are bridged by one water molecule via O—H...O hydrogen bonds; an extended R 4 4(8) hydrogen-bonded motif links these inversion dimers into chains parallel to the c axis. Packing of the chains is achieved by weaker T-shaped C—H...π interactions between nearest neighbour phenol molecules in the bc plane. Analysis of the thermal expansion and parameterization with a Debye model in terms of the linear elastic moduli shows that the c axis is ∼3 times stiffer than the two orthogonal directions.

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“…Studies on H 2 S complexes in the gas phase suggest that the S-H donor behaves very similarly to O-H and N-H, irrespective of a large involvement of the dispersion interaction (Bhattacherjee et al, 2013;Bhattacharyya et al, 2013). Very few crystallographic studies have been reported in the literature (Steiner, 2000;Nangia & Desiraju, 1999;Thomas, Sathishkumar & Row, 2015) including a Cambridge Structural Database (CSD) analysis (Allen et al, 1997), which clearly establishes the significantly low number of examples for the occurrence of S-HÁ Á ÁS hydrogen bonds. Indeed, the current version of the CSD (Version 5.37, November 2015) has only 60 crystal structures which possess S-HÁ Á ÁS hydrogen bonds out of 160 organic molecules having S-H bonds.…”

Section: Introductionmentioning

confidence: 99%

Exploring the rare S—H...S hydrogen bond using charge density analysis in isomers of mercaptobenzoic acid

Pavan

Sarkar

Row

2017

Acta Crystallogr Sect B

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Experimental and theoretical charge density analyses on isomers of mercaptobenzoic acid have been carried out to quantify the hydrogen bonding of the hitherto less explored thiols, to assess the strength of the interactions using the topological features of the electron density. The electron density study offers interesting insights into the nature of the S-H...S interaction. The interaction energy is comparable with that of a weak hydrogen bond. The strength and directionality of the S-H...S hydrogen bond is demonstrated to be mainly due to the conformation locking potential of the intramolecular S...O chalcogen bond in 2-mercaptobenzoic acid and is stronger than in 3-mercaptobenzoic acid, which lacks the intramolecular S...O bond. The para-substituted mercaptobenzoic acid depicts a type I S...S interaction.

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Organic alloys of room temperature liquids thiophenol and selenophenol

Cited by 50 publications

References 45 publications

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Reorganization of Intermolecular Interactions in the Polymorphic Phase Transition of a Prototypical Dithiazolyl-Based Bistable Material

Phenol hemihydrate: redetermination of the crystal structure by neutron powder diffraction, Hirshfeld surface analysis and characterization of the thermal expansion

Exploring the rare S—H...S hydrogen bond using charge density analysis in isomers of mercaptobenzoic acid

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