An organometallic complex revealing an unexpected, reversible, temperature induced SC–SC transformation

Taylor, Rupert G. D.; Yeo, Benjamin Roy; Hallett, A. J. Hughes; Kariuki, Benson M.; Pope, Simon J. A.

doi:10.1039/c4ce00070f

Cited by 4 publications

(10 citation statements)

References 50 publications

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“…In doing so, series of tetrameric units are generated in the NmmCl crystal structure and with C–H···π(arene) interactions generate ruffled sheets. In contrast, NmoCl is isomorphous with NmoBr ( 84 ) ( TICDOZ01 ) 49 with N–H···O=C intermolecular interactions along the b -axis direction and short intramolecular interactions between the ortho -Cl12 and the N–H group. In addition, there are Cl12···C14 contacts between the ortho -Cl12 and symmetry related chlorinated aromatic rings.…”

Section: Resultsmentioning

confidence: 99%

“…Isomorphous relationships between structures in the 3 × 3 isomer grids show an overlap between five NxxCl isomers and their NxxBr analogues (as the NpmCl / Br , NpoCl / Br , NmoCl / Br , 84 NopCl 85 / Br , and NooCl / Br pairs). This correlates well with what has been noted with five of the Clxx / Brxx amide-bridge reversed analogues (see Table 3 ).…”

Section: Resultsmentioning

confidence: 99%

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Probing the Electronic Properties and Interaction Landscapes in a Series of N-(Chlorophenyl)pyridinecarboxamides

Gallagher

Hehir

Mocilac

et al. 2022

Crystal Growth & Design

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A 3 × 3 isomer grid of nine N -(chlorophenyl)pyridinecarboxamides ( NxxCl ) is reported with physicochemical studies and single crystal structures ( Nx = pyridinoyl moiety; xCl = aminochlorobenzene ring; x = para -/ meta -/ ortho -), as synthesized by the reaction of the substituted p -/ m -/ o -pyridinecarbonyl chlorides ( Nx ) with p -/ m -/ o -aminochlorobenzenes ( xCl ). Several of the nine NxxCl crystal structures display structural similarities with their halogenated NxxX and methylated NxxM relatives ( x = p -/ m- / o -substitutions; X = F, Br; M = methyl). Indeed, five of the nine NxxCl crystal structures are isomorphous with their NxxBr analogues as the NpmCl / Br , NpoCl / Br , NmoCl / NmoBr , NopCl / Br , and NooCl / Br pairs. In the NxxCl series, the favored hydrogen bonding mode is aggregation by N–H···N pyridine interactions, though amide···amide intermolecular interactions are noted in NpoCl and NmoCl . For the NoxCl triad, intramolecular N–H···N pyridine interactions influence molecular planarity, whereas NppCl·H 2 O (as a monohydrate) exhibits O–H···O, N–H···O1W, and O1W-H···N interactions as the primary hydrogen bonding. Analysis of chlorine-containing compounds on the CSD is noted for comparisons. The interaction environments are probed using Hirshfeld surface analysis and contact enrichment studies. The melting temperatures ( T m ) depend on both the lattice energy and molecular symmetry (Carnelley’s rule), and the melting points can be well predicted from a linear regression of the two variables. The relationships of the T m values with the total energy, the electrostatic component, and the strongest hydrogen bond components have been analyzed.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Probing the Electronic Properties and Interaction Landscapes in a Series of N-(Chlorophenyl)pyridinecarboxamides

Gallagher

Hehir

Mocilac

et al. 2022

Crystal Growth & Design

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“…A previous study reported (Ahn et al, 2001) that the polymorph of 3-BrCA undergoes a polymorphic transformation to the polymorph on heating above 373 K. In the present article, we investigate the possibility that a phase transformation may also occur for the polymorph of 3-ClCA. Polymorphic phase transformations (Taylor et al, 2014;Khoj et al, 2013;Yates & Sparkes, 2013;Palmer et al, 2012;Pete et al, 2015;Rubin-Preminger et al, 2004;Sørensen & Simonsen, 1989;Das et al, 2010;Hu & Englert, 2005;Zhang et al, 2005;Ahn et al, 2006;Williams et al, 2012) represent a 'tipping point' at which a gradual change in conditions (e.g. temperature) leads to the sudden conversion of one crystalline material into another (Dunitz, 1991;Meijer et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Polymorphic phase transformations of 3-chloro-trans-cinnamic acid and its solid solution with 3-bromo-trans-cinnamic acid

et al. 2018

Self Cite

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We have investigated the polymorphic phase transformations above ambient temperature for 3-chloro-trans-cinnamic acid (3-ClCA, CHClO) and a solid solution of 3-ClCA and 3-bromo-trans-cinnamic acid (3-BrCA, CHBrO). At 413 K, the γ polymorph of 3-ClCA transforms to the β polymorph. Interestingly, the structure of the β polymorph of 3-ClCA obtained in this transformation is different from the structure of the β polymorph of 3-BrCA obtained in the corresponding polymorphic transformation from the γ polymorph of 3-BrCA, even though the γ polymorphs of 3-ClCA and 3-BrCA are isostructural. We also report a high-temperature phase transformation from a γ-type structure to a β-type structure for a solid solution of 3-ClCA and 3-BrCA (with a molar ratio close to 1:1). The γ polymorph of the solid solution is isostructural with the γ polymorphs of pure 3-ClCA and pure 3-BrCA, while the β-type structure produced in the phase transformation is structurally similar to the β polymorph of pure 3-BrCA.

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“…Enantiotropic behavior has been observed unsurprisingly between forms with very similar unit cell parameters [31,32], but transformation more commonly involves larger shifts in the parameters [33][34][35]. Polymorphism and polymorphic phase transformations are difficult to predict and are often discovered fortuitously [26].…”

Section: Introductionmentioning

confidence: 99%

“…Polymorphic phase transformation is an area of continued research interest [26][27][28][29][30][31][32][33][34][35]. The transformation process is an indication of the fine balance in the interactions within the crystal that can be tipped by a relatively small change in conditions [36,37].…”

Section: Introductionmentioning

confidence: 99%

A Reversible Single-Crystal to Single-Crystal Thermal Phase Transformation of 3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethyl urea

Kariuki

El‐Hiti

2017

Crystals

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3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethylurea was synthesized and structurally characterized at 296 K, 200 K and 140 K. A reversible thermal phase transformation was observed at~170-180 K. On cooling, the structure transforms from a monoclinic to a triclinic crystal system. The isopropyl group is disordered above the phase transition temperature but is ordered below the transition temperature.

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An organometallic complex revealing an unexpected, reversible, temperature induced SC–SC transformation

Cited by 4 publications

References 50 publications

Probing the Electronic Properties and Interaction Landscapes in a Series of N-(Chlorophenyl)pyridinecarboxamides

Probing the Electronic Properties and Interaction Landscapes in a Series of N-(Chlorophenyl)pyridinecarboxamides

Polymorphic phase transformations of 3-chloro-trans-cinnamic acid and its solid solution with 3-bromo-trans-cinnamic acid

A Reversible Single-Crystal to Single-Crystal Thermal Phase Transformation of 3-(2-Bromo-4-(1-methylethyl)phenyl)-1,1-dimethyl urea

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