Structural versatility in hydrated rare earth(iii) 1,2-benzenedisulfonates

Deacon, Glen B.; Harika, Rita; Junk, Peter Courtney; Skelton, Brian W.; White, Allan H.

doi:10.1039/b614681c

Cited by 23 publications

(7 citation statements)

References 32 publications

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“…The total number of reliable structures of cations with overall composition H 7 O 3 + is 11 [CBZSUL01 (Roziere & Williams, 1978), GIDZEZ (Deacon, et al, 2007), HAZCAN (Jin et al, 2005), JOTQOY03 (Calleja et al, 2001), NITRAN01 (Andersen & Andersen, 1975), ODEBOO (Herzog et al, 2001), SALSUL (Mootz & Fayos, 1970), SINNAF (Ganin et al, 2006), SLBZAC10 (Attig & Mootz, 1976) A view of the asymmetric unit of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level for non-H atoms.…”

Section: Tablementioning

confidence: 99%

Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

2015

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The name `bath salts', for an emerging class of synthetic cathinones, is derived from an attempt to evade prosecution and law enforcement. These are truly illicit drugs that have psychoactive CNS (central nervous system) stimulant effects and they have seen a rise in abuse as recreational drugs in the last few years since first having been seen in Japan in 2006. The ease of synthesis and modification of specific functional groups of the parent cathinone make these drugs particularly difficult to regulate. MDPV (3,4-methylenedioxypyrovalerone) is commonly encountered as its hydrochloride salt (C16H21NO3·HCl), in either the hydrated or the anhydrous forms. This `bath salt' has various names in the US, e.g. `Super Coke', `Cloud Nine', and `Ivory Wave', to name just a few. We report here the structures of two forms of the HCl salt, one as a mixed bromide/chloride salt, C16H22NO3(+)·0.343Br(-)·0.657Cl(-) [systematic name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-ium-1-yl)pentan-1-one bromide/chloride (0.343/0.657)], and the other with the H7O3(+) cation, as well as the HCl counter-ion [systematic name: hydroxonium 1-(benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-ium-1-yl)pentan-1-one dichloride, H7O3(+)·C16H22NO3(+)·2Cl(-)]. This is one of a very few structures (11 to be exact) in which we have a new example of a precisely determined hydroxonium cation. During the course of researching the clandestine manufacture of MDPV, we were surprised by the fact that a common precursor of this illicit stimulant is known to be the fragrant species piperonal, which is present in the fragrances of orchids, most particularly in the case of the vanilla orchid. We found that MDPV can be made by a Grignard reaction of this heliotropin. This may also explain the unexpected appearance of the bromide counter-ion in some of the salts we encountered (C16H21NO3·HBr), one of which is presented here [systematic name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-ium-1-yl)pentan-1-one bromide, C16H22NO3(+)·Br(-)]. Complexation of MDPV with a forensic crystallizing reagent, HAuCl4, yields the tetrachloridoaurate salt of this drug, (C16H22NO3)[AuCl4]. The heavy-metal complexing agent HAuCl4 has been used for over a century to identify common quarternary nitrogen-containing drugs via microscopic identification. Another street drug, called ethylone (3,4-methylenedioxyethylcathinone), is regularly sold and abused as its hydrochloride salt (C12H15NO3·HCl), and its structure is herein described (systematic name: N-{1-[(benzo[d][1,3]dioxol-5-yl)carbonyl]ethyl}ethanaminium chloride, C12H16NO3(+)·Cl(-)). Marketed and sold as a `bath salt', `plant feeder', or `cleaning product', this drug is nothing more than a slight chemical modification of the banned drug methylone (3,4-methylenedioxymethcathinone). As with previously popular synthetic cathinones, the abuse of ethylone has seen a recent increase due to regulatory efforts on previous generations of cathinones that are now banned.

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Section: Tablementioning

confidence: 99%

Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

2015

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“…The indexing and refinement of the powder XRD pattern using the Louer's algorithm implemented in the STOE WinXPOW [45] program results in a monoclinic unit cell with the lattice parameters a = 2162.35 (14) pm, b = 875.27(7) pm, c = 1282.68(7) pm, β = 113.445(5)°(the results of the refinement in Table S7). The composition of 3 was determined with the combined interpretation of thermogravimetric (TG), CHNS and Energy Dispersive X-ray (EDX) analyses data.…”

Section: Characterization Of Compoundmentioning

confidence: 99%

“…[6,7] On the other hand, sulfonate (R-SO 3 -) and phosphonate (R-PO 3 2-) based compounds have been less intensively investigated. [8][9][10][11][12][13][14] This could be due to the more flexible coordination modes as well as the larger number of coordinating atoms which restricts structural diversity compared to the -CO 2 -counterpart. Thus, for phosphonate-based compounds mostly more dense layered materials are formed.…”

Section: Introductionmentioning

confidence: 97%

Systematic Hydrothermal Investigation of Metal Phosphonatobenzenesulfonates by High‐Throughput Methods

2010

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A high-throughput (HT) investigation using the rigid bifunctional ligand 4-phosphonobenzenesulfonic acid, H 2 O 3 P-C 6 H 4 -SO 3 H (H 3 L), generated five new phosphonatobenzenesulfonates with copper(II) or lead(II) ions. A comprehensive HT study comprising the screenings of different metal ions, metal salt types and the synthesis optimization were conducted whereby the influence of pH and molar ratios M 2+

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“…4a) is formulated as a central hydronium ion donating via CAHB to two acceptor water molecules. This form is found in six structures [CBZSUL01 (Roziere & Williams, 1978;neutron), GIDZEZ (Deacon et al, 2007), HAZCAN (Zhi-Min Jin et al, 2005), SALSUL (Mootz & Fayos, 1970), SOJZOH (Stoyanov et al, 2008) and XUMQIF (Czado & Mü ller, 2002)], with average dimensions OÁ Á ÁO = 2.47 (4) Å and = 0.50 (10). Isomer 2 of H 7 O 3 + (Fig.…”

Section: Two Isomers Of H 7 O 3 +mentioning

confidence: 99%

Molecular and supramolecular ionic aggregates H_xO_y^zin organic and organometallic crystalline hydrates

Bernal

Watkins

2014

Acta Crystallogr C

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Ionic aggregates of the form H(x)O(y)(z) (z ≠ 0) have been characterized during an analysis of 245 crystal structures extracted from the Cambridge Structural Database [Allen (2002). Acta Cryst. B58, 380-388]. A systematic nomenclature is proposed for these species. Three modes of hydrogen bonding are described, characterized in part by the distance between contiguous O atoms: normal (NHB; O···O = 2.6-3.0 Å), charge assisted (CAHB; O···O = 2.5 Å) and molecular (MHB; O···O = 2.4 Å). The three modes are consistent with previous reports, our experimental results, and quantum-chemical-optimized geometries and energetics. No evidence is presented concerning the possible existence or stability of these aggregates in solution. Rather, emphasis is placed on the necessity in crystal structure analysis to develop thoroughly existing hydrogen-bonded networks, ignorance of which can lead to erroneous crystal structure models and other physico-chemical data associated with composition and charge balance.

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Structural versatility in hydrated rare earth(iii) 1,2-benzenedisulfonates

Cited by 23 publications

References 32 publications

Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

Systematic Hydrothermal Investigation of Metal Phosphonatobenzenesulfonates by High‐Throughput Methods

Molecular and supramolecular ionic aggregates H_xO_y^zin organic and organometallic crystalline hydrates

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Structural versatility in hydrated rare earth(iii) 1,2-benzenedisulfonates

Cited by 23 publications

References 32 publications

Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

Crystallographic investigations of select cathinones: emerging illicit street drugs known as `bath salts'

Systematic Hydrothermal Investigation of Metal Phosphonatobenzenesulfonates by High‐Throughput Methods

Molecular and supramolecular ionic aggregates HxOyzin organic and organometallic crystalline hydrates

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Molecular and supramolecular ionic aggregates H_xO_y^zin organic and organometallic crystalline hydrates