Hydrogen Bonding Networks in Bis(amine)gold(I) Complexes with Disulfonylamide Anions

Ahrens, Birte; Friedrichs, Steffi; Herbst‐Irmer, Regine; Jones, Peter G.

doi:10.1002/1099-0682(200009)2000:9<2017::aid-ejic2017>3.0.co;2-0

Cited by 31 publications

(4 citation statements)

References 30 publications

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“…For the piperidine structures, one unexpected feature (that we failed to draw attention to at the time of the original publications) was a marked tendency for the gold moiety to lie axially with respect to the piperidine rings. Thus for [Au(pip)(SCN)] (refcode DIXBAQ; Strey et al, 2018), [Au(pip) 2 ][AgCl 2 ] (DUHQUS/DUQHUS01; Ahrens et al, 2000, corrected in Ahrens et al, 2003, [Au(CN)(pip)] (FIMSOL; Do ¨ring & Jones, 2013) and [Au(pip) 2 ]Cl (GOGFEN/GOGFEN01; Ahrens et al, 1999), all the absolute C-C-N-Au torsion angles lie in the range 65-72 � . A possible explanation might be that the low coordination number of gold alleviates the steric disadvantages somewhat.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of five halido gold complexes involving piperidine or pyrrolidine as ligands or (protonated) as cations

Döring,

Jones

2023

Acta Crystallogr E Cryst Commun

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In bromido(pyrrolidine-κN)gold(I) bis(pyrrolidine-κN)gold(I) bromide, [AuBr(pyr)]·[Au(pyr)2]Br (pyr = pyrrolidine, C4H9N), 2, alternating [AuBr(pyr)] molecules and [Au(pyr)2]+ cations are connected by aurophilic contacts to form infinite chains of residues parallel to the b axis. The chains are cross-linked by three N—H...Br− hydrogen bonds and an Au...Br contact to form a layer structure parallel to the ab plane. Trichlorido(piperidine-κN)gold(III), [AuCl3(pip)] (pip = piperidine, C5H11N), 3, consists of molecules with the expected square-planar coordination at the gold atom, which are connected by an N—H...Cl hydrogen bond and an Au...Cl contact to form a layer structure parallel to the ac plane. The structures of bis(piperidinium) tetrachloridoaurate(III) chloride, (pipH)2[AuCl4]Cl, 4, and bis(pyrrolidinium) tetrabromidoaurate(III) bromide, (pyrH)2[AuBr4]Br, 6, are closely related but not isotypic. Compound 6 crystallizes in space group Ibam; the Au and two Br atoms of the anion lie in the mirror plane x, y, 0, whereas the bromide ions occupy special positions 0, 0.5, 0 and 0, 0.5, 0.25, with site symmetry 2/m. The NH2 group forms a hydrogen bond to one bromide ion, and also a three-centre hydrogen bond to the other bromide atom and to a metal-bonded Br atom. The packing involves chains of hydrogen-bonded pyrrolidinium and bromide ions parallel to the c axis, combined with a layer structure of [AuBr4]− and bromide anions, parallel to the ab plane and involving Au...Br and Br...Br contacts. Compound 4, however, crystallizes pseudosymmetrically in space group Iba2; two chlorine atoms of the anion lie on the twofold axis 0.5, 0.5, z, and there are two independent cations. The packing is closely similar to that of 6, but there are no N—H...Cl hydrogen bonds to metal-bonded chlorines. The contact distances Au...Cl are appreciably longer than their Au...Br counterparts in 6, whereas the Cl...Cl contact is much shorter than Br...Br in 6. Tribromido(piperidine-κN)gold(III) crystallizes as its dichloromethane solvate, [AuBr3(pip)]·CH2Cl2, 7. It too displays a square-planar coordination at the gold atom. The packing involves hydrogen bonds N—H...Br, stacking of neighbouring AuBr3 units by Au...Br contacts, and a short Br...Br contact; these combine to form a layer structure parallel to the ac plane.

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Section: Database Surveymentioning

confidence: 99%

Crystal structures of five halido gold complexes involving piperidine or pyrrolidine as ligands or (protonated) as cations

Döring,

Jones

2023

Acta Crystallogr E Cryst Commun

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“…Only four other complexes of gold with morpholine are present in the CSD. Two of these involve our own work: [Au(morph) 2 ] [N(SO 2 CH 3 ) 2 ] (refcode DUHKAY; Ahrens et al, 2000) and (morph)AuCN (FIMSUR; Do ¨ring & Jones, 2013). The third is a cationic complex in the salt [Au(morph)(phosphine)][B(C 6 F 5 ) 4 ] (OSOZUS; Hesp & Stradiotto, 2010) whereas the last is the neutral gold(III) complex trans-[AuCl 2 (morph)Ph] (WALQOR; Lavy et al, 2010).…”

Section: Database Surveymentioning

confidence: 99%

“…with the metal atom equatorial to the morpholine ring), whereas just six lay in the range 68-78 � , representing an axial position for the metal residue (with seven further cases in the range 78-90 � , but none with angles < 68 � ; because of structures containing more than one morpholine and/or differing torsion angles, the sum of these exceeds the number of hits). All six axial systems (DUHKAY, Ahrens et al, 2000;FIMSUR, Do ¨ring & Jones, 2013;ICADIB, Miller et al, 2011;REZKUE, Wang & Lian, 2013;YUXWUK and YUXXAR, Wo ¨lper et al, 2010) involved the coinage metals. We made similar observations for piperidine complexes in the CSD (Do ¨ring & Jones, 2023).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structures of the isotypic complexes bis(morpholine)gold(I) chloride and bis(morpholine)gold(I) bromide

Döring,

Jones

2023

Acta Cryst E

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The compounds bis(morpholine-κN)gold(I) chloride, [Au(C4H9NO)2]Cl, 1, and bis(morpholine-κN)gold(I) bromide, [Au(C4H9NO)2]Br, 2, crystallize isotypically in space group C2/c with Z = 4. The gold atoms, which are axially positioned at the morpholine rings, lie on inversion centres (so that the N—Au—N coordination is exactly linear) and the halide anions on twofold axes. The residues are connected by a classical hydrogen bond N—H...halide and by a short gold...halide contact to form a layer structure parallel to the bc plane. The morpholine oxygen atom is not involved in classical hydrogen bonding.

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“…In Table 1, we reported a list of studied onium compounds or coordination complexes in a chronological order. The crystal structure of o-benzenedisulfonimide itself was determined: the five membered 1,3,2-dithiazole ring has an envelope conformation, with the N atom lying outside the mean plane of the S-C-C-S moiety; in the crystal, the molecules are linked by N-H…O hydrogen bonds into chains and in a three-dimensional network [73,74]. The structure of the conjugated anion is described as an essentially planar bicyclic framework [67,72,73,74].…”

Section: Derivativesmentioning

confidence: 99%

o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest

Barbero¹,

Bazzi

Cadamuro

et al. 2011

COC

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ABSTRACT:Synthesized nearly one century ago as a saccharine-like sweetener compound, the obenzenedisulfonimide has received a discontinuous attention in the past. In the last century, various synthetic procedures have been reported, in confirmation of the interest in this intriguing compound. In recent years, it has been used as a leaving group in reactions of nucleophilic substitution of amines with alcohols or phenols to give the corresponding ethers. Its Nfluoroderivative is a stable and efficient fluorinating agent, which has found applications in several asymmetric syntheses. In previous studies, its conjugated base has been extensively used as stabilizing counter-ion of arenediazonium salts; safely isolated and stored in a dry state, ready to use, they have been applied successfully in many dediazoniation reactions, with interesting mechanistic insights. More recently, due to its high acidity, the o-benzenedisulfonimide has been used in catalytic amounts in some common acid-catalyzed organic reactions. Valuable aspects of this catalyst are its easy recovery from the reaction mixture and its reuse in other reactions, with clear economic and ecological advantages. Finally, the disulfonimide functional group has been proposed as a powerful chiral motif for strong Brønsted acids in asymmetric organocatalysis.

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Hydrogen Bonding Networks in Bis(amine)gold(I) Complexes with Disulfonylamide Anions

Cited by 31 publications

References 30 publications

Crystal structures of five halido gold complexes involving piperidine or pyrrolidine as ligands or (protonated) as cations

Crystal structures of five halido gold complexes involving piperidine or pyrrolidine as ligands or (protonated) as cations

Crystal structures of the isotypic complexes bis(morpholine)gold(I) chloride and bis(morpholine)gold(I) bromide

o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest

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