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Graham Smith - One of the best experts on this subject based on the ideXlab platform.
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Transfer Compound of 5-Sulfosalicylic Acid with 4-Aminopyridine.
2015Co-Authors: Graham SmithAbstract:Smith, Graham (2011) Pseudo-merohedral twinning in the structure of the hydrated 1:1 proton-transfer compound of 5-Sulfosalicylic Acid with 4-aminopyridine. Journal of Chemical Crystallography, 41(3), pp. 359-363. © Copyright 2011 Springer Verla
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Hydrogen Bonding in Proton-Transfer Compounds of 5-Sulfosalicylic Acid with a Series of Aliphatic Nitrogen Lewis Bases.
2015Co-Authors: Graham Smith, Urs D Wermuth, Dalius S. SagatysAbstract:proton-transfer compounds of 5-Sulfosalicylic Acid with a series of aliphatic nitroge
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Crystal structures and hydrogen bonding in the proton-transfer salts of nicotine with 3,5-dinitrosalicylic Acid and 5-Sulfosalicylic Acid
International Union of Crystallography, 2014Co-Authors: Graham Smith, Urs D WermuthAbstract:The structures of the 1:1 anhydrous salts of nicotine (NIC) with 3,5-dinitrosalicylic Acid (DNSA) and 5-Sulfosalicylic Acid (5-SSA), namely (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 2-carboxy-4,6-dinitrophenolate, C10H15N2+·C7H3N2O7−, (I), and (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate, C10H15N2+·C7H5O6S−, (II), are reported. The asymmetric units of both (I) and (II) comprise two independent nicotinium cations (C and D) and either two DNSA or two 5-SSA anions (A and B), respectively. One of the DNSA anions shows a 25% rotational disorder in the benzene ring system. In the crystal of (I), inter-unit pyrrolidinium N—H...Npyridine hydrogen bonds generate zigzag NIC cation chains which extend along a, while the DNSA anions are not involved in any formal inter-species hydrogen bonding but instead form π–π-associated stacks which are parallel to the NIC cation chains along a [ring-centroid separation = 3.857 (2) Å]. Weak C—H...O interactions between chain substructures give an overall three-dimensional structure. In the crystal of (II), A and B anions form independent zigzag chains with C and D cations, respectively, through carboxylic Acid O—H...Npyridine hydrogen bonds. These chains, which extend along b, are pseudocentrosymmetrically related and give π–π interactions between the benzene rings of anions A and B and the pyridine rings of the NIC cations C and D, respectively [ring centroid separations = 3.6422 (19) and 3.7117 (19) Å]. Also present are weak C—H...O hydrogen-bonding interactions between the chains, giving an overall three-dimensional structure
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proton transfer versus nontransfer in compounds of the diazo dye precursor 4 phenyldiazenyl aniline aniline yellow with strong organic Acids the 5 sulfosalicylate and the dichroic benzenesulfonate salts and the 1 2 adduct with 3 5 dinitrobenzoic Acid
Acta Crystallographica Section C-crystal Structure Communications, 2009Co-Authors: Graham Smith, Urs D Wermuth, David J Young, Jonathan M WhiteAbstract:The structures of two 1:1 proton-transfer red-black dye compounds formed by reaction of aniline yellow [4-(phenyldiazenyl)aniline] with 5-Sulfosalicylic Acid and benzenesulfonic Acid, and a 1:2 nontransfer adduct compound with 3,5-dinitrobenzoic Acid have been determined at either 130 or 200 K. The compounds are 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 3-carboxy-4-hydroxybenzenesulfonate methanol solvate, C12H12N3+.C7H5O6S-.CH3OH, (I), 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 4-(phenyldiazenyl)anilinium bis(benzenesulfonate), 2C12H12N3+.2C6H5O3S-, (II), and 4-(phenyldiazenyl)aniline-3,5-dinitrobenzoic Acid (1/2), C12H11N3.2C7H4N2O6, (III). In compound (I), the diazenyl rather than the aniline group of aniline yellow is protonated, and this group subsequently takes part in a primary hydrogen-bonding interaction with a sulfonate O-atom acceptor, producing overall a three-dimensional framework structure. A feature of the hydrogen bonding in (I) is a peripheral edge-on cation-anion association also involving aromatic C-H...O hydrogen bonds, giving a conjoint R(1)(2)(6)R(1)(2)(7)R(2)(1)(4) motif. In the dichroic crystals of (II), one of the two aniline yellow species in the asymmetric unit is diazenyl-group protonated, while in the other the aniline group is protonated. Both of these groups form hydrogen bonds with sulfonate O-atom acceptors and these, together with other associations, give a one-dimensional chain structure. In compound (III), rather than proton transfer, there is preferential formation of a classic R(2)(2)(8) cyclic head-to-head hydrogen-bonded carboxylic Acid homodimer between the two 3,5-dinitrobenzoic Acid molecules, which, in association with the aniline yellow molecule that is disordered across a crystallographic inversion centre, results in an overall two-dimensional ribbon structure. This work has shown the correlation between structure and observed colour in crystalline aniline yellow compounds, illustrated graphically in the dichroic benzenesulfonate compound.
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4-(2-Hydroxyethyl)anilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
International Union of Crystallography, 2009Co-Authors: Urs D Wermuth, Graham SmithAbstract:In the structure of the title compound, C8H12NO+·C7H5O6S−·H2O, isolated from the reaction of 2-(4-aminophenyl)ethanol with 5-Sulfosalicylic Acid, the cations form head-to-tail hydrogen-bonded chains through C11(9) anilinium N+—H...Ohydroxyl interactions while the anions also form parallel but C11(8)-linked chains through carboxylic Acid O—H...Osulfonate interactions. These chains inter-associate through a number of N+—H...O and O—H...O bridging interactions, giving a two-dimensional array in the ab plane
Smith Graham - One of the best experts on this subject based on the ideXlab platform.
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Proton-transfer compounds featuring the unusual 4-arsonoanilinium cation from the reaction of (4-aminophenyl) arsonic Acid with strong organic Acids
De Gruyter, 2018Co-Authors: Smith Graham, Wermuth UrsAbstract:The crystal structures of the 1:1 proton-transfer compounds of (4-aminophenyl)arsonic Acid (p-arsanilic Acid) with the strong organic Acids, 2,4,6-trinitrophenol (picric Acid), 3,5-dinitrosalicylic Acid, (3-carboxy-4-hydroxy)benzenesulfonic Acid (5-Sulfosalicylic Acid) and toluene-4-sulfonic Acid have been determined at 200 K and their hydrogen–bonding patterns examined. The compounds are, respectively, anhydrous 4-arsonoanilinium 2,4,6-trinitrophenolate (1), the hydrate 4-arsonoanilinium 2-carboxy-4,6-dinitrophenolate monohydrate (2), the hydrate 4-arsonoanilinium (3-carboxy-4-hydroxy)benzenesulfonate monohydrate (3) and the partial solvate 4-arsonoanilinium toluene-4-sulfonate 0.8 hydrate (4). The asymmetric unit of 2, a phenolate, comprises two independent but conformationally similar cation-anion pairs and two water molecules of solvation, and in all compounds, extensive inter-species hydrogen–bonding interactions involving arsono O–H···O and anilinium N–H···O hydrogen–bonds generate three-dimensional supramolecular structures. In the cases of 1 and 2, the acceptors include phenolate and nitro O-atom acceptors, with 3 and 4, additionally, sulfonate O-atom acceptors, and with the hydrates 2–4, the water molecules of solvation. A feature of the hydrogen–bonding in 3 is the presence of primary chains extending along (010) through centrosymmetric cyclic R22(8) motifs together with conjoined cyclic R34(12) motifs, which include the water molecule of solvation. The primary hydrogen–bonding in the substructure of 4 involves homomolecular cation–cation arsono O–H···O interactions forming columns down the crystallographic four-fold axis of the unit cell.Full Tex
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Hydrogen bonding in two ammonium salts of 5-Sulfosalicylic Acid : ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate and triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate
Blackwell Publishing on behalf of I.U.Cr, 2013Co-Authors: Smith Graham, Wermuth, Urs D.Abstract:The structures of two ammonium salts of 3-carboxy-4-hydroxybenzenesulfonic Acid (5-Sulfosalicylic Acid, 5-SSA) have been determined at 200 K. In the 1:1 hydrated salt, ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate, NH4+·C7H5O6S-·H2O, (I), the 5-SSA- monoanions give two types of head-to-tail laterally linked cyclic hydrogen-bonding associations, both with graph-set R44(20). The first involves both carboxylic Acid O-HOwater and water O-HOsulfonate hydrogen bonds at one end, and ammonium N-HOsulfonate and N-HOcarboxy hydrogen bonds at the other. The second association is centrosymmetric, with end linkages through water O-HOsulfonate hydrogen bonds. These conjoined units form stacks down c and are extended into a three-dimensional framework structure through N-HO and water O-HO hydrogen bonds to sulfonate O-atom acceptors. Anhydrous triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate, 3NH4+·C7H4O6S2-·C7H5O6S-, (II), is unusual, having both dianionic 5-SSA2- and monoanionic 5-SSA- species. These are linked by a carboxylic Acid O-HO hydrogen bond and, together with the three ammonium cations (two on general sites and the third comprising two independent half-cations lying on crystallographic twofold rotation axes), give a pseudo-centrosymmetric asymmetric unit. Cation-anion hydrogen bonding within this layered unit involves a cyclic R33(8) association which, together with extensive peripheral N-HO hydrogen bonding involving both sulfonate and carboxy/carboxylate acceptors, gives a three-dimensional framework structure. This work further demonstrates the utility of the 5-SSA- monoanion for the generation of stable hydrogen-bonded crystalline materials, and provides the structure of a dianionic 5-SSA2- species of which there are only a few examples in the crystallographic literature
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Hydrogen bonding in proton-transfer compounds of 5-Sulfosalicylic Acid with a series of aliphatic nitrogen Lewis bases
Kluwer, 2011Co-Authors: Smith Graham, Wermuth, Urs D., Sagatys, Dalius S.Abstract:The crystal structures of the proton-transfer compounds of 5-Sulfosalicylic Acid (3-carboxy-4-hydroxybenzenesulfonic Acid) with the aliphatic nitrogen Lewis bases, hydroxylamine, triethylamine, pyrrolidine, morpholine, N-methylmorpholine and piperazine, viz. hydroxyammonium 3-carboxy-4-hydroxybenzenesulfonate (1), triethylaminium 3-carboxy-4-hydroxybenzenesulfonate (2), pyrrolidinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate (3), morpholinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate (4), N-methylmorpholinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate (5) and piperazine-1,4-diium bis(3-carboxy-4-hydroxybenzenesulfonate) hexahydrate (6) have been determined and their comparative structural features and hydrogen-bonding patterns described. Crystals of 4 are triclinic, space group P-1 while the remainder are monoclinic with space group either P21/c (1 - 3) or P21/n (5, 6). Unit cell dimensions and contents are: for 1, a = 5.0156(3), b = 10.5738(6), c = 18.4785(9) Å, β = 96.412(5)o, Z = 4; for 2, a = 8.4998(4), b = 12.3832(6), c = 15.4875(9) Å, β = 102.411(5)o, Z = 4; for 3, a = 6.8755(2), b = 15.5217(4), c = 12.8335(3) Å, β = 92.074(2)o, Z = 4; for 4, a = 6.8397(2), b = 12.9756(5), c = 15.8216(6) Å, α = 90.833(3), β = 95.949(3), γ = 92.505(3)o, Z = 4; for 5, a = 7.0529(3), b = 13.8487(7), c = 15.6448(6) Å, β = 90.190(6)o, Z = 4; for 6, a = 7.0561(2), b = 15.9311(4), c = 12.2102(3) Å, β = 100.858(3)o, Z = 2. The hydrogen bonding generates structures which are either two-dimensional (2 and 5) or three-dimensional (1, 3, 4 and 6). Compound 6 represents the third reported structure of a salt of 5-Sulfosalicylic Acid having a dicationic piperazine species. \u
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Pseudo-merohedral twinning in the structure of the hydrated 1:1 proton-transfer compound of 5-Sulfosalicylic Acid with 4-aminopyridine
'Springer Science and Business Media LLC', 2011Co-Authors: Smith GrahamAbstract:The structure of the pseudo-merohedrally twinned crystal of the 1:1 proton-transfer compound of 5-Sulfosalicylic Acid (3-carboxy-4-hydroxybenzenesulfonic Acid) with 4-aminopyridine: 4-aminopyridinium 3-carboxy-4-hydroxybenzenesulfonate sesquihydrate has been determined at 180 K and the hydrogen-bonding pattern is described. Crystals of the compound are monoclinic with space group P21/c, with unit cell dimensions a = 35.2589(8), b = 7.1948(1), c = 24.5851(5) Å, β = 110.373(2)o, and Z = 16. The monoclinic asymmetric unit comprises four cation-anion pairs and six water molecules of solvation with only the pyridinium cations having pseudo-symmetry as a result of inter-cation aromatic ring π-π stacking effects. Extensive hydrogen bonding gives a three-dimensional framework structure
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4-(2-hydroxyethyl)anilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
'International Union of Crystallography (IUCr)', 2009Co-Authors: Smith Graham, Wermuth UrsAbstract:In the structure of the title compound C8H12NO+ C7H5O6S- . H2O, from the reaction of 2-(4-aminophenyl)ethanol with 5-Sulfosalicylic Acid, the cations form head-to-tail hydrogen-bonded chains through C1/1(9) anilinium N+-H...O(hydroxyl} interactions while the anions also form similar but C1/1(8)-linked chains through carboxylic Acid O-..O(sulfonate) interactions. The chains inter-associate through a number of N-H...O and O-H...O bridging interactions giving a two-dimensional array in the ab plane
Jonathan M White - One of the best experts on this subject based on the ideXlab platform.
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proton transfer versus nontransfer in compounds of the diazo dye precursor 4 phenyldiazenyl aniline aniline yellow with strong organic Acids the 5 sulfosalicylate and the dichroic benzenesulfonate salts and the 1 2 adduct with 3 5 dinitrobenzoic Acid
Acta Crystallographica Section C-crystal Structure Communications, 2009Co-Authors: Graham Smith, Urs D Wermuth, David J Young, Jonathan M WhiteAbstract:The structures of two 1:1 proton-transfer red-black dye compounds formed by reaction of aniline yellow [4-(phenyldiazenyl)aniline] with 5-Sulfosalicylic Acid and benzenesulfonic Acid, and a 1:2 nontransfer adduct compound with 3,5-dinitrobenzoic Acid have been determined at either 130 or 200 K. The compounds are 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 3-carboxy-4-hydroxybenzenesulfonate methanol solvate, C12H12N3+.C7H5O6S-.CH3OH, (I), 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 4-(phenyldiazenyl)anilinium bis(benzenesulfonate), 2C12H12N3+.2C6H5O3S-, (II), and 4-(phenyldiazenyl)aniline-3,5-dinitrobenzoic Acid (1/2), C12H11N3.2C7H4N2O6, (III). In compound (I), the diazenyl rather than the aniline group of aniline yellow is protonated, and this group subsequently takes part in a primary hydrogen-bonding interaction with a sulfonate O-atom acceptor, producing overall a three-dimensional framework structure. A feature of the hydrogen bonding in (I) is a peripheral edge-on cation-anion association also involving aromatic C-H...O hydrogen bonds, giving a conjoint R(1)(2)(6)R(1)(2)(7)R(2)(1)(4) motif. In the dichroic crystals of (II), one of the two aniline yellow species in the asymmetric unit is diazenyl-group protonated, while in the other the aniline group is protonated. Both of these groups form hydrogen bonds with sulfonate O-atom acceptors and these, together with other associations, give a one-dimensional chain structure. In compound (III), rather than proton transfer, there is preferential formation of a classic R(2)(2)(8) cyclic head-to-head hydrogen-bonded carboxylic Acid homodimer between the two 3,5-dinitrobenzoic Acid molecules, which, in association with the aniline yellow molecule that is disordered across a crystallographic inversion centre, results in an overall two-dimensional ribbon structure. This work has shown the correlation between structure and observed colour in crystalline aniline yellow compounds, illustrated graphically in the dichroic benzenesulfonate compound.
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polymeric structures in the metal complexes of 5 sulfosalicylic Acid the rubidium i caesium i and lead ii analogues
Polyhedron, 2007Co-Authors: Graham Smith, Urs D Wermuth, David J Young, Jonathan M WhiteAbstract:The complexes of 3-carboxy-4-hydroxybenzenesulfonic Acid (5-Sulfosalicylic Acid, H3SSSA) with rubidium(I), caesium(I) and lead(II) have been synthesized and characterized using single crystal X-ray methods at 130 K. The rubidium(I) complex 1, [Rb3(H2SSA)(HSSA)(H2O)4]n, is an unstable hydrate variant of a previously described complex [Rb(H2SSA)(H2O]n, and comprises three independent and different seven-coordinate metal polyhedra interlinked through oxygen donors of the sulfonate, carboxylate and phenolate groups of the 5-sulfosalicylate ligands (one of which is dianionic, the other monoanionic), and one bridging water, giving a three-dimensional hydrogen-bonded framework polymer structure. The anhydrous caesium(I) complex 2 [Cs(H2SSA)]n, which has breen previously described in a room-temperature determination, has a three-dimensional framework polymer structure based on an irregular Cs-O9 repeating unit. Complex 3 with lead(II), [Pb(H2SSA)2(H2O)]n, forms helical step-polymer ribbon sub-structures having an irregular Pb-O7 coordination centre comprising a single monodentate water and six sulfonate-O donors bridging three separate metals. The carboxylic Acid and phenol substituent groups of the 5-sulfosalicylate ligand link the ribbons peripherally through hydrogen bonds, giving a three-dimensional layered polymer structure.
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molecular recognition in proton transfer compounds of brucine with achiral substituted salicylic Acid analogues
Australian Journal of Chemistry, 2006Co-Authors: Graham Smith, Urs D Wermuth, Peter Conrad Healy, Jonathan M WhiteAbstract:The 1:1 proton-transfer brucinium compounds from the reaction of the alkaloid brucine with 5-nitrosalicylic Acid, 3,5-dinitrosalicylic Acid, and 5-Sulfosalicylic Acid, namely anhydrous brucinium 5-nitrosalicylate (1), brucinium 3,5-dinitrosalicylate monohydrate (2), and brucinium 5-sulfosalicylate trihydrate (3) have been prepared and their crystal structures determined by X-ray crystallography. All structures further demonstrate the selectivity of brucine for meta-substituted benzoic Acids and comprise three-dimensional hydrogen-bonded framework polymers. Two of the compounds (1 and 3) have the previously described undulating brucine sheet host-substructures which incorporate interstitially hydrogen-bonded salicylate anion guest species and additionally in 3 the water molecules of solvation. The structure of 2 differs in having a three-centre brucinium–salicylate anion bidentate N+–H···O(carboxyl) hydrogenbonding association linking the species through interstitial associations involving also the water molecules of solvation. A review of the crystallographic structural literature on strychnine and brucine is also given.
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the 1 1 proton transfer compound of 5 sulfosalicylic Acid with 4 aminobenzoic Acid
Acta Crystallographica Section E-structure Reports Online, 2005Co-Authors: Urs D Wermuth, Jonathan M WhiteAbstract:The crystal structure of the anhydrous 1:1 proton-transfer compound of 5-Sulfosalicylic Acid (3-carboxy-4-hydroxybenzenesulfonic Acid) with 4-aminobenzoic Acid, viz. 4-carboxyanilinium 3-carboxy-4-hydroxybenzenesulfonate, C7H8NO2+·C7H5O6S−, displays a hydrogen-bonded polymeric network structure involving primarily all aminium H-atom donors and sulfonate O-atom acceptors, and is propagated through homomolecular cyclic tail-to-tail interactions between the carboxylic Acid substituent groups of both cation and anion species. In addition, there are some cation–anion π–π stacking associations.
Urs D Wermuth - One of the best experts on this subject based on the ideXlab platform.
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Hydrogen Bonding in Proton-Transfer Compounds of 5-Sulfosalicylic Acid with a Series of Aliphatic Nitrogen Lewis Bases.
2015Co-Authors: Graham Smith, Urs D Wermuth, Dalius S. SagatysAbstract:proton-transfer compounds of 5-Sulfosalicylic Acid with a series of aliphatic nitroge
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Crystal structures and hydrogen bonding in the proton-transfer salts of nicotine with 3,5-dinitrosalicylic Acid and 5-Sulfosalicylic Acid
International Union of Crystallography, 2014Co-Authors: Graham Smith, Urs D WermuthAbstract:The structures of the 1:1 anhydrous salts of nicotine (NIC) with 3,5-dinitrosalicylic Acid (DNSA) and 5-Sulfosalicylic Acid (5-SSA), namely (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 2-carboxy-4,6-dinitrophenolate, C10H15N2+·C7H3N2O7−, (I), and (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate, C10H15N2+·C7H5O6S−, (II), are reported. The asymmetric units of both (I) and (II) comprise two independent nicotinium cations (C and D) and either two DNSA or two 5-SSA anions (A and B), respectively. One of the DNSA anions shows a 25% rotational disorder in the benzene ring system. In the crystal of (I), inter-unit pyrrolidinium N—H...Npyridine hydrogen bonds generate zigzag NIC cation chains which extend along a, while the DNSA anions are not involved in any formal inter-species hydrogen bonding but instead form π–π-associated stacks which are parallel to the NIC cation chains along a [ring-centroid separation = 3.857 (2) Å]. Weak C—H...O interactions between chain substructures give an overall three-dimensional structure. In the crystal of (II), A and B anions form independent zigzag chains with C and D cations, respectively, through carboxylic Acid O—H...Npyridine hydrogen bonds. These chains, which extend along b, are pseudocentrosymmetrically related and give π–π interactions between the benzene rings of anions A and B and the pyridine rings of the NIC cations C and D, respectively [ring centroid separations = 3.6422 (19) and 3.7117 (19) Å]. Also present are weak C—H...O hydrogen-bonding interactions between the chains, giving an overall three-dimensional structure
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proton transfer versus nontransfer in compounds of the diazo dye precursor 4 phenyldiazenyl aniline aniline yellow with strong organic Acids the 5 sulfosalicylate and the dichroic benzenesulfonate salts and the 1 2 adduct with 3 5 dinitrobenzoic Acid
Acta Crystallographica Section C-crystal Structure Communications, 2009Co-Authors: Graham Smith, Urs D Wermuth, David J Young, Jonathan M WhiteAbstract:The structures of two 1:1 proton-transfer red-black dye compounds formed by reaction of aniline yellow [4-(phenyldiazenyl)aniline] with 5-Sulfosalicylic Acid and benzenesulfonic Acid, and a 1:2 nontransfer adduct compound with 3,5-dinitrobenzoic Acid have been determined at either 130 or 200 K. The compounds are 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 3-carboxy-4-hydroxybenzenesulfonate methanol solvate, C12H12N3+.C7H5O6S-.CH3OH, (I), 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 4-(phenyldiazenyl)anilinium bis(benzenesulfonate), 2C12H12N3+.2C6H5O3S-, (II), and 4-(phenyldiazenyl)aniline-3,5-dinitrobenzoic Acid (1/2), C12H11N3.2C7H4N2O6, (III). In compound (I), the diazenyl rather than the aniline group of aniline yellow is protonated, and this group subsequently takes part in a primary hydrogen-bonding interaction with a sulfonate O-atom acceptor, producing overall a three-dimensional framework structure. A feature of the hydrogen bonding in (I) is a peripheral edge-on cation-anion association also involving aromatic C-H...O hydrogen bonds, giving a conjoint R(1)(2)(6)R(1)(2)(7)R(2)(1)(4) motif. In the dichroic crystals of (II), one of the two aniline yellow species in the asymmetric unit is diazenyl-group protonated, while in the other the aniline group is protonated. Both of these groups form hydrogen bonds with sulfonate O-atom acceptors and these, together with other associations, give a one-dimensional chain structure. In compound (III), rather than proton transfer, there is preferential formation of a classic R(2)(2)(8) cyclic head-to-head hydrogen-bonded carboxylic Acid homodimer between the two 3,5-dinitrobenzoic Acid molecules, which, in association with the aniline yellow molecule that is disordered across a crystallographic inversion centre, results in an overall two-dimensional ribbon structure. This work has shown the correlation between structure and observed colour in crystalline aniline yellow compounds, illustrated graphically in the dichroic benzenesulfonate compound.
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4-(2-Hydroxyethyl)anilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
International Union of Crystallography, 2009Co-Authors: Urs D Wermuth, Graham SmithAbstract:In the structure of the title compound, C8H12NO+·C7H5O6S−·H2O, isolated from the reaction of 2-(4-aminophenyl)ethanol with 5-Sulfosalicylic Acid, the cations form head-to-tail hydrogen-bonded chains through C11(9) anilinium N+—H...Ohydroxyl interactions while the anions also form parallel but C11(8)-linked chains through carboxylic Acid O—H...Osulfonate interactions. These chains inter-associate through a number of N+—H...O and O—H...O bridging interactions, giving a two-dimensional array in the ab plane
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polymeric structures in the metal complexes of 5 sulfosalicylic Acid the rubidium i caesium i and lead ii analogues
Polyhedron, 2007Co-Authors: Graham Smith, Urs D Wermuth, David J Young, Jonathan M WhiteAbstract:The complexes of 3-carboxy-4-hydroxybenzenesulfonic Acid (5-Sulfosalicylic Acid, H3SSSA) with rubidium(I), caesium(I) and lead(II) have been synthesized and characterized using single crystal X-ray methods at 130 K. The rubidium(I) complex 1, [Rb3(H2SSA)(HSSA)(H2O)4]n, is an unstable hydrate variant of a previously described complex [Rb(H2SSA)(H2O]n, and comprises three independent and different seven-coordinate metal polyhedra interlinked through oxygen donors of the sulfonate, carboxylate and phenolate groups of the 5-sulfosalicylate ligands (one of which is dianionic, the other monoanionic), and one bridging water, giving a three-dimensional hydrogen-bonded framework polymer structure. The anhydrous caesium(I) complex 2 [Cs(H2SSA)]n, which has breen previously described in a room-temperature determination, has a three-dimensional framework polymer structure based on an irregular Cs-O9 repeating unit. Complex 3 with lead(II), [Pb(H2SSA)2(H2O)]n, forms helical step-polymer ribbon sub-structures having an irregular Pb-O7 coordination centre comprising a single monodentate water and six sulfonate-O donors bridging three separate metals. The carboxylic Acid and phenol substituent groups of the 5-sulfosalicylate ligand link the ribbons peripherally through hydrogen bonds, giving a three-dimensional layered polymer structure.
Wermuth Urs - One of the best experts on this subject based on the ideXlab platform.
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Proton-transfer compounds featuring the unusual 4-arsonoanilinium cation from the reaction of (4-aminophenyl) arsonic Acid with strong organic Acids
De Gruyter, 2018Co-Authors: Smith Graham, Wermuth UrsAbstract:The crystal structures of the 1:1 proton-transfer compounds of (4-aminophenyl)arsonic Acid (p-arsanilic Acid) with the strong organic Acids, 2,4,6-trinitrophenol (picric Acid), 3,5-dinitrosalicylic Acid, (3-carboxy-4-hydroxy)benzenesulfonic Acid (5-Sulfosalicylic Acid) and toluene-4-sulfonic Acid have been determined at 200 K and their hydrogen–bonding patterns examined. The compounds are, respectively, anhydrous 4-arsonoanilinium 2,4,6-trinitrophenolate (1), the hydrate 4-arsonoanilinium 2-carboxy-4,6-dinitrophenolate monohydrate (2), the hydrate 4-arsonoanilinium (3-carboxy-4-hydroxy)benzenesulfonate monohydrate (3) and the partial solvate 4-arsonoanilinium toluene-4-sulfonate 0.8 hydrate (4). The asymmetric unit of 2, a phenolate, comprises two independent but conformationally similar cation-anion pairs and two water molecules of solvation, and in all compounds, extensive inter-species hydrogen–bonding interactions involving arsono O–H···O and anilinium N–H···O hydrogen–bonds generate three-dimensional supramolecular structures. In the cases of 1 and 2, the acceptors include phenolate and nitro O-atom acceptors, with 3 and 4, additionally, sulfonate O-atom acceptors, and with the hydrates 2–4, the water molecules of solvation. A feature of the hydrogen–bonding in 3 is the presence of primary chains extending along (010) through centrosymmetric cyclic R22(8) motifs together with conjoined cyclic R34(12) motifs, which include the water molecule of solvation. The primary hydrogen–bonding in the substructure of 4 involves homomolecular cation–cation arsono O–H···O interactions forming columns down the crystallographic four-fold axis of the unit cell.Full Tex
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4-(2-hydroxyethyl)anilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate
'International Union of Crystallography (IUCr)', 2009Co-Authors: Smith Graham, Wermuth UrsAbstract:In the structure of the title compound C8H12NO+ C7H5O6S- . H2O, from the reaction of 2-(4-aminophenyl)ethanol with 5-Sulfosalicylic Acid, the cations form head-to-tail hydrogen-bonded chains through C1/1(9) anilinium N+-H...O(hydroxyl} interactions while the anions also form similar but C1/1(8)-linked chains through carboxylic Acid O-..O(sulfonate) interactions. The chains inter-associate through a number of N-H...O and O-H...O bridging interactions giving a two-dimensional array in the ab plane
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Proton transfer versus nontransfer in compounds of the diazo-dye precursor 4-(phenyldiazenyl)aniline (aniline yellow) with strong organic Acids: the 5-sulfosalicylate and the dichroic benzenesulfonate salts, and the 1:2 adduct with 3,5-dinitrobenzoic
'International Union of Crystallography (IUCr)', 2009Co-Authors: Smith Graham, Wermuth Urs, Young David, White JonathanAbstract:The structures of two 1:1 proton-transfer red-black dye compounds formed by reaction of aniline yellow [4-(phenyldiazenyl)aniline] with 5-Sulfosalicylic Acid and benzenesulfonic Acid, and a 1:2 nontransfer adduct compound with 3,5-dinitrobenzoic Acid have been determined at either 130 or 200 K. The compounds are 2-(4-aminophenyl)-1-phenylhydrazin-1-ium 3-carboxy-4-hydroxybenzenesulfonate methanol solvate, C12H12N3+.C7H5O6S-.CH3OH (I), 2-(4-aminophenyl)-1-hydrazin-1-ium 4-(phenydiazinyl)anilinium bis(benzenesulfonate), 2C12H12N3+.2C6H5O3S-, (II) and 4-(phenyldiazenyl)aniline-3,5-dinitrobenzoic Acid (1/2) C12H11N3.2C~7~H~4~N~2~O~6~, (III). In compound (I) the diaxenyl rather than the aniline group of aniline yellow is protonated and this group subsequently akes part in a primary hydrogen-bonding interaction with a sulfonate O-atom acceptor, producing overall a three-dimensional framework structure. A feature of the hydrogen bonding in (I) is a peripheral edge-on cation-anion association involving aromatic C--H...O hydrogen bonds, giving a conjoint R1/2(6)R1/2(7)R2/1(4)motif. In the dichroic crystals of (II), one of the two aniline yellow species in the asymmetric unit is diazenyl-group protonated while in the other the aniline group is protonated. Both of these groups form hydrogen bonds with sulfonate O-atom acceptors and thee, together with other associations give a one-dimensional chain structure. In compound (III), rather than proton-transfer, there is a preferential formation of a classic R2/2(8) cyclic head-to-head hydrogen-bonded carboxylic Acid homodimer between the two 3,5-dinitrobenzoic Acid molecules, which in association with the aniline yellow molecule that is disordered across a crystallographic inversion centre, result in an overall two-dimensional ribbon structure. This work has shown the correlation between structure and observed colour in crystalline aniline yellow compounds, illustrated graphically in the dichroic benzenesulfonate compound
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Hydrogen Bonding in Proton Transfer Compounds of 5 Sulfosalicylic Acid With Ortho-Substituted Moocyclic Heteroaromatic Lewis Bases
'Springer Science and Business Media LLC', 2006Co-Authors: Smith Graham, Wermuth Urs, Healy PeterAbstract:The crystal structures of the 1:1 proton-transfer compounds of 5-Sulfosalicylic Acid with the ortho-substituted monocyclic heteroaromatic Lewis bases, 2-aminopyridine, 2- hydroxypyridine and 2-aminopyrimidine, viz. 2-aminopyridinium 5-sulfosalicylate (1), 2-hydroxypyridinium 5-sulfosalicylate monohydrate (2) and 2-aminopyrimidinium 5- sulfosalicylatemonohydrate (3) have been determined and their hydrogen-bonding patterns described. All compounds are monoclinic, space group P21/c, with Z=4 in cells with dimensions a=7.898(5), b=11.159(11), c=14.912(7) A° , β =96.849(11)◦ (1);=7.260(2), b=15.292(3), c=12.615(2) A° , β =102.45(5)◦ (2) and a=7.0430(7), b=12.1871(16), c=16.2825(12) A° , β =101.364(7)◦ (3). All three compounds show some molecular disorder, in 1 within the cation species and with both 2 and 3, a similar rotational disorder in the anion sulfonate group. Hydrogen bonding in all three compounds together with significant cation-anion or cation-cation inter-ring π–π interactions generate three-dimensional layered polymer structures
