01922nas a2200265 4500008004100000022001400041245010100055210006900156260007300225300001200298490000800310520097200318653001301290653002301303653002301326653002101349653001801370100002101388700002301409700002401432700002301456700002401479700002201503856013101525 2010 eng d a0022-286000aCrystal structure, NMR and theoretical investigations on 2-(o-hydroxy-anilino)-1,4-napthoquinone0 aCrystal structure NMR and theoretical investigations on 2ohydrox aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcMAR a144-1510 v9663 a

Crystal structure, (1)H NMR and cyclic voltammetric investigations of 2-(o-hydroxy-anilino)-1,4-napthoquinone (HAN), resulting from coupling of aminophenol with 2-hydroxy-1,4-napthoquinone, have been carried out. X-ray structure reveals that the HAN ligand crystallizes in orthorhombic space group Pca2(1) with Z = 4. forming a chain via inter-molecular O2 center dot center dot center dot H1A-O1 and C15-H15 center dot center dot center dot O3 interactions. Both (1)H NMR and cyclic voltammetry experiments suggest the titled ligand is associated and exists as dinner in d(6)-DMSO while the monomer has been predicted in CDCl(3) solution. Density functional calculations can be utilized to gauge the strength of hydrogen-bonded interactions from the (1)H chemical shifts in the NMR spectra. Self-consistent reaction field (SCRF) calculations further support the inferences drawn from cyclic voltammetry experiments. (C) 2009 Elsevier B.V. All rights reserved.

10a(1)H NMR10acyclic voltammetry10aDensity functional10ahydrogen bonding10aNapthoquinone1 aFeizi, Nourollah1 aPinjari, Rahul, V.1 aGejji, Shridhar, P.1 aSayyed, Fareed, B.1 aGonnade, Rajesh, G.1 aRane, Sandhya, Y. uhttps://library.ncl.res.in/content/crystal-structure-nmr-and-theoretical-investigations-2-o-hydroxy-anilino-14-napthoquinone-002437nas a2200277 4500008004100000022001400041245017600055210006900231260006700300300001000367490000700377520139300384653001801777653001401795653002201809653003201831653002101863653002101884653001701905653002601922100002301948700001701971700002401988700002702012856012002039 2014 eng d a0108-270100aCorrelation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4 `-bipyridine cocrystal with their crystal structures0 aCorrelation of the solidstate reactivities of racemic 246diObenz a111 RIVER ST, HOBOKEN 07030-5774, NJ USAbWILEY-BLACKWELLcNOV a1040+0 v703 a

Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8, (1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4 `-bipyridine molecules in its cocrystal, C21H18O8 center dot C10H8N2, (1)center dot BP, inhibits the intermolecular benzoyl-group transfer reaction. In (1), molecules are assembled around the crystallographic twofold screw axis (b axis) to form a helical self-assembly through conventional O-H center dot center dot center dot O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy group (nucleophile, Nu) in proximity, with a preorganized El center dot center dot center dot Nu geometry favourable for the acyl transfer reaction. In the cocrystal (1)center dot BP, the dibenzoate and bipyridine molecules are arranged alternately through OH center dot center dot center dot N interactions. The presence of the bipyridine molecules perturbs the regular helical assembly of the dibenzoate molecules and thus restricts the solid-state reactivity. Hence, unlike the parent dibenzoate crystals, the cocrystals do not exhibit benzoyl-transfer reactions. This approach is useful for increasing the stability of small molecules in the crystalline state and could find application in the design of functional solids.

10aacyl transfer10acocrystal10acrystal structure10adesign of functional solids10ahelical assembly10ahydrogen bonding10amyo-inositol10asolid-state reactions1 aTamboli, Majid, I.1 aBahadur, Vir1 aGonnade, Rajesh, G.1 aShashidhar, Mysore, S. uhttps://library.ncl.res.in/content/correlation-solid-state-reactivities-racemic-246-di-o-benzoyl-myo-inositol-135-004390nas a2200265 4500008004100000022001400041245017900055210006900234260007400303300001400377490000700391520332100398653003003719653004303749653001403792653002203806653002103828653002603849653002303875653002803898100002503926700002403951700002403975856012503999 2015 eng d a2053-229600aCrystal structures of the pyrazinamide-p-aminobenzoic acid (1/1) cocrystal and the transamidation reaction product 4-(pyrazine-2-carboxamido)-benzoic acid in the molten state0 aCrystal structures of the pyrazinamidepaminobenzoic acid 11 cocr a2 ABBEY SQ, CHESTER, CH1 2HU, ENGLANDbINT UNION CRYSTALLOGRAPHYcNOV a1010-U2760 v713 a

The synthesis of pharmaceutical cocrystals is a strategy to enhance the performance of active pharmaceutical ingredients (APIs) without affecting their therapeutic efficiency. The 1: 1 pharmaceutical cocrystal of the antituberculosis drug pyrazinamide (PZA) and the cocrystal former p-aminobenzoic acid (p-ABA), C7H7NO2- C5H5N3O, (1), was synthesized successfully and characterized by relevant solid-state characterization methods. The cocrystal crystallizes in the monoclinic space group P21/n containing one molecule of each component. Both molecules associate via intermolecular O-H center dot center dot center dot O and NH center dot center dot center dot O hydrogen bonds [O center dot center dot center dot O = 2.6102 (15)angstrom and O-H center dot center dot center dot O = 168.3 (19)degrees; N center dot center dot center dot O = 2.9259 (18) angstrom and N-H center dot center dot center dot O = 167.7 (16)degrees] to generate a dimeric acidamide synthon. Neighbouring dimers are linked centrosymmetrically through N-H center dot center dot center dot O interactions [N center dot center dot center dot O = 3.1201 (18) angstrom and N-H center dot center dot center dot O = 136.9 (14)degrees] to form a tetrameric assembly supplemented by C-H center dot center dot center dot N interactions [C center dot center dot center dot N = 3.5277 (19) angstrom and C-H center dot center dot center dot N = 147 degrees]. Linking of these tetrameric assemblies through N-H center dot center dot center dot O [N center dot center dot center dot O = 3.3026 (19) angstrom and N-H center dot center dot center dot O = 143.1 (17)degrees], NH center dot center dot center dot N [N center dot center dot center dot N = 3.221 (2) angstrom and N-H center dot center dot center dot N = 177.9 (17)degrees] and C-H center dot center dot center dot O [C center dot center dot center dot O = 3.5354 (18) angstrom and C-H center dot center dot center dot O = 152 degrees] interactions creates the twodimensional packing. Recrystallization of the cocrystals from the molten state revealed the formation of 4-(pyrazine-2-carboxamido) benzoic acid, C12H9N3O3, (2), through a transamidation reaction between PZA and p-ABA. Carboxamide (2) crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. Molecules of (2) form a centrosymmetric dimeric homosynthon through an acid-acid O-H center dot center dot center dot O hydrogen bond [O center dot center dot center dot O = 2.666 (3) angstrom and O-H center dot center dot center dot O = 178 (4) degrees]. Neighbouring assemblies are connected centrosymmetrically via a C-H center dot center dot center dot N interaction [C center dot center dot center dot N = 3.365 (3) angstrom and C-H center dot center dot center dot N = 142 degrees] engaging the pyrazine groups to generate a linear chain. Adjacent chains are connected loosely via C-H center dot center dot center dot O interactions [C center dot center dot center dot O = 3.212 (3) angstrom and CH center dot center dot center dot O = 149 degrees] to generate a two-dimensional sheet structure. Closely associated two-dimensional sheets in both compounds are stacked via aromatic pi-stacking interactions engaging the pyrazine and benzene rings to create a threedimensional multi-stack structure.

10aacid-amide hetero-synthon10aactive pharmaceutical ingredient (API)10acocrystal10acrystal structure10ahydrogen bonding10amolten-state reaction10apowder diffraction10atransamidation reaction1 aThorat, Shridhar, H.1 aSahu, Sanjay, Kumar1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/crystal-structures-pyrazinamide-p-aminobenzoic-acid-11-cocrystal-and-transamidation-102698nas a2200289 4500008004100000022001400041245016000055210006900215260007300284300001200357490000900369520162800378653002402006653001602030653002102046653001902067653001902086653001102105100001602116700002002132700001702152700003102169700002402200700002502224700002702249856013202276 2016 eng d a0022-286000aNaphthoquinone based chemosensor 2-(2 `-aminoethylpyridine)-3-chloro-1,4-naphthoquinone: detection of metal ions, X-ray -crystal structures and DFT studies0 aNaphthoquinone based chemosensor 22 aminoethylpyridine3chloro14n aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcJUN a132-1430 v11143 a

Naphthoquinone based Chemosensor 2; 2-(2'-aminoethylpyridine)-3-chloro-1,4-napthoquinone have been synthesized and characterized. Chemosensor 2 crystallizes in the orthorhombic space group Pbcn and shows extensive intramolecular as well as intermolecular hydrogen bonding interactions. Each molecule of Chemosensor 2 showed interaction with five neighboring molecules via C-H center dot center dot center dot N, N-H center dot center dot center dot N, C-H center dot center dot center dot Cl and C-H center dot center dot center dot O interactions. Slipped pi-pi stacking interaction was observed in adjacent quinonoid and benzenoid rings. Chemosensor abilities of Chemosensor 2 ligand have been evaluated with metal ions viz. Cu2+, Ni2+, Zn2+, Co2+, Fe3+, Mn2+, Cr3+, Hg2+, La3+ and Cd2+ in methanol, methanol-water mixture and in presence of mild base triethylamine. Stoichiometry of Chemosensor 2 with metal ions such as Cu2+, Ni2+, Zn2+ and Co2+ ions was determined by Jobs method in methanol and were found as 1:1 for Cu2+ and 2:1 for Ni2+, Zn2+ Co2+. The variation in the metal ligand ratio is observed in aqueous media for Cu2+. Chemosensor 2 can be used selectively for naked eye detection of Cu2+ ions. The association constant obtained in methanol shows the trend Cu2+>Ni2+>Co2+. Cu2+ and two (Ni-1 and Ni-2) Ni2+ complexes were synthesized. Ni-2 complex showed coordination of Chemosensor 2 ligands was through pyridine nitrogen's only. The Chemosensor 2 and its deprotonated forms in methanol, water and triethylamine were also studied by TD-DFT studies. (C) 2016 Elsevier B.V. All rights reserved.

10aAminonaphthoquinone10aChemosensor10ahydrogen bonding10aNaphthoquinone10api-pi stacking10aTD-DFT1 aPatil, Amit1 aWare, Anuja, P.1 aBhand, Sujit1 aChakravarty, Debamitra, K.1 aGonnade, Rajesh, G.1 aPingale, Subhash, S.1 aSalunke-Gawali, Sunita uhttps://library.ncl.res.in/content/naphthoquinone-based-chemosensor-2-2-aminoethylpyridine-3-chloro-14-naphthoquinone-detection