02436nas a2200277   4500008004100000022001400041245017600055210006900231260006700300300001000367490000700377520139300384653001801777653001401795653002201809653003201831653002101863653002101884653001701905653002601922100002301948700001701971700002401988700002702012856011902039       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<p>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.</p>10aacyl transfer10acocrystal10acrystal structure10adesign of functional solids10ahelical assembly10ahydrogen bonding10amyo-inositol10asolid-state reactions1 aTamboli, Majid, I.1 aBahadur, Vir1 aGonnade, Rajesh, G.1 aShashidhar, Mysore, S.  uhttp://library.ncl.res.in/content/correlation-solid-state-reactivities-racemic-246-di-o-benzoyl-myo-inositol-135-002399nas a2200181   4500008004100000022001400041245024500055210006900300260007100369300001400440490000700454520154000461100002302001700001702024700002402041700002702065856012502092       2015                        eng d  a1528-748300aCocrystallization of 2,3-dihydroxynaphthalene with its para-, meta-, and ortho-ditoluates: insight into cocrystal formation and clues for the construction of supramolecular assemblies capable of intermolecular acyl group transfer reactivity0 aCocrystallization of 23dihydroxynaphthalene with its para meta a  a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcMAR  a1226-12320 v153 a<p>2,3-Dihydroxynaphthalene forms 2:1 cocrystals with its p-ditoluate and 1:1 cocrystals with its m-ditoluate but not with the o-ditoluate. In 2:1 cocrystals of the p-ditoluate, naphthalene diol molecules form a dimeric motif through OH...O hydrogen bonding interactions. The adjacent dimers sandwich the molecules of p-ditoluate through C-H...pi interactions. In 1:1 cocrystals of the m-ditoluate, naphthalene diol molecules generate a zigzag pattern through O-H...O hydrogen bonding interaction involving -OH of the diol and the C=O of the m-ditoluate. Intermolecular toluoyl group transfer reaction was more facile in cocrystals of the p-ditoluate as compared to cocrystals of the m-ditoluate. This difference in reactivity is consistent with the relative geometry of the electrophile (El, C-O) and the nucleophile (Nu, OH) in these cocrystals. A comparison of the cocrystallization behavior and structure of the two cocrystals with their constituents suggests that the position of the methyl group is crucial for cocrystal formation. A survey of the CSD revealed that the incidence of polymorphism and cocrystals formation decreases (number of hits) in the order para- &gt; ortho- &gt; meta- for disubstituted benzene derivatives. This suggests that compounds prone to exhibit polymorphism have more propensities to form cocrystals as compared to those that resist polymorphism. This information could be useful while selecting cocrystal formers and construction of supramolecular functional assemblies with desired properties.</p>1 aTamboli, Majid, I.1 aBahadur, Vir1 aGonnade, Rajesh, G.1 aShashidhar, Mysore, S.  uhttp://library.ncl.res.in/content/cocrystallization-23-dihydroxynaphthalene-its-para-meta-and-ortho-ditoluates-insight-000794nas a2200169   4500008004100000022001400041245026000055210006900315260000800384300000900392490000700401100002300408700001700431700002400448700002700472856012500499       2019                        eng d  a1528-748300aCocrystallization of 2,3-dihydroxynaphthalene with its para-, meta-, and ortho-ditoluates: insight into cocrystal formation and clues for the construction of supramolecular assemblies capable of intermolecular acyl group transfer reactivity (vol 15, pg 120 aCocrystallization of 23dihydroxynaphthalene with its para meta a  cOCT  a59980 v191 aTamboli, Majid, I.1 aBahadur, Vir1 aGonnade, Rajesh, G.1 aShashidhar, Mysore, S.  uhttp://library.ncl.res.in/content/cocrystallization-23-dihydroxynaphthalene-its-para-meta-and-ortho-ditoluates-insight-101996nas a2200265   4500008004100000022001400041245015900055210006900214260000800283300001400291490000700305520103700312653001401349653002101363653003201384653002601416653002601442653002201468100001701490700002401507700001901531700002701550700002701577856012601604       2021                        eng d  a2192-650600aConstruction of two-component chemically reactive supramolecular assemblies-acyl migration reactions in cocrystals of napthalene-2,3-diol and its diesters0 aConstruction of twocomponent chemically reactive supramolecular   cAUG  a1128-11340 v863 aReactions in solids are of contemporary interest due to applications in pharmaceutical industries to environmental sustainability. Although several reactive crystals that support chemical reactions have been identified and characterized, the same cannot be said about reactive cocrystals. Earlier we correlated the facile acyl group transfer reactions in crystals with supramolecular parameters obtained from the crystal structures. The structure-reactivity correlation revealed the requirement of proper juxtaposition of electrophile (C=O) and the nucleophile (OH) with distance (similar to 3.2 angstrom) and angle (similar to 90 degrees) along the chain structure. The current article describes the preparation of cocrystals that are capable of supporting intermolecular acyl group transfer reactions in a group of structurally similar molecules. The cocrystals of naphthalene 2,3-diol and its corresponding diesters showed a facile solid state acyl transfer reaction, which has been well correlated with their crystal structures.10aAcylation10adomino reactions10aintermolecular interactions10areaction in cocrystal10asolid-state reactions10aX-ray diffraction1 aBahadur, Vir1 aGonnade, Rajesh, G.1 aTamboli, Majid1 aKrishnaswamy, Shobhana1 aShashidhar, Mysore, S.  uhttp://library.ncl.res.in/content/construction-two-component-chemically-reactive-supramolecular-assemblies-acyl-migration