@article { ISI:000296738500014,
	title = {Comparison of racemic epi-inosose and (-)-epi-inosose},
	journal = {ACTA Crystallographica Section C-Crystal Structure Communications},
	volume = {67},
	number = {11},
	year = {2011},
	month = {NOV},
	pages = {O435-O438},
	publisher = {WILEY-BLACKWELL},
	address = {COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA},
	abstract = {<p>The conversion of myo-inositol to epi-inositol can be achieved by the hydride reduction of an intermediate epi-inosose derived from myo-inositol. (-)-epi-Inosose, (I), crystallized in the monoclinic space group P2(1), with two independent molecules in the asymmetric unit [Hosomi et al. (2000). Acta Cryst. C56, e584-e585]. On the other hand, (2RS,3SR,5SR,6SR)epi-inosose, C6H10O6, (II), crystallized in the orthorhombic space group Pca2(1). Interestingly, the conformation of the molecules in the two structures is nearly the same, the only difference being the orientation of the C-3 and C-4 hydroxy H atoms. As a result, the molecular organization achieved mainly through strong O-H center dot center dot center dot O hydrogen bonding in the racemic and homochiral lattices is similar. The compound also follows Wallach{\textquoteright}s rule, in that the racemic crystals are denser than the optically active form.</p>},
	issn = {0108-2701},
	doi = {10.1107/S0108270111039412},
	author = {Krishnaswamy, Shobhana and Patil, Madhuri T. and Shashidhar, Mysore S.}
}
@article { ISI:000342609300017,
	title = {Crystal-to-crystal thermal phase transformation of polymorphs of isomeric 2,3-naphthalene diol ditoluates: mechanism and implications for molecular crystal formation and melting},
	journal = {Crystal Growth \& Design},
	volume = {14},
	number = {10},
	year = {2014},
	month = {OCT},
	pages = {4985-4996},
	publisher = {AMER CHEMICAL SOC},
	type = {Article},
	address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA},
	abstract = {<p>Isomeric para- (1) and meta- (2) ditoluate derivatives of naphthalene 2,3-diol exhibited polymorphism producing three (Forms 1I, 1II, 1III) and two (Forms 2I, 2II) polymorphs each, respectively, depending on the solvent and conditions of crystallization. Crystal forms 1I, 1II, and 2I could be obtained repeatedly, whereas crystal forms 1III and 2II were obtained (separately) in one of the crystallization experiments, each. All the crystal forms were stable at ambient conditions, except for Form 2II, which disintegrated to a powder over 45 days. In contrast, the ortho-ditoluate (3) of naphthalene 2,3-diol did not exhibit polymorphism; it yielded fibrous chiral crystals from different solvents/conditions. Crystal structure analysis of all these polymorphs revealed dominance of energetically similar weak intermolecular interactions such as CH center dot center dot center dot O, CH center dot center dot center dot pi, pi center dot center dot center dot pi, and their interplay in molecular aggregation resulting in polymorphic modifications. Differential scanning calorimetry (DSC), hot stage microscopy, single crystal and powder X-ray diffraction measurements revealed crystal-to-crystal thermal transformation of Forms 1I and 1II crystals to Form 1III crystals and Form 2II crystals to Form 2I crystals. The transformation of Form 1I and Form 1II crystals to Form 1III crystals can be viewed as progressive destabilization of the crystal lattice during heating and converting to metastable phase, whereas the conversion of Form 2II to Form 2I crystals can be considered as reorganization of an unstable crystalline phase to a stable crystalline phase. Hence comparative studies of the structure of stable, metastable, or transient crystals and crystal-to-crystal transformations involving these forms could aid in unraveling the process of crystallization.</p>},
	issn = {1528-7483},
	doi = {10.1021/cg5005227},
	author = {Tamboli, Majid I. and Krishnaswamy, Shobhana and Gonnade, Rajesh G. and Shashidhar, Mysore S.}
}
@article {44440,
	title = {Correlation of intermolecular acyl transfer reactivity with noncovalent lattice interactions in molecular crystals: toward prediction of reactivity of organic molecules in the solid state},
	journal = {Journal of Organic Chemistry},
	volume = {83},
	year = {2018},
	month = {APR},
	pages = {3952-3959},
	abstract = {Intermolecular acyl transfer reactivity in several molecular Acyl transfer reactivity can be predicted in solution based crystals was studied, and the outcome of the reactivity was analyzed in the light of structural information obtained from the crystals of the reactants. in solid state Minor changes in the molecular structure resulted in significant variations in the noncovalent interactions and packing of molecules in the crystal lattice, which drastically affected the facility of the intermolecular acyl transfer reactivity in these crystals. Analysis of the reactivity vs crystal structure data revealed dependence of the reactivity on electrophile ... nucleophile interactions and C-H center dot center dot center dot pi interactions between the reacting molecules. The presence of these noncovalent interactions augmented the acyl transfer reactivity, while their absence hindered the reactivity of the molecules in the crystal. The validity of these correlations allows the prediction of intermolecular acyl transfer reactivity in crystals and co-crystals of unknown reactivity. This crystal structure-reactivity correlation parallels the molecular structure-reactivity correlation in solution-state reactions, widely accepted as organic functional group transformations, and sets the stage for the development of a similar approach for reactions in the solid state.},
	doi = {10.1021/acs.joc.8b00293},
	author = {Krishnaswamy, Shobhana and Shashidhar, Mysore S.}
}
@article {47631,
	title = {Construction of two-component chemically reactive supramolecular assemblies-acyl migration reactions in cocrystals of napthalene-2,3-diol and its diesters},
	journal = {ChemPlusChem},
	volume = {86},
	year = {2021},
	month = {AUG},
	pages = {1128-1134},
	type = {Article},
	abstract = {Reactions 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.},
	keywords = {Acylation, domino reactions, intermolecular interactions, reaction in cocrystal, solid-state reactions, X-ray diffraction},
	issn = {2192-6506},
	doi = {10.1002/cplu.202100139},
	author = {Bahadur, Vir and Gonnade, Rajesh G. and Tamboli, I. Majid and Krishnaswamy, Shobhana and Shashidhar, Mysore S.}
}
