@article { ISI:000324316300042,
	title = {Identification of molecular crystals capable of undergoing an acyl-transfer reaction based on intermolecular interactions in the crystal lattice},
	journal = {Chemistry-A European Journal},
	volume = {19},
	number = {38},
	year = {2013},
	month = {SEP},
	pages = {12867-12874},
	publisher = {WILEY-V C H VERLAG GMBH},
	address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY},
	abstract = {<p>Investigation of the intermolecular acyl-transfer reactivity in molecular crystals of myo-inositol orthoester derivatives and its correlation with crystal structures enabled us to identify the essential parameters to support efficient acyl-transfer reactions in crystals: 1)the favorable geometry of the nucleophile (OH) and the electrophile (CO) and 2)the molecular assembly, reinforced by CH interactions, which supports a domino-type reaction in crystals. These parameters were used to identify another reactive crystal through a data-mining study of the Cambridge Structural Database. A 2:1 co-crystal of 2,3-naphthalene diol and its di-p-methylbenzoate was selected as a potentially reactive crystal and its reactivity was tested by heating the co-crystals in the presence of solid sodium carbonate. A facile intermolecular p-toluoyl group transfer was observed as predicted. The successful identification of reactive crystals opens up a new method for the detection of molecular crystals capable of exhibiting acyl-transfer reactivity.</p>},
	keywords = {Acylation, domino reactions, intermolecular interactions, solid-state reactions, X-ray diffraction},
	issn = {0947-6539},
	doi = {10.1002/chem.201301058},
	author = {Tamboli, Majid I. and Krishnaswamy, Shobhana and Gonnade, Rajesh G. and Shashidhar, Mysore S.}
}
@article { ISI:000344793700010,
	title = {Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4 {\textquoteleft}-bipyridine cocrystal with their crystal structures},
	journal = {Acta Crystallographica Section C-Structural Chemistry},
	volume = {70},
	number = {11},
	year = {2014},
	month = {NOV},
	pages = {1040+},
	publisher = {WILEY-BLACKWELL},
	type = {Article},
	address = {111 RIVER ST, HOBOKEN 07030-5774, NJ USA},
	abstract = {<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 {\textquoteleft}-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>},
	keywords = {acyl transfer, cocrystal, crystal structure, design of functional solids, helical assembly, hydrogen bonding, myo-inositol, solid-state reactions},
	issn = {0108-2701},
	doi = {10.1107/S2053229614021834},
	author = {Tamboli, Majid I. and Bahadur, Vir and Gonnade, Rajesh G. and Shashidhar, Mysore S.}
}
