Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives ofmyo-Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

2015 ◽  
Vol 21 (39) ◽  
pp. 13676-13682 ◽  
Author(s):  
Majid I. Tamboli ◽  
Mysore S. Shashidhar ◽  
Rajesh G. Gonnade ◽  
Shobhana Krishnaswamy
Keyword(s):  
Solid State ◽  
Intramolecular Cyclization ◽  
Molecular Crystals ◽  
Transfer Reactions ◽  
Group Transfer ◽  
Acyl Group Transfer Reactions

Correlation 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 structures

2014 ◽  
Vol 70 (11) ◽  
pp. 1040-1045 ◽  
Author(s):  
Majid I. Tamboli ◽  
Vir Bahadur ◽  
Rajesh G. Gonnade ◽  
Mysore S. Shashidhar
Keyword(s):  
Solid State ◽  
Self Assembly ◽  
Transfer Reaction ◽  
Acyl Transfer ◽  
Transfer Reactions ◽  
Group Transfer ◽  
Hydrogen Bonding Interactions ◽  
Benzoyl Group ◽  
The Stability ◽  
Group Migration

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·C10H8N2,(1)·BP, inhibits the intermolecular benzoyl-group transfer reaction. In(1), molecules are assembled around the crystallographic twofold screw axis (baxis) to form a helical self-assembly through conventional O—H...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...Nu geometry favourable for the acyl transfer reaction. In the cocrystal(1)·BP, the dibenzoate and bipyridine molecules are arranged alternately through O—H...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.

Reactivity of micelle-forming 1-alkyl-3(1-oximinoethyl)pyridinium bromides in acyl group transfer reactions

2011 ◽  
Vol 47 (1) ◽  
pp. 21-29 ◽  
Author(s):  
M. K. Turovskaya ◽  
I. V. Kapitanov ◽  
I. A. Belousova ◽  
K. K. Tuchinskaya ◽  
A. E. Shumeiko ◽  
...  
Keyword(s):  
Transfer Reactions ◽  
Group Transfer ◽  
Acyl Group Transfer Reactions

O-nucleophilic features of amidoximes in acyl group transfer reactions

2004 ◽  
Vol 40 (11) ◽  
pp. 1617-1629 ◽  
Author(s):  
T. M. Prokop?eva ◽  
Yu. S. Simanenko ◽  
E. A. Karpichev ◽  
V. A. Savelova ◽  
A. F. Popov
Keyword(s):  
Transfer Reactions ◽  
Group Transfer ◽  
Acyl Group Transfer Reactions

Solid state amorphization of organic molecular crystals using a vibrating mill

1995 ◽  
Vol 94 (12) ◽  
pp. 1013-1018 ◽  
Author(s):  
Itaru Tsukushi ◽  
Osamu Yamamuro ◽  
Takasuke Matsuo
Keyword(s):  
Solid State ◽  
Molecular Crystals ◽  
Organic Molecular Crystals ◽  
State Amorphization

Theoretical Investigation of Polymorph- and Coformer-Dependent Photoluminescence in Molecular Crystals

CrystEngComm ◽  
2021 ◽  
Author(s):  
Xibo Feng ◽  
Axel D. Becke ◽  
Erin R. Johnson
Keyword(s):  
Solid State ◽  
Theoretical Investigation ◽  
Molecular Crystals ◽  
Research Interest

Polymorph- and coformer-dependent photoluminescence (PL) are among the variety of novel solid-state PL phenomena recently observed in many molecular crystals. They are of particular research interest due to their direct...

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