Investigating organization of molecules that facilitates intermolecular acyl transfer in crystals: reactivity and x-ray structures of O-benzoyl-myo-inositol 1,3,5-orthoesters

TitleInvestigating organization of molecules that facilitates intermolecular acyl transfer in crystals: reactivity and x-ray structures of O-benzoyl-myo-inositol 1,3,5-orthoesters
Publication TypeJournal Article
Year of Publication2007
AuthorsMurali, C, Shashidhar, MS, Gonnade, RG, Bhadbhade, MM
JournalEuropean Journal of Organic Chemsitry
Volume293
Issue1-3
Pagination1153-1159
Date PublishedFEB
Type of ArticleArticle
ISSN0927-7757
KeywordsAOT, CdS-Ag2S, core-shell, Nanoparticles, w/o microemulsion, XPS
Abstract

{Crystal structure analysis of racemic 2,6-di-O-benzoyl-myo-inositol 1,3,5-orthobenzoate reveals helical organization of the molecules, remarkably similar to that observed earlier in crystals of racemic 2,6-di-O-benzoyl-myo-inositol 1,3,5-orthoformate. Both these dibenzoates are isostructural despite the bulkier phenyl substituent in place of hydrogen. The latter compound shows highly facile intermolecular benzoyl transfer reactivity in its crystals and as anticipated from the crystal structure, the orthobenzoate indeed exhibits facile benzoyl transfer reactivity in its crystals. 2-O-Benzoyl-myo-inositol 1,3,5-orthoformate and the corresponding orthobenzoate also undergo transesterification in their crystals, but the specificity of acyl transfer is very low, and the reaction yields a mixture of products. The parameters of helical molecular assembly that facilitates acyl transfer in crystals have been investigated. A comparison of the molecular assemblies and lattice interactions in crystals of all the four compounds with the observed reactivity patterns show that facile acyl transfer reaction is brought about by a modular ``reaction tunnel''

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

1.64

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry