02591nas a2200241   4500008004100000022001400041245020000055210006900255260007700324300001400401490000700415520160100422653001902023653001302042653002602055653002602081653002402107100001902131700002402150700002302174700002502197856012702222       2005                        eng d  a0947-653900aBenzoyl transfer reactivities of racemic 2,4-Di-O-acyl-myo-inosityl 1,3,5-orthoesters in the solid state: molecular packing and intermolecular interactions correlate with the ease of the reaction0 aBenzoyl transfer reactivities of racemic 24DiOacylmyoinosityl 13  aPO BOX 10 11 61, D-69451 WEINHEIM, GERMANYbWILEY-V C H VERLAG GMBHcMAR  a2103-21100 v113 a<p>Racemic 2,4-di-O-acyl-myoinosityl 1,3,5-orthoesters undergo transesterification catalyzed by sodium carbonate with varying ease of reaction in the solid state; reactions in solution and melt do not show such varied differences. An interesting crystal of a 1:1 molecular complex of highly reactive racemic 2,4-di-O-benzoyl-myo-inosityl 1,3,5-orthoformate and its orthoacetate analogue exhibited better reactivity than the latter component alone. Single-crystal X-ray structures of the reactants have been correlated with the observed differences in the acyl-transfer efficiencies in the solid state. Although each of the derivatives helically self-assembles around the crystallographic 2(1) axis linked through O-(HO)-O-... hydrogen bonding, the pre-organization of the reactive groups (C=O [El] and OH [Nu]), C-(HO)-O-... and the C=H(...)pi interactions are significantly more favourable for the reactive derivatives than the less reactive ones. Bond-length distributions also showed differences; the O-C bond of the axial benzoyl group, which gets cleaved during the reaction, is longer (1.345-1.361 angstrom) relative to the chemically equivalent O-C bond of the equatorial benzoyl group (1.316-1.344 angstrom) in the reactive derivatives. These bond-length differences are not significant in the less reactive derivatives. The overall molecular organization is different too; the strikingly discrete helices, which may be viewed as ``reaction tunnels'' and are held by interhelical interactions, are clearly evident in the reactive derivatives in comparison with the less reactive ones.</p>10ahydrogen bonds10aInositol10asolid-state reactions10astructure elucidation10atransesterification1 aSarmah, M., P.1 aGonnade, Rajesh, G.1 aShashidhar, M., S.1 aBhadbhade, Mohan, M.  uhttps://library.ncl.res.in/content/benzoyl-transfer-reactivities-racemic-24-di-o-acyl-myo-inosityl-135-orthoesters-solid-1