<?xml version="1.0" encoding="UTF-8"?><xml><records><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Shashidhar, Mysore S.</style></author><author><style face="normal" font="default" size="100%">Krishnaswamy, Shobhana</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%"> Intermolecular acyl-transfer reactions in molecular crystals </style></title><secondary-title><style face="normal" font="default" size="100%">Accounts of Chemical Research</style></secondary-title></titles><dates><year><style  face="normal" font="default" size="100%">2019</style></year><pub-dates><date><style  face="normal" font="default" size="100%">FEB</style></date></pub-dates></dates><volume><style face="normal" font="default" size="100%">52</style></volume><pages><style face="normal" font="default" size="100%">437-446</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">&lt;p&gt;CONSPECTUS: It is far more difficult to recognize and predict &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; chemical &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt; that &lt;span class=&quot;hitHilite&quot;&gt;a&lt;/span&gt; molecule &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;an&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;organic&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;compound&lt;/span&gt; can undergo &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; crystalline (solid) state &lt;span class=&quot;hitHilite&quot;&gt;as&lt;/span&gt; compared to &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; solution state (&lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &quot;&lt;span class=&quot;hitHilite&quot;&gt;organic&lt;/span&gt; functional group&quot; approach), since &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; published data on solid-state &lt;span class=&quot;hitHilite&quot;&gt;structure&lt;/span&gt; reactivity investigations and correlations are scant. &lt;span class=&quot;hitHilite&quot;&gt;The&lt;/span&gt; discovery &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; first &lt;span class=&quot;hitHilite&quot;&gt;intermolecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;acyl-transfer&lt;/span&gt; reaction &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; racemic 2,4-di-O-benzoyl-myo-inositol-1,&lt;span class=&quot;hitHilite&quot;&gt;3&lt;/span&gt;,5-orthoformate (DiBz) during our attempts to develop methods &lt;span class=&quot;hitHilite&quot;&gt;for&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;synthesis&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; phosphoinositols, motivated us to find other &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; capable &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; supporting similar &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt;. Small changes to &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;structure&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; DiBz yielded analogues &lt;span class=&quot;hitHilite&quot;&gt;with&lt;/span&gt; different crystal structures which showed varying degrees &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;acyl transfer&lt;/span&gt; reactivity &lt;span class=&quot;hitHilite&quot;&gt;as&lt;/span&gt; compared to &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; DiBz. &lt;span class=&quot;hitHilite&quot;&gt;A&lt;/span&gt; systematic investigation &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; structures, polymorphism, cocrystallization behavior, and &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; corresponding reactivity &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; these &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; allowed us to correlate &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;acyl transfer&lt;/span&gt; reactivity &lt;span class=&quot;hitHilite&quot;&gt;with&lt;/span&gt; their structures and inherent noncovalent interactions and provided crucial insights into &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; mechanism &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; these &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt;. Polymorphs or cocrystals &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; these compounds exhibited dissimilar reactivities due to differences &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; conformation and/or arrangements &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; their &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt;. &lt;span class=&quot;hitHilite&quot;&gt;The&lt;/span&gt; knowledge &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; phase transitions between polymorphs enabled us to control and tune &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; reactivity &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; solid state. We could identify three conditions essential &lt;span class=&quot;hitHilite&quot;&gt;for&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;intermolecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;acyl transfer&lt;/span&gt;: (i) favorable relative geometry &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; electrophile (ester C=O) and &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; nucleophile (OH), (ii) noncovalent interactions (C-H center dot center dot center dot pi) between &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; reacting molecules which help &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; maintaining &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; facility and specificity &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; reaction, and (&lt;span class=&quot;hitHilite&quot;&gt;iii&lt;/span&gt;) &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; presence &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; channels &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; lattice which enable propagation &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; reaction &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; crystal. Based on this supramolecular &lt;span class=&quot;hitHilite&quot;&gt;structure&lt;/span&gt; reactivity correlation, we identified other &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; (composed &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; molecules &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; widely different &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;structure&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;from&lt;/span&gt; that &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; DiBz) &lt;span class=&quot;hitHilite&quot;&gt;from&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;a&lt;/span&gt; survey &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; Cambridge Structural Database (CSD) and predicted their &lt;span class=&quot;hitHilite&quot;&gt;acyl transfer&lt;/span&gt; reactivity. &lt;span class=&quot;hitHilite&quot;&gt;The&lt;/span&gt; increased availability &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; user-friendly modern X-ray diffractometers and related software has enabled &lt;span class=&quot;hitHilite&quot;&gt;efficient&lt;/span&gt; collection, &lt;span class=&quot;hitHilite&quot;&gt;analysis&lt;/span&gt; and interpretation &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; single crystal X-ray diffraction data, essential &lt;span class=&quot;hitHilite&quot;&gt;for&lt;/span&gt; such studies. &lt;span class=&quot;hitHilite&quot;&gt;The&lt;/span&gt; rapidly expanding CSD facilitates &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; identification &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;with&lt;/span&gt; similar structures and reactivity patterns. &lt;span class=&quot;hitHilite&quot;&gt;In&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;a&lt;/span&gt; wider perspective, facile &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; fascinate chemists because these &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt; usually exhibit unique product selectivity and have &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; potential to be developed &lt;span class=&quot;hitHilite&quot;&gt;as&lt;/span&gt; sustainable green &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt;. We are optimistic that similar approaches &lt;span class=&quot;hitHilite&quot;&gt;for&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;study&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; other group &lt;span class=&quot;hitHilite&quot;&gt;transfer&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; would augment and widen &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; scope &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; chemical &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;molecular&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; particular and &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; solid state &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; general. &lt;span class=&quot;hitHilite&quot;&gt;The&lt;/span&gt; ability to predict &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; reactivity &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; molecules &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; their &lt;span class=&quot;hitHilite&quot;&gt;crystals&lt;/span&gt; could find applications &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;organic&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;synthesis&lt;/span&gt;, material science and industry. Realization &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; involvement &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; inositol derivatives &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; cellular processes led to &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; discovery &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; cellular signal transduction mechanisms. &lt;span class=&quot;hitHilite&quot;&gt;The&lt;/span&gt; ability &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; inositol derivatives to support facile &lt;span class=&quot;hitHilite&quot;&gt;acyl-transfer&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; crystalline state might well have opened &lt;span class=&quot;hitHilite&quot;&gt;a&lt;/span&gt; new avenue &lt;span class=&quot;hitHilite&quot;&gt;for&lt;/span&gt; research &lt;span class=&quot;hitHilite&quot;&gt;in&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;the&lt;/span&gt; area &lt;span class=&quot;hitHilite&quot;&gt;of&lt;/span&gt; &lt;span class=&quot;hitHilite&quot;&gt;organic&lt;/span&gt; solid-state &lt;span class=&quot;hitHilite&quot;&gt;reactions&lt;/span&gt;.&lt;/p&gt;
</style></abstract><issue><style face="normal" font="default" size="100%">2</style></issue><work-type><style face="normal" font="default" size="100%">Article</style></work-type><custom3><style face="normal" font="default" size="100%">&lt;p&gt;Foreign&lt;/p&gt;
</style></custom3><custom4><style face="normal" font="default" size="100%">&lt;p&gt;&lt;span class=&quot;LrzXr kno-fv&quot;&gt;21.661&lt;/span&gt;&lt;/p&gt;
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