Capturing a metastable chiral polymorph of an achiral molecule—hexa-O-benzoyl-myo-inositol

Gonnade, Rajesh G.; Bhadbhade, Mohan M.; Shashidhar, Mysore S.

doi:10.1039/b410051d

Cited by 27 publications

(19 citation statements)

References 14 publications

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“…A more stable achiral polymorph is generated under thermodynamic conditions, its supramolecular structure consisting of centrosymmetric dimers linked by multiple C-H … O interactions. 58 The complexes formed between cobalt(II) and oxydiacetic acid under hydro-or solvo-thermal conditions show either achiral forms or chiral network, respectively, depending on the hydration at the metal centre. 59 The chiral complex can be obtained from the achiral one (which has a higher degree of hydration) by heating under solvothermal conditions.…”

Section: Conglomerate and Racemate In The Balancementioning

confidence: 99%

Spontaneous resolution, whence and whither: from enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supra-molecular polymers and assemblies

2007

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One of the great challenges in stereochemistry is the explanation of why some molecules resolve spontaneously while others do not. In this critical review the recent advances in the creation of chiral systems from achiral and racemic compounds in three-, two- and one-dimensional systems are discussed. There are some groups of molecules in some systems that do tend to display conglomerates, which may suggest that there are enantiophobic and enantiophilic molecules whose assembly is guided by the structural and thermodynamic properties of the systems in question.

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Section: Conglomerate and Racemate In The Balancementioning

confidence: 99%

Spontaneous resolution, whence and whither: from enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supra-molecular polymers and assemblies

2007

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“…In addition, halogen bonding plays a key role in the field of drug design [7,8] and protein-ligand complexation [9,10]. The growing awareness of halogen bonding is evident from the numerous highlights, reviews and perspectives published in the last few years [7,[11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

A 19F NMR study of C–I⋯π halogen bonding

et al. 2011

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“…In the crystallization process, the formation of the 'nuclei' starting with the first interacting pair seems to be critical in deciding the outcome of the polymorph, as exemplified by the two polymorphic forms of hexa-o-benzyl-myo-inositol (Gonnade et al, 2004). This compound crystallizes in both centrosymmetric (space group P1) and noncentrosymmetric (space group P6 1 ) systems.…”

Section: Resultsmentioning

confidence: 99%

The first polymorph in the family of nucleobases: a second form of cytosine

2015

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A new polymorph of cytosine, C4H5N3O, is reported half a century after the report of its first known crystal structure [Barker & Marsh (1964). Acta Cryst. 17, 1581-1587]. Cytosine thus provides the first polymorphic example in the category of parent nucleobases. The new form, denoted (Ib), was observed unexpectedly during an attempt to cocrystallize cytosine with catechol. Form (Ib) crystallizes in the orthorhombic centrosymmetric space group Pccn with two molecules in the asymmetric unit. The previously known form, denoted (Ia), crystallizes in the orthorhombic noncentrosymmetric space group P212121. The cytosine molecule is planar in both forms. Hydrogen-bonding interactions are also similar for both forms. Infinite one-dimensional ribbons composed of cytosine base-pair dimers in R2(2)(8) arrangements are observed in both (Ia) and (Ib). However, the way that the ribbons are packed differs in (Ia) and (Ib). This appears to guide the centrosymmetric versus noncentrosymmetric space-group selection through the formation of an inversion-related motif in polymorph (Ib) and a helical propagation in polymorph (Ia). A few selected polymorphic systems have been gathered from the Cambridge Structural Database to understand possible structural features responsible for achiral molecules adopting centro- and noncentrosymmetric space groups.

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Capturing a metastable chiral polymorph of an achiral molecule—hexa-O-benzoyl-myo-inositol

Abstract: myo-Inositol hexabenzoate having meso configuration produces chiral polymorph (form I) when crystallized rapidly but yields achiral polymorph (form II) when allowed to crystallize slowly; in the mother liquor form I slowly but completely disappears to give form II.

Cited by 27 publications

References 14 publications

Spontaneous resolution, whence and whither: from enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supra-molecular polymers and assemblies

Spontaneous resolution, whence and whither: from enantiomorphic solids to chiral liquid crystals, monolayers and macro- and supra-molecular polymers and assemblies

A 19F NMR study of C–I⋯π halogen bonding

The first polymorph in the family of nucleobases: a second form of cytosine

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