Aggregate Structures of Carboxylic Acids and Amides

Etter, Margaret C.

doi:10.1002/ijch.198500051

Cited by 40 publications

(11 citation statements)

References 46 publications

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“…Recently, work has been published that refers to both solid solutions and co-crystals contained in one crystalline entity (Chen et al, 2010;Bučar et al, 2012;Oliveira et al, 2008), although for the purposes of this report we will restrict ourselves to describing our complexes as solid solutions. There are many reports on the synthesis of new materials using co-crystallization methods and in particular taking advantage of the hydrogen bonds in the starting materials to derive specific motifs and architectures and can influence the aggregation of different molecules in crystals, sometimes with predictable connectivity patterns (Etter, 1985;Etter et al, 1986;Panunto et al, 1987;Etter & Panunto, 1988;Etter & Baures, 1988;Aakerö y et al, , 2006. In this work, which is focused on solid solutions, we aim to use the predictability of intermolecular interactions to facilitate the process of their formation.…”

Section: Introductionmentioning

confidence: 99%

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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In order to investigate possible isostructural solid solutions of disubstituted N-phenylformamides and thioamides, we have studied the re-crystallization of pairs of compounds selected from 2,6-difluoro-N-phenylformamide (I), 2,6-dichloro-N-phenylformamide (II), 2,6-dimethyl-N-phenylformamide (III), 2,6-dichloro-N-phenylthioamide (IV), 2,6-dimethyl-N-phenylthioamide (V), 2,6-diisopropyl-N-phenylformamide (VI) and 2,6-diisopropyl-N-phenylthioamide (VII). For single-component 2,6-disubstituted-N-phenylformamides only the trans form occurs in the pure crystal, while for thioamides the cis form occurs, with only one exception. By forming solid solutions of pairs of these molecules the resulting structures all adopt similar N-H...O/S chains in the crystals. Solid solutions (1), (2) and (3), resulting from the mixing of (I) and (II), (II) and (III), and (IV) and (V), respectively, are all isostructural with each other (space group Pbca). Only co-crystal (1) is isostructural to both starting materials, while (2) is isostructural to only one of the starting pair, (II). Solid solution (3), which adopts the same Pbca structure as (1) and (2), is different to the monoclinic structures of both the reactants. Solid solution (4) is monoclinic, with similar hydrogen-bonded chains, and isostructural to the two components, resulting from the composition from the mixing of (VI) and (VII). Isostructural indices were used to quantify crystal-packing similarities and differences. Occupancy factors of the reactants in each co-crystal differ widely.

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Section: Introductionmentioning

confidence: 99%

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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“…Particular preference in the development of the strategy for cocrystal formation utilizing hydrogen bonds has traditionally been based on the tendency of carboxylic acids and amides12, 13 to form the homo‐ or heterointermolecular synthons14–16 described in Etter's graph‐set notation17, 18 as an ${{\rm R}{{2\hfill \atop 2\hfill}}}$ (8) ring (which interprets as a ring (R) motif containing eight atoms with two hydrogen‐bond donors (subscript) and two hydrogen‐bond acceptors (superscript); Scheme 1). However, other hydrogen‐bonding motifs such as ${{\rm R}{{2\hfill \atop 1\hfill}}}$ (4) (Scheme 1), have also been investigated 19.…”

Section: Methodsmentioning

confidence: 99%

Designing a Cocrystal of γ‐Amino Butyric Acid

Wenger

Bernstein

2006

Angew Chem Int Ed

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It takes two: The possibility of developing a strategy for the controlled preparation of cocrystals (see picture) with a predesigned structure is demonstrated. It relies on recognizing and utilizing a specific hydrogen‐bond pattern, defined in graph‐set notation (${{{\rm {\rm R}}{{2\hfill \atop 4\hfill}}}}$(8)), as a supramolecular synthon for the systematic generation of individual four‐molecule clusters.

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“…X-ray crystal structural analysis for the cocrystal of oxalic acid/ GABA: Data were collected at 297 K by using a Bruker SMART 6000 CCD diffractometer with Mo Ka radiation (l = 0.71073 ) M r = 98.76, monoclinic space group R2 1 /c, a = 7.4566(9), b = 10.2685 (13), c = 9.7924(12) , b = 108.478(3)8, V = 711.13 (15) 3 , Z = 4, 1 calcd = 1.384 g cm À3 , m(Mo Ka ) = 0.120 mm…”

Section: Methodsmentioning

confidence: 99%

“…Because hydrogen bonds are among the strongest and most preferentially directional intermolecular interactions, they have been the leading candidates for the interactions to be utilized in forming cocrystals, [7][8][9][10] although other interactions have also been suggested. [11a,b] Particular preference in the development of the strategy for cocrystal formation utilizing hydrogen bonds has traditionally been based on the tendency of carboxylic acids and amides [12,13] to form the homo-or heterointermolecular synthons [14][15][16] described in Etters graph-set notation [17,18] as an R 2 2 (8) ring (which interprets as a ring (R) motif containing eight atoms with two hydrogen-bond donors (subscript) and two hydrogen-bond acceptors (superscript); Scheme 1). However, other hydrogen-bonding motifs such as R 2 1 (4) (Scheme 1), have also been investigated.…”

mentioning

confidence: 99%