Structure of 4-iodo-trans-cinnamic acid and a study of carboxyl group disorder

Goud, Bruno; Pathaneni, S. S.; Desiraju, Gautam R.

doi:10.1107/s0108270192011168

Cited by 5 publications

(5 citation statements)

References 14 publications

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“…As suggested long ago, 11 the head-to-head packing is consistent with the formation of β-truxinic acid 1 upon UV-irradiation and differs from the head-to-tail arrangement 11 found in R-cinnamic acid (Figure 2). The structure and cell constants are closely related to those reported for 4-chlorocinnamic acid, 33 4-iodocinnamic acid, 34 and 4-formylcinnamic acid 35 (Table 3). For the latter three structures, the short (≈4 Å) axis corresponds to b, a, and a, respectively.…”

Section: Resultssupporting

confidence: 74%

Polymorphism of Cinnamic and α-Truxillic Acids: New Additions to an Old Story

Abdelmoty

Buchholz

et al. 2005

Crystal Growth & Design

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X-ray structure determinations have been carried out and analyzed for two conformational polymorphs of α-truxillic acid (2). Polymorph I (cell parameters known since 1959) is isolated upon recrystallization of 2 from acetic acid−petroleum ether solution, while polymorph II (fully characterized in 1993) is the product of a one-phase solid-state reaction of tail-irradiated α-cinnamic acid. For polymorph II, two redeterminations of mixed crystals containing solid solutions of α-cinnamic acid and 2 (68.1 and 89.5%, respectively) were performed. Analysis of the structural parameters of the 1993 and present redeterminations of the polymorph II structures, as well as comparison to data from the Cambridge Structural Database, confirm that claims of errors in the 1993 structure determination of polymorph II are unfounded. X-ray quality crystals of the β-polymorph of trans-cinnamic acid (cell parameters known since 1964) have been obtained from Et2O/petroleum ether solutions; the crystal structure is quite similar to that of 4-chlorocinnamic acid.

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Section: Resultssupporting

confidence: 74%

Polymorphism of Cinnamic and α-Truxillic Acids: New Additions to an Old Story

Abdelmoty

Buchholz

et al. 2005

Crystal Growth & Design

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“…4-Bromo-1-cubanecarboxylic acid ( 11 ) (Figure ) and 4-iodo-1-cubanecarboxylic acid ( 12 ) (Table ) are isostructural and also adopt the catemer structure 6 , but here, the carboxylic acid groups are disordered (Table ) . Since the CO and the C−OH groups are now indistinguishable, 17 and 18 merge into a single pattern.…”

Section: Resultsmentioning

confidence: 99%

“…Cubanecarboxylic acid 14 adopts the normal dimer 3 . The CO 2 H group is disordered, and there are two molecules, A and B, in the asymmetric unit (Figure ). Unusually, the dimers are of the A···B type (O···O: 2.614, 2.645 Å, Table ).…”

Section: Resultsmentioning

confidence: 99%

Cubanecarboxylic Acids. Crystal Engineering Considerations and the Role of C−H···O Hydrogen Bonds in Determining O−H···O Networks

et al. 1999

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A family of 4-substituted-1-cubanecarboxylic acids have been synthesized and their X-ray crystal structures analyzed. The rare syn-anti O−H···O catemer 6 is a recurring pattern in this series of compounds. Catemer 6 is observed in the crystal structures of 4-chloro-1-cubanecarboxylic acid (10), 4-bromo-1-cubanecarboxylic acid (11), 4-iodo-1-cubanecarboxylic acid (12), and 4-(methoxycarbonyl)-1-cubanecarboxylic acid (13). The ready occurrence of catemer 6 in this family is ascribed to its stabilization by auxiliary C−H···O hydrogen bonds formed by the relatively acidic cubyl C−H groups. The frequency of occurrence of 6 also facilitates its definition as a useful supramolecular synthon. As is true in many catemers, the formation of 6 is sensitive to steric factors. Therefore, the robustness of this synthon may be assessed by analyzing the crystal structures of molecules wherein the 4-substituent is too small (R = H, 14), too large (R = Ph, 15), or has a specific hydrogen bonding preference of its own (R = CONH2, 16). In these structures, either dimer 3 (in 14 and 15) or heterodimer 22 (in 16) is observed. Powder diffraction shows that the previously noted structure of 1,4-cubanedicarboxylic acid (7) that contains catemer 6 is characteristic of the bulk material. In summary, the syn-anti catemer is the dominant supramolecular synthon in this family of cubanecarboxylic acids.

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“…The angle between the mean plane of the benzene ring and the mean plane of the propenoic acid moiety is 3.5 (7) in (I) and 2.6 in 4-dimethylamino-3-nitrocinnamic acid (Huber, 1985). The corresponding angles in 4-chlorocinnamic acid (Glusker et al, 1975), 4-iodocinnamic acid (Goud et al, 1993), p-nitrocinnamic acid (Kageyama et al, 1993), 3,5-dinitrocinnamic acid and the 3,5-dinitrocinnamic acid 2,5dimethoxycinnamic acid complex (Desiraju & Sharma, 1991) are 14.1, 13.8, 4.7, 28.7 and 6.4 , respectively. In the 3,5dinitrocinnamic acid 4-(N,N-dimethylamino)cinnamic acid complex, the propenoic acid group is twisted by 7.6 out of the mean plane of the benzene ring (Sharma et al, 1993).…”

Section: Commentmentioning

confidence: 98%

3-Nitrocinnamic acid

et al. 2005

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Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.003 Å R factor = 0.046 wR factor = 0.146 Data-to-parameter ratio = 11.5For details of how these key indicators were automatically derived from the article, see A view of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. organic papers Acta Cryst. (2005). E61, o3636-o3638 Udaya lakshmi et al. C 9 H 7 NO 4 o3637

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Structure of 4-iodo-trans-cinnamic acid and a study of carboxyl group disorder

Cited by 5 publications

References 14 publications

Polymorphism of Cinnamic and α-Truxillic Acids: New Additions to an Old Story

Polymorphism of Cinnamic and α-Truxillic Acids: New Additions to an Old Story

Cubanecarboxylic Acids. Crystal Engineering Considerations and the Role of C−H···O Hydrogen Bonds in Determining O−H···O Networks

3-Nitrocinnamic acid

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