Self-assembly of enantiopure 2,2'-dimethylbiphenyl-6,6'-dicarboxylic acid. Formation of chiral squares and their columnar stacking

Tetrahedron Asymmetry

Volumn 10, Issue 17, 1999, Pages 3277-3280

  Tichý, Miloš ^a   Kraus, Tomáš ^a   Závada, Jiří ^a   Císařová, Ivana ^b   Podlaha, Jaroslav ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIMETHYLBIPHENYL 6,6' DICARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; HYDROGEN BOND; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 0033406671     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00367-5     Document Type: Article

References (17)

1. Davies, M. E. Chem. Eur. J. 1997, 3, 1745.
2. Two chiral zeolites are known. However, both of them are polymorphic and retain handedness only over a few crystallographic layers: Newsam, J. M.; Treacy, M. M.; Koitsier, W. T.; de Gruyter, B. Proc. R. Soc. London, Ser. A 1988, 420, 375; Anderson, M. W.; Terasaki, O.; Ohsuna, T.; Philippou, A.; MayKay, S. P.; Ferraira, A.; Rocha, J.; Lidin, S. Nature 1994, 367, 347.
3. Two chiral zeolites are known. However, both of them are polymorphic and retain handedness only over a few crystallographic layers: Newsam, J. M.; Treacy, M. M.; Koitsier, W. T.; de Gruyter, B. Proc. R. Soc. London, Ser. A 1988, 420, 375; Anderson, M. W.; Terasaki, O.; Ohsuna, T.; Philippou, A.; MayKay, S. P.; Ferraira, A.; Rocha, J.; Lidin, S. Nature 1994, 367, 347.
4. Zaworotko, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1211; Kepert, C. J.; Rosseinski, M. J. Chem. Commun. 1998, 31; Stang, P. J. Chem. Eur. J. 1998, 4, 19; Krishnamohan Sharma, C. V.; Rogers, R. G. Chem. Commun. 1999, 83; Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Islar, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949.
5. Zaworotko, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1211; Kepert, C. J.; Rosseinski, M. J. Chem. Commun. 1998, 31; Stang, P. J. Chem. Eur. J. 1998, 4, 19; Krishnamohan Sharma, C. V.; Rogers, R. G. Chem. Commun. 1999, 83; Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Islar, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949.
6. Zaworotko, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1211; Kepert, C. J.; Rosseinski, M. J. Chem. Commun. 1998, 31; Stang, P. J. Chem. Eur. J. 1998, 4, 19; Krishnamohan Sharma, C. V.; Rogers, R. G. Chem. Commun. 1999, 83; Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Islar, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949.
7. Zaworotko, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1211; Kepert, C. J.; Rosseinski, M. J. Chem. Commun. 1998, 31; Stang, P. J. Chem. Eur. J. 1998, 4, 19; Krishnamohan Sharma, C. V.; Rogers, R. G. Chem. Commun. 1999, 83; Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Islar, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949.
8. Zaworotko, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1211; Kepert, C. J.; Rosseinski, M. J. Chem. Commun. 1998, 31; Stang, P. J. Chem. Eur. J. 1998, 4, 19; Krishnamohan Sharma, C. V.; Rogers, R. G. Chem. Commun. 1999, 83; Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Islar, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949.
9. Holý, P.; Závada, J.; Císařová, I.; Podlaha, J. Angew. Chem., Int. Ed. Engl. 1999, 38, 381.
10. A pertinent example of the infinite homochiral network has been recently reported: Vojtíšek, P.; Císařová, I; Podlaha, J.; Žák, Z.; Bohm, S.; Tichý, M.; Závada, J. Z. Kristallogr. 1997, 212, 226.
11. Absolute configuration of the diacid 2a has been determined previously by chemical correlation: McGinn, F. A.; Lazarus, A. K.; Siegel, M.; Ricci, J. E.; Mislow, K. J. Am. Chem. Soc. 1958, 80, 476.
12. 2) was 0.032 for observed data. The atomic coordinates, bond lengths and angles were deposited by CSD and can also be obtained in the form of the CIF file from the author (J.P.) by e-mail: podlaha@natur.cuni.cz.
13. Notably, a comparable tilt of the carboxyl group can be found in the crystal of the enantiopure as well as the racemic (vide infra) diacid 2a, suggesting that it is not related to a particular supramolecular architecture. Conceivably, the tilt stabilizes the intermolecular hydrogen bonds since the acid strength of aromatic carboxylic acids is a function of the out-of-plane angle.
14. 2) was 0.026 for observed data. The atomic coordinates, bond lengths and angles were deposited by CSD and can also be obtained in the form of the CIF file from the author (J.P.) by e-mail.
15. When this study was in progress, the crystal structure of (RS)-2a was independently determined: Gerkin, R. E. Acta Crystallogr. 1998, C54, 1369.
16. The observed self-assembling pattern of the racemic diacid (RS)-2a is unexceptional. According to the Cambridge Database, linking of molecules of opposite chirality into infinite zig-zag chains by double hydrogen bonds is a common feature of racemic 2,2′-disubstituted biaryl-6,6′-dicarboxylic acids.
17. -1.