Molecular symmetry and the design of molecular solids: The oxalamide functionality as a persistent hydrogen bonding unit

Journal of the American Chemical Society

Volumn 119, Issue 1, 1997, Pages 86-93

  Coe, Seth ^a   Kane, John J ^a   Nguyen, Tam Luong ^a   Toledo, Leticia M ^a   Wininger, Eric ^a   Fowler, Frank W ^a   Lauher, Joseph W ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXALIC ACID DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG STRUCTURE; MOLECULAR DYNAMICS; SOLID;

EID: 0031043017     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961958q     Document Type: Article

References (31)

1. There are many examples of physical properties that depend upon molecular orientation and spacing as well as crystallographic symmetry. Optical properties depend critically upon the relative orientation of molecular dipoles in a crystal. Electronic properties depend upon molecular contacts and spacing. Topochemical reactions depend upon molecular spacing and relative orientations.
2. Many groups are working on this problem. For a recent review see: Lehn, J.-M. Supramolecular Chemistry. Concepts and Perspectives; VCH Verlagsgesellschaft: Weinheim, 1995.
3. (a) Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634.
4. (b) Chang, Y.-L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991-6000.
5. (c) Toledo, L. M.; Lauher, J. W.; Fowler, F. W. Chem. Mater. 1994, 6, 1222-1226.
6. (d) Kane, J. J.; Liao, R. F.; Lauher, J. W.; Fowler , F. W. J. Am. Chem. Soc. 1995, 117, 12003-12004
7. 3b Discrete assemblies lack translation symmetry and are characterized by their point group symmetry. An α-network has one degree of translational symmetry and is characterized by its rod group symmetry. A β-network has two degrees of translational symmetry and is characterized by its layer group symmetry. A γ-network has three degrees of translational symmetry and is characterized by its space group symmetry. Lauher, J. W.; Chang, Y.-L.; Fowler, F. W. Mol. Cryst. Liq. Cryst. 1992, 211, 99-109.
8. Brock, C. P.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1991, 113, 9811-9820.
9. (a) Karle, I. L.; Ranganathan, D.; Sha, K.; Vaish, N. K. Int. J. Peptide Protein Res. 1994, 43, 160-165.
10. (b) Karle, I. L.; Ranganathan, D. Int. J. Peptide Protein Res. 1995, 46, 18-23.
11. (c) Karle, I. L.; Ranganathan, D. Biopolymers 1995, 36, 323-331.
12. Shkol'nikova L. M.; Gasparyan A. V.; Poznyak A. L.; Bel'skii V. K.; Dyatlova N. M. Koord. Khim. 1990, 16, 50-54.
13. In 7u the hydrogen of the carboxylic acid forms a hydrogen bond to the oxygen atom of the urea carbonyl, while the hydrogen atoms of the urea form hydrogen bonds to the acid carbonyl. See ref 3b.
14. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
15. Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1983, 105, 765-767. Leiserowitz, L.; Nader, F. Acta Crystallogr., Sect. B 1977, 33, 2719-2723. Leiserowitz, L. Acta Crystallogr., Sect. B 1976, 32, 775-802.
16. Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1983, 105, 765-767. Leiserowitz, L.; Nader, F. Acta Crystallogr., Sect. B 1977, 33, 2719-2723. Leiserowitz, L. Acta Crystallogr., Sect. B 1976, 32, 775-802.
17. Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1983, 105, 765-767. Leiserowitz, L.; Nader, F. Acta Crystallogr., Sect. B 1977, 33, 2719-2723. Leiserowitz, L. Acta Crystallogr., Sect. B 1976, 32, 775-802.
18. It is interesting to note that in polymorph A of 1o the β-network can be considered to be an assembly of independent α-networks, the α-networks in turn being assemblies of discrete molecules. However, in polymorph B of 1o the β-network is assembled directly from discrete molecules, and there are no symmetry independent α-networks.
19. We have tried the obvious experiment of growing crystals of 3o from solutions with various pH values, but we have seen no evidence of polymorphism.
20. Allen, F. H.; Taylor, R.; Kennard, O. Acc. Chem. Res. 1983, 16, 146-153.
21. Klaska, K. H.; Jarchow, O.; Scham, W.; Widjaja, H.; Voss, J.; Schmalle, H. W. J. Chem. Res. 1980, 104, 1643-1700.
22. Yamaguchi, K.; Matsumura, G.; Haga, N.; Shudo, K. Acta Crystallogr., Sec. C 1992, 48, 558-559.
23. Bhattacharjee, S. K.; Ammon, H. L. Acta Crystallogr., Sec. B 1982, 38, 2503-2505.
24. Chen, R.; Rheingold, A. L.; Brill, T. B. J. Crystallogr. Spectrosc. 1991, 21, 173-177.
25. Fryer, R. I.; Earley, J. V.; Blout, J. F. J. Org. Chem. 1977, 42, 2212-2219.
26. ○. These values are somewhat similar to those found for 1o (polymorph B) as shown in Table 1.
27. Kondo, K.; Murata, K.; Miyoshi, N.; Murai, S.; Sonoda, N. Synthesis 1979, 735-736.
28. McKay, A. F.; Tarlton, E. J.; Petri, S. I.; Steyermark, P. R.; Mosley, M. A. J. Am. Chem. Soc. 1958, 80, 1510-1517.
29. Giesemann, H.; Oertel M. J. Prakt. Chem. 1959, 4(8), 292-297.
30. Hearn, W. R.; Hendry, R. A. J. Am. Chem. Soc. 1957, 79, 5213-5217.
31. Wieland; Hasse, Kurt, Chem. Ber. 1960, 1686-1692.