Organic crystals: Engineering and design

Current Opinion in Solid State and Materials Science

Volumn 1, Issue 4, 1996, Pages 501-505

  Gavezzotti, Angelo ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002723801     PISSN: 13590286     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0286(96)80065-9     Document Type: Article

References (36)

1. Desiraju GR: Supramolecular synthons in crystal engineering - a new organic synthesis. Angew Chem Int Ed 1995, 34:2311-2327. Crystal engineering is defined as aiming to establish reliable connections between molecular and supramolecular (crystal) structure on the basis of intermolecular interactions; as such it is said to be a new organic synthesis, using intermolecular rather than valence interactions. Supramolecular synthons replace molecular synthons for this new task. This paper is likely to have substantial influence on the future of organic chemistry.
2. Gavezzotti A: Statistical analysis of some structural properties of hydrocarbons. J Am Chem Soc 1989, 111:1835-1843.
3. Pirard B, Baudoux G, Durant F: A database study of intermolecular NH...O hydrogen bonds for carboxylates, sulfonates and monohydrogen phosphonates. Acta Crystallogr B-Struct Sci 1995, 51:103-107.
4. Steiner T, Saenger W: Geometric analysis of non-ionic O-H...O hydrogen bonds and non-bonding arrangements in neutron diffraction studies of carbohydrates. Acta Crystallogr B-Struct Sci 1992, 48:819-827.
5. Shimoni L, Glusker JP, Bock CW: Energies and geometries of isographic hydrogen-bonded networks: 1. The R22(8) graph set. J Am Chem Soc 1996, 100:2957-2967.
6. Gilli P, Bertolasi V, Ferretti V, Gilli G: Covalent nature of the strong homonuclear hydrogen bond. Study of the O-H...O system by crystal structure correlation methods. J Am Chem Soc 1994, 116:909-915.
7. Braga D, Grepioni F, Biradha K, Pedireddi VR, Desiraju GR: Hydrogen bonding in organometallic crystals: 2. C-H...O hydrogen bonds in bridged and terminal first-row metal carbonyls. J Am Chem Soc 1995, 117:3156-3166.
8. Burrows AD, Chan CW, Chowdry MM, McGrady JE, Mingos DMP: Multidimensional crystal engineering of bifunctional metal complexes containing complementary triple hydrogen bonds. Chem Soc Rev 1995, 24:329-339.
9. Kolotuchin SV, Fenlon EE, Wilson SR, Loweth CJ, Zimmermann SC: Self-assembly of 1,3,5-benzenetricarboxylic acids (trimesic acids) and several analogues in the solid state. Angew Chem Int Ed 1995, 34:2654-2657.
10. Hunter CA: The role of aromatic interactions in molecular recognition. Chem Soc Rev 1994, 23:101-109.
11. Dahl T: The nature of stacking interactions between organic molecules elucidated by analysis of crystal structures. Acta Chem Scand 1994, 48:95-106.
12. Laatikainen R, Ratilainen J, Sebastian R, Santa H: NMR study of aromatic-aromatic interactions for benzene and some other fundamental aromatic systems using alignment of aromatics in strong magnetic fields. J Am Chem Soc 1995, 117:11006-11010.
13. Tun L, Dannenberg JJ: Molecular orbital study of crystalline acetic acid. 2. Aggregates in one, two and three dimensions. J Am Chem Soc 1994, 116:8714-8721.
14. Suhai S: Structure and bonding in the formamide crystal: a complete fourth-order many-body perturbation theoretical study. J Chem Phys 1995, 103:7030-7039.
15. Novoa JJ, Rovira MC, Rovira C, Veciana J, Tarres J: C-H...S and S...S: two major forces in organic conductors. Adv Mater 1995, 7:233-237.
16. Willock DJ, Price SL, Leslie M, Cattow CRA: The relaxation of molecular crystal structures using a distributed multipole electrostatic model. J Comput Chem 1995, 16:628-647. A method is described for obtaining distributed atomic murtipoles to represent all spherical and nonspherical features in the atomic charge distribution. A computer program (DMAREL) then analytically computes the necessary derivatives of the crystal potential for optimization of the crystal structure. The only restriction concerns the lack of conformational freedom in the constituent molecule. This procedure, computing resources permitting, should ideally be coupled with a systematic structure-generation procedure to perform the final optimizations and produce the appropriate energy ordering, in order to achieve real ab initio crystal structure prediction by energy calculations.
17. Cornell WD, Cieplak P, Bayty CI, Gould IR, Merz KM, Ferguson DM, Spellmeyer DC, Fox T, Caldwell JW, Kollman PA: A second generation force field for the simulation of proteins, nucleic acids, and organic molecules. J Am Chem Soc 1995, 117:5179-5197.
18. MacKerell AD, Wiorkiewicz-Kuczera J, Karplus M: An all-atom empirical energy function for the simulation of nucleic acids. J Am Chem Soc 1995, 117:11946-11975.
19. Gavezzotti A, Filippini G: Geometry of the intermolecular X-H...Y (X,Y=N,O) hydrogen bond and the calibration of empirical hydrogen-bond potentials. J Phys Chem 1994, 98:4831-4837.
20. Gavezzotti A: The polymorphism of 7-dimethylaminocy-clopenta[c]coumarin: packing analysis and generation of trial crystal structures. Acta Crystallogr B-Struct Sci 1996, 52:201-208.
21. Shoda T, Yamahara K, Okazaki K, Williams DE: Molecular packing analysis of benzene crystals II: prediction of experimental crystal polymorphs at low and high pressure. J Mol Struct 1995, 333:267-274.
22. Chaka AM, Zaniewski R, Youngs W, Tessier C, Klopman G: Predicting the crystal structure of organic molecular materials. Acta Crystallogr B-Struct Sci 1996, 52:165-183.
23. -1 were found for each compound even with the restriction of a single space group. The sensitivity of the force field in distinguishing between them was properly discussed.
24. Perlstein J: Molecular self-assemblies: 4. Using Kitaigorodskii's aufbau principle for quantitatively predicting the packing geometry of semiflexible organic molecules in translation monolayer aggregates. J Am Chem Soc 1994, 116:11420-11432.
25. Gibson KD, Scheraga HA: Crystal packing without symmetry constraints: 1. Tests of a new algorithm for determining crystal structures by energy minimization. J Phys Chem 1995, 99:3752-3764.
26. ••] for control of growth from solution).
27. Svishchev IM, Kusalik PG: Electrofreezing of liquid water. A microscopic prospective. J Am Chem Soc 1996, 118:649-654.
28. Weissbuch I, Popovitz-Biro R, Lahav M, Leiserowitz L: Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using 'tailor-made' auxiliaries. Acta Crystallogr B-Struct Sci 1995, 51:115-148. This paper illustrates recent developments in techniques for controlling the formation of organic crystals, using trace inhibitors - chemical substances that selectively block one or several possible molecular docking sites - or template substrates that favor a predictable molecular arrangement in the growing solid. Both inhibitors and templates are designed on the basis of structural match and of steric or electrostatic molecular compatibility. The experimental procedures involved are as clever as they are awkward, but undoubtedly show great promise for future, wider applicability.
29. Gavezzotti A, Filippini G: Polymorphic forms of organic crystals at room conditions: thermodynamic and structural implications. J Am Chem Soc 1995, 117:12299-12305.
30. Bonafede SJ, Ward MD: Selective nucleation and growth of an organic polymorph by ledge-directed epitaxy on a molecular crystal substrate. J Am Chem Soc 1995, 117:7853-7861.
31. Larsen S, Marthi K: Structures of racemic halogen-substituted 3-hydroxy-3-phenylpropionic adds: relations between spontaneously resolved and racemic compounds. Acta Crystallogr B-Struct Sci 1995, 51:338-346.
32. Van der Sluis P, Kroon J: Solvents and X-ray crystallography. J Cryst Growth 1989, 97:645-656.
33. Frenken JWM: Surface melting. Endeavour 1990, 14:2-7.
34. Chin DN, Gordon DM, Whitesides GM: Computational simulations of hydrogen-bonded aggregates: HubM3,FlexM3, and adamantane-based hubs in chloroform. J Am Chem Soc 1994, 116:12033-12044.
35. Benghiat V, Leiserowrtz L: Molecular pecking modes. Part VI. Crystal and molecular structures of two modifications of tetrolic acid. J Chem Soc 1972, 1763-1768.
36. Dunitz JD, Bemstein J: Disappearing polymorphs. Accounts Chem Res 1995, 28:193-200.