Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
Tóm tắt
A crystal of an organic compound is the ultimate supermolecule, and its assembly, governed by chemical and geometrical factors, from individual molecules is the perfect example of solid‐state molecular recognition. Implicit in the supramolecular description of a crystal structure is the fact that molecules in a crystal are held together by noncovalent interactions. The need for rational approaches towards solid‐state structures of fundamental and practical importance has led to the emergence of crystal engineering, which seeks to understand intermolecular interactions and recognition phenomena in the context of crystal packing. The aim of crystal engineering is to establish reliable connections between molecular and supramolecular structure on the basis of intermolecular interactions. Ideally one would like to identify substructural units in a target supermolecule that can be assembled from logically chosen precursor molecules. Indeed, crystal engineering
Từ khóa
Tài liệu tham khảo
Vögtle F., 1991, Supramolecular Chemistry: An Introduction
Wells A. F., 1975, Structural Inorganic Chemistry
Desiraju G. R., 1989, Crystal Engineering: The Design of Organic Solids
Corey E. J., 1989, The Logic of Chemical Synthesis
2‐Methoxy‐1 4‐benzoquinone:E. M. D.Keegstra A. L.Spek J. W.Zwikker L. W.Jenneskens J. Chem. Soc. Chem. Commun.1994 1633; 1 4‐dicyanobenzene:
Kitaigorodskii A. I., 1973, Molecular Crystals and Molecules
Zorkii P. M., 1994, Russ. J. Phys. Chem. Engl. Transl., 68, 870
Lehninger A. L., 1993, Principles of Biochemistry, 160
Glusker J. P., 1994, Crystal Structure Analysis for Chemists and Biologists
V. R.Pedireddi J. A. R. P.Sarma G. R.Desiraju J. Chem. Soc. Perkin Trans. 21992 311;
Desiraju G. R., 1993, Acta Chim. Hung., 130, 451
4‐Iodobenzoic acid might just as effectively be used in such a strategy;B. S.Goud V. R.Thalladi V. J.Hoy F. H.Allen J. A. K.Howard G. R.Desiraju unpublished results.
F. H.Allen B. S.Goud V. J.Hoy J. A. K.Howard G. R.Desiraju J. Chem. Soc. Chem. Commun.1994 2729.
C. V. K.Sharma G. R.Desiraju J. Chem. Soc. Perkin Trans. 21994 2345.
V. R.Pedireddi D. S.Reddy B. S.Goud D. C.Craig A. D.Rae G. R.Desiraju J. Chem. Soc. Perkin Trans. 21994 2353.
For recent reports on the use of cyano ⃛ chloro and aza ⃛ chloro interactions in structural design see respectively D. S.Reddy K.Panneerselvam T.Pilati G. R.Desiraju J. Chem. Soc. Chem. Commun.1993 661and
G. R.Desiraju C. V. K.Sharma J. Chem. Soc. Chem. Commun.1991 1239.
C. V. K.Sharma K.Panneerselvam T.Pilati G. R.Desiraju J. Chem. Soc. Perkin Trans. 21993 2209.
J.‐M.Lehn M.Mascal A.DeCian J.Fischer J. Chem. Soc. Perkin Trans. 21992 461.
I. G.Dancein [9].
K.Biradha C. V. K.Sharma K.Panneerselvam L.Shimoni H. L.Carrell D. E.Zacharias G. R.Desiraju J. Chem. Soc. Chem. Commun.1993 1473.
Hung C.‐Y., 1993, J. Am. Chem. Soc., 115, 12602
O.Ermer A.Eling J. Chem. Soc. Perkin Trans. 21994 925; the relationship between organic and inorganic crystal chemistry is lucidly demonstrated here.
Hassel O., 1961, Tidsskr. Kjemi Bergves. Metoll, 21, 60
Foster R., 1969, Organic Charge Transfer Complexes, 299
V. R.Thalladi K.Panneerselvam C. J.Carrell H. L.Carrell G. R.Desiraju J. Chem. Soc. Chem. Commun.1995 341.
Interestingly the trinitrobenzene layers are held together by O ⃛O van der Waals interactions without CH ⃛ O hydrogen bonds. See Ref. [27] p. 14.
M. R.Bryce L. C.Murphy Nature (London)1984 309 119; Ref.[16] contains an update on the literature on crystal engineering of TTF‐TCNQ type materials.
Karfunkel H. R., 1992, Speedup, 6, 43
1993, Acta Chim. Hung., 130, 151
However it is important to note that van der Waals contacts of the type N ⃛ N and O ⃛ O are just as feasible: see for example Ref.[27 76].
For an interesting report on a hydrogen‐bonded complex that may be sublimed intact seeD. R.Armstrong S.Bennett M. G.Davidson R.Snaith D.Stalke D. S.Wright J. Chem. Soc. Chem. Commun.1992 262.
J. Chem. Soc. Chem. Commun.1990 454.