Abstract
Within a single family of aryl glycerol ethers and their simplest derivatives, examples of all known types of chiral crystallization, viz., conglomerates, racemic compounds, anomalous racemates and ideal and nonideal solid solutions have been found. A relationship was demonstrated between the crystal packing organization and chirality driven properties of organic substances, such as supramolecular gelation, capacity for enantiomeric enrichment and spontaneous resolution.
References
1.
Chirality – From Weak Bosons to the Alpha-Helix, ed. R. Janoschek, Springer-Verlag, Berlin–Heidelberg, 1991.
2.
Chirality in Natural and Applied Science, eds. W. J. Lough and I. W. Wainer, Blackwell/CRC Press, Oxford, 2003.
3.
4.
V. A. Kizel’, Fizicheskie prichiny dissimetrii zhivykh sistem (Physical Reasons for Dissymmetry of Living Systems), Nauka, Moscow, 1985 (in Russian).
5.
Advances in BioChirality, eds. G. Pályi, C. Zucchi and L. Caglioti, Elsevier, Amsterdam, 1999.
6.
Progress in Biological Chirality, eds. G. Pályi, C. Zucchi and L. Caglioti, Elsevier, Oxford, 2004.
7.
Meierhenrich U.
Advances in Astrobiology and Biogeophysics,
2008
8.
A. Guijarro and M. Yus, The Origin of Chirality in the Molecules of Life. A Revision from Awareness to the Current Theories and Perspectives of this Unsolved Problem, Royal Society of Chemistry, Cambridge, 2008.
9.
10.
Murakami H.
Topics in Current Chemistry,
2006
11.
Ari�ns E.J.
European Journal of Clinical Pharmacology,
1984
12.
De Camp W.H.
Chirality,
1989
13.
Hutt A.J.
Chirality,
1991
14.
Lehmann P.A.
Trends in Pharmacological Sciences,
1986
15.
Nelson W.L., Wennerstrom J.E., Sankar S.R.
Journal of Organic Chemistry,
1977
16.
Theil F., Weidner J., Ballschuh S., Kunath A., Schick H.
Journal of Organic Chemistry,
1994
17.
Salazar L., Bermudez J.L., Ramı́rez C., Llama E.F., Sinisterra J.V.
Tetrahedron Asymmetry,
1999
18.
Egri G., Kolbert A., Bálint J., Fogassy E., Novák L., Poppe L.
Tetrahedron Asymmetry,
1998
19.
Klunder J.M., Ko S.Y., Sharpless K.B.
Journal of Organic Chemistry,
1986
20.
Chen J., Shum W.
Tetrahedron Letters,
1995
21.
Kitaori K., Furukawa Y., Yoshimoto H., Otera J.
Tetrahedron,
1999
22.
10.1016/j.mencom.2012.06.001_bib0020_8
Bredikhina
Zh. Org. Khim,
2002
23.
Bredikhin A.A., Bredikhina Z.A., Lazarev S.N., Savel’ev D.V.
Mendeleev Communications,
2003
24.
Kolb H.C., VanNieuwenhze M.S., Sharpless K.B.
Chemical Reviews,
1994
25.
Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., Jacobsen E.N.
Journal of the American Chemical Society,
2002
26.
10.1016/j.mencom.2012.06.001_bib0020_12
Bredikhin
Nauk., Ser. Khim,
2004
27.
Bredikhin A.A., Bredikhina Z.A., Novikova V.G., Pashagin A.V., Zakharychev D.V., Gubaidullin A.T.
Chirality,
2008
28.
I.V. Melikhov, Fiziko-khimicheskaya evolyutsiya tverdogo veshchestva (Physicochemical Evolution of Solids), Binom, Laboratoriya znanii, Moscow, 2006 (in Russian).
29.
A. G. Stromberg and D. P. Semchenko, Fizicheskaya khimiya (Physical Chemistry), Vysshaya shkola, Moscow, 2001 (in Russian).
30.
I. Prigogine and R. Defay, Chemical Thermodynamics, Longmans Green and Co, London–New York–Toronto, 1954.
31.
The Merck Index, 14th edn., ed. M. J. O’Neil, Merck and Co., Inc., Whitehouse Station, NJ, USA, 2006.
32.
5850, mephenesin.
33.
2178, chlorphenesin.
34.
4555, guaifenesin.
35.
5980, methocarbamol.
36.
9444, timolol.
37.
2396, clopidogrel.
38.
6984, paclobutrazol.
39.
6845, omeprazole.
40.
6228, modafinil.
41.
1192, bevantolol.
42.
7840, propranolol.
43.
1489, bunitrolol.
44.
6264, levomoprolol.
45.
5851, mephenoxalone.
46.
5305, ketoprofen.
47.
Coquerel G., Amabilino D.B.
2009
48.
10.1016/j.mencom.2012.06.001_bib0055_1
Eliel
Stereochemistry of Organic Compounds,
1993
49.
10.1016/j.mencom.2012.06.001_bib0055_2
Eliel
Basic Organic Stereochemistry,
2001
50.
10.1016/j.mencom.2012.06.001_bib0060
Jacques
Enantiomers, Racemates and Resolutions,
1994
51.
Pérez-García L., Amabilino D.B.
Chemical Society Reviews,
2002
52.
Pérez-García L., Amabilino D.B.
Chemical Society Reviews,
2007
53.
Bredikhin A.A., Bredikhina Z.A., Akhatova F.S., Zakharychev D.V., Polyakova E.V.
Tetrahedron Asymmetry,
2009
54.
D.V. Zakharychev, S.N. Lazarev, Z.A. Bredikhina, A.A. Bredikhin, Izv. Akad. Nauk, Ser. Khim., 2006, 225 (Russ. Chem. Bull., Int. Ed., 2006, 55, 230).
55.
Bredikhina Z.A., Konoshenko L.V., Zakharychev D.V., Pashagin A.V., Gubaidullin A.T., Bredikhin A.A.
Mendeleev Communications,
2009
56.
Bredikhin A.A., Bredikhina Z.A., Zakharychev D.V., Konoshenko L.V.
Tetrahedron Asymmetry,
2007
57.
10.1016/j.mencom.2012.06.001_bib0090
Coquerel
Enantiomer,
2000
58.
Li Z.J., Zell M.T., Munson E.J., Grant D.J.
Journal of Pharmaceutical Sciences,
2002
59.
Bredikhin A.A., Zakharychev D.V., Bredikhina Z.A., Gubaidullin A.T., Fayzullin R.R.
CrystEngComm,
2012
60.
Kuhnert-Brandst�tter M., Friedl L.
Microchimica Acta,
1977
61.
Kaemmerer H., Lorenz H., Black S.N., Seidel-Morgenstern A.
Crystal Growth and Design,
2009
62.
10.1016/j.mencom.2012.06.001_bib0110
Brienne
Bull. Soc. Chim. Fr.,
1985
63.
MATSUURA T., KOSHIMA H.
Journal of Photochemistry and Photobiology C: Photochemistry Reviews,
2005
64.
Pidcock E.
Chemical Communications,
2005
65.
Gallis H.E., van Ekeren P.J., van Miltenburg J.C., Oonk H.A.
Thermochimica Acta,
1999
66.
Tabora J.E., Corry J., Osifchin R., Lepore J.V., Davidson O.A., Thien M.P.
Fluid Phase Equilibria,
2007
67.
10.1016/j.mencom.2012.06.001_bib0130_1
Cox
Acta Crystallogr.,
2003
68.
10.1016/j.mencom.2012.06.001_bib0130_2
Białonska
Acta Crystallogr.,
2007
69.
10.1016/j.mencom.2012.06.001_bib0130_3
Białonska
Acta Crystallogr.,
2007
70.
Kostyanovsky R.G., Lyssenko K.A., Lenev D.A., Bronzova I.A.
Tetrahedron Asymmetry,
2002
71.
Chion B., Lajzerowicz J., Bordeaux D., Collet A., Jacques J.
The Journal of Physical Chemistry,
1978
72.
Vogt F.G., Copley R.C., Mueller R.L., Spoors G.P., Cacchio T.N., Carlton R.A., Katrincic L.M., Kennady J.M., Parsons S., Chetina O.V.
Crystal Growth and Design,
2010
73.
de Diego H.L., Bond A.D., Dancer R.J.
Chirality,
2011
74.
Bredikhin A.A., Bredikhina Z.A., Zakharychev D.V., Gubaidullin A.T., Fayzullin R.R.
CrystEngComm,
2012
75.
Bredikhina Z.A., Novikova V.G., Zakharychev D.V., Bredikhin A.A.
Tetrahedron Asymmetry,
2006
76.
Gavezzotti A.
Crystallography Reviews,
1998
77.
Fayos J.
Crystal Growth and Design,
2009
78.
Dunitz J.D., Gavezzotti A.
Chemical Society Reviews,
2009
79.
Day G.M.
Crystallography Reviews,
2011
80.
81.
Yatsenko A.V.
Russian Chemical Reviews,
2005
82.
Neumann M., Leusen F. ., Kendrick J.
Angewandte Chemie - International Edition,
2008
83.
Issa N., Karamertzanis P.G., Welch G.W., Price S.L.
Crystal Growth and Design,
2008
84.
Price S.(.
Accounts of Chemical Research,
2008
85.
Harper J.K., Grant D.M.
Crystal Growth and Design,
2006
86.
Lommerse J.P., Motherwell W.D., Ammon H.L., Dunitz J.D., Gavezzotti A., Hofmann D.W., Leusen F.J., Mooij W.T., Price S.L., Schweizer B., Schmidt M.U., van Eijck B.P., Verwer P., Williams D.E.
Acta Crystallographica Section B Structural Science,
2000
87.
Day G.M., Motherwell W.D.
Crystal Growth and Design,
2006
88.
Brock C.P., Dunitz J.D.
Chemistry of Materials,
1994
89.
Brock C.P., Dunitz J.D.
Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals,
1994
90.
Belsky V.K., Zorkaya O.N., Zorky P.M.
Acta Crystallographica Section A Foundations of Crystallography,
1995
91.
10.1016/j.mencom.2012.06.001_bib0185
Sohncke
Entwicklung einer Theorie der Krystallstruktur,
1879
92.
93.
Levkin P.A., Torbeev V.Y., Lenev D.A., Kostyanovsky R.G.
Topics in Stereochemistry,
2006
94.
Leusen F.J.
Crystal Growth and Design,
2003
95.
Pedone C., Benedetti E.
Acta Crystallographica Section B,
1972
96.
Gervais C., Coquerel G.
Acta Crystallographica Section B Structural Science,
2002
97.
Pauchet M., Gervais C., Courvoisier L., Coquerel G.
Crystal Growth and Design,
2004
98.
S.E. Gibson (nee Thomas), H. Ibrahim, J. W. Steed, J. Am. Chem. Soc., 2002, 124, 5109.
99.
Sarma J.A., Desiraju G.R.
Crystal Growth and Design,
2002
100.
Dey A., Kirchner M.T., Vangala V.R., Desiraju G.R., Mondal R., Howard J.A.
Journal of the American Chemical Society,
2005
101.
Kinbara K., Hashimoto Y., Sukegawa M., Nohira H., Saigo K.
Journal of the American Chemical Society,
1996
102.
Kostyanovsky R.G., Kostyanovsky V.R., Kadorkina G.K., Torbeev V.Y.
Mendeleev Communications,
2000
103.
Bredikhin A.A., Litvinov I.A., Krivolapov D.B., Fattahov B.R., Gubaidullin A.T., Akhatova F.S., Bredikhina Z.A.
Journal of Molecular Structure,
2010
104.
Bredikhin A.A., Gubaidullin A.T., Bredikhina Z.A., Krivolapov D.B., Pashagin A.V., Litvinov I.A.
Journal of Molecular Structure,
2009
105.
Bredikhin A.A., Gubaidullin A.T., Bredikhina Z.A.
Journal of Molecular Structure,
2010
106.
Molecular Gels: Materials with Self-assembled Fibrillar Networks, eds. R. G. Weiss and P. Terech, Springer, Dordrecht, 2006.
107.
Dunn B., Zink J.I.
Accounts of Chemical Research,
2007
108.
Low Molecular Weight Organic Gelators, Tetrahedron, 2007, 63 (31), special issue.
109.
Malik S., Fujita N., Shinkai S.
2009
110.
Suzuki M., Hanabusa K.
Chemical Society Reviews,
2009
111.
Smith D.K.
Chemical Society Reviews,
2009
112.
Brizard A., Oda R., Huc I.
Topics in Current Chemistry,
2005
113.
Bredikhin A.A., Bredikhina Z.A., Akhatova F.S., Gubaidullin A.T.
Chemical Communications,
2010
114.
Bredikhin A.A., Bredikhina Z.A., Pashagin A.V.
Mendeleev Communications,
2011
115.
Bredikhin A.A., Bredikhina Z.A., Zakharychev D.V., Pashagin A.V.
Tetrahedron Asymmetry,
2007
116.
R.A. Johnson, K.B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, New York, 1993, pp. 103-158.
117.
10.1016/j.mencom.2012.06.001_bib0265_2
Katsuki
Org. React.,
1996
118.
Wang Z., Zhang X., Sharpless K.B.
Tetrahedron Letters,
1993
119.
Larrow J.F., Jacobsen E.N.
Topics in Organometallic Chemistry
120.
Ready J.M., Jacobsen E.N.
Journal of the American Chemical Society,
1999
121.
10.1016/j.mencom.2012.06.001_bib0280_1
Mullin
Crystallization,
2001
122.
10.1016/j.mencom.2012.06.001_bib0280_2
Tung
Crystallization of Organic Compounds. An Industrial Perspectives,
2009
123.
Chen A.M., Wang Y., Wenslow R.M.
Organic Process Research and Development,
2008
124.
Wang Y., Chen A.M.
Organic Process Research and Development,
2008
125.
Wang Y., LoBrutto R., Wenslow R.W., Santos I.
Organic Process Research and Development,
2005
126.
10.1016/j.mencom.2012.06.001_bib0295
Angew. Chem. Int.,
2006
127.
Lorenz H., Seidel-Morgenstern A.
Thermochimica Acta,
2002
128.
Lorenz H., Seidel-Morgenstern A.
Thermochimica Acta,
2004
129.
Hong Lu Y., Bun Ching C.
Chirality,
2004
130.
Noorduin W., Vlieg E., Kellogg R., Kaptein B.
Angewandte Chemie - International Edition,
2009
131.
van der Meijden M.W., Leeman M., Gelens E., Noorduin W.L., Meekes H., van Enckevort W.J., Kaptein B., Vlieg E., Kellogg R.M.
Organic Process Research and Development,
2009
132.
Levilain G., Rougeot C., Guillen F., Plaquevent J., Coquerel G.
Tetrahedron Asymmetry,
2009
133.
134.
Noorduin W.L., Izumi T., Millemaggi A., Leeman M., Meekes H., Van Enckevort W.J., Kellogg R.M., Kaptein B., Vlieg E., Blackmond D.G.
Journal of the American Chemical Society,
2008
135.
Viedma C., Ortiz J.E., Torres T.D., Izumi T., Blackmond D.G.
Journal of the American Chemical Society,
2008
136.
D. Gernez, Compt. Rend. Acad. Sci., 1866, 63, 843.
137.
138.
Secor R.M.
Chemical Reviews,
1963
139.
Collet A., Brienne M.J., Jacques J.
Chemical Reviews,
1980
140.
10.1016/j.mencom.2012.06.001_bib0345_1
Coquerel
Top. Curr. Chem.,
2007
141.
Levilain G., Coquerel G.
CrystEngComm,
2010
142.
Crosby, Tetrahedron, 1991, 47, 4789.
143.
10.1016/j.mencom.2012.06.001_bib0355
Bredikhina
Tetrahedron: Asymmetry,
2008
144.
A.A. Bredikhin, Z.A. Bredikhina, S.N. Lazarev, O.G. Sinyashin, RF Patent, 2213724, 2003.
145.
Bredikhin A.A., Bredikhina Z.A., Zakharychev D.V., Akhatova F.S., Krivolapov D.B., Litvinov I.A.
Mendeleev Communications,
2006
146.
Bredikhin A.A., Strunskaya E.I., Zakharychev D.V., Krivolapov D.B., Litvinov I.A., Bredikhina Z.A.
Tetrahedron Asymmetry,
2005
147.
Neau S.H., Shinwari M.K., Hellmuth E.W.
International Journal of Pharmaceutics,
1993
148.
Bredikhina Z.A., Zakharychev D.V., Gubaidullin A.T., Bredikhin A.A.
Journal of Molecular Structure,
2009
149.
150.
BARRETT A.M., CULLUM V.A.
British Journal of Pharmacology,
1968
151.
Goodwin G.M., Green A.R.
British Journal of Pharmacology,
1985
152.
Stoschitzky K., Lindner W., Kiowski W.
Journal of Cardiovascular Pharmacology,
2006
153.
Bredikhin A.A., Savel"ev D.V., Bredikhina Z.A., Gubaidullin A.T., Litvinov I.A.
Russian Chemical Bulletin,
2003
154.
Polenske D., Lorenz H., Seidel‐Morgenstern A.
Journal of Pharmaceutical Sciences,
2010
155.
Bredikhin A.A., Bredikhina Z.A., Gubaidullin A.T., Krivolapov D.B., Litvinov I.A.
Mendeleev Communications,
2004
156.
A.A. Bredikhin, Z.A. Bredikhina, S.A. Dieva, O.G. Sinyashin, RF Patent, 2245868, 2005.
157.
A.A. Bredikhin, Z.A. Bredikhina, V.G. Novikova, A.V. Pashagin, O.G. Sinyashin, RF Patent, 2396247, 2010.
158.
Bredikhina Z.A., Novikova V.G., Efremov Y.Y., Sharafutdinova D.R., Bredikhin A.A.
Russian Chemical Bulletin,
2008
159.
Bredikhina Z.A., Eliseenkova R.M., Fayzullin R.R., Novikova V.G., Kharlamov S.V., Sharafutdinova D.R., Latypov S.K., Bredikhin A.A.
Arkivoc,
2011
160.
10.1016/j.mencom.2012.06.001_bib0425
Klussmann
Chem. Commun.,
2007
161.
Lorenz H., Polenske D., Seidel-Morgenstern A.
Chirality,
2006
162.
Polenske D., Lorenz H., Seidel-Morgenstern A.
Crystal Growth and Design,
2007