Abstract
This review focuses on structural aspects of inclusion complexation between selected host molecules that contain - OH sensor groups appended to, or associated with, heterocyclic moieties, and both non-chiral and chiral guests. Among the host compounds discussed, those derived from tartaric acid feature prominently as they have been extensively explored, especially in the context of optical resolution of racemic guests. Of the various techniques employed in the study of the derived solid-state inclusion complexes, single crystal X-ray studies have contributed significantly to an understanding of the roles of hydrogen bonding, van der Waals, C-H···π and π-π interactions in complex stabilization. For the host molecules described, the literature surveyed accordingly provides many case studies that feature X-ray analysis as a primary tool for investigating the mechanistic aspects of inclusion phenomena such as optical resolution and enantioselective photoreactivity.
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Abbreviations
- ATR:
-
Attenuated total reflection
- CD:
-
Circular dichroism
- DSC:
-
Differential scanning calorimetry
- EIC:
-
Enantioselective inclusion complexation
- GC:
-
Gas chromatography
- HPLC:
-
High performance liquid chromatography
- OSN:
-
Organic solvent nanofiltration
- PXRD:
-
Powder X-ray diffraction
- SSNMR:
-
Solid-state nuclear magnetic resonance
- TADDOL:
-
α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5-dimethanol
- TGA:
-
Thermogravimetric analysis
References
Toda F (1996) Diol, bisphenol, and diamide host compounds. In: McNicol D D, Toda F, Bishop R (eds) Comprehensive supramolecular chemistry, chap 15, vol 6. Oxford, Pergamon, pp 465–516
Seebach D, Beck AK, Heckel A (2001) Angew Chem Int Ed 40:92–138
Seebach D, Hungerbühler E (1980) In: Scheffold E (ed) Modern synthetic methods, vol 2. Salle, Saüerlander, pp 91–171
Toda F, Tanaka K (1988) Tetrahedron Lett 29:551–554
Weber E, Dörpinghaus N, Goldberg I (1988) J Chem Soc Chem Comm 1566–1568
Nassimbeni LR, Niven ML, Tanaka K, Toda F (1991) J Chem Crystallogr 21:451–457
Vinogradov MG, Kurilov DV, Chel’tsova GV, Ferapontov VA, Heise GL (2003) Mendeleev Commun 13:124–125
Novák T, Schindler J, Ujj V, Czugler M, Fogassy E, Keglevich G (2006) Tetrahedron Asymmetry 17:2599–2602
Kaupp G (1994) Angew Chem Int Ed Engl 33:728–729
Toda F, Takumi H (1996) Enantiomer 1:29–33
Ghazali NF, Ferreira FC, White AJP, Livingston AG (2006) Tetrahedron Asymmetry 17:1846–1852
Gajda J, Jeziorna A, Ciesielski W, Potrzebowski WM, Prezdo WW, Potrzebowski MJ (2007) Solid State Nucl Magn Reson 31:153–161
Hirano S, Toyota S, Toda F (2004) Chem Commun 2354–2355
Hirano S, Toyota S, Kato M, Toda F (2005) Chem Commun 3646–3648
Kato M, Tanaka K, Toda F (2001) Supramol Chem 13:175–180
Boese R, Antipin MY, Blaeser D, Lyssenko KA (1998) J Phys Chem B 102:8654
Urbanczyk-Lipkowska Z, Yoshizawa K, Toyota S, Toda F (2003) CrystEngComm 5:114–116
Olszewska T, Milewska MJ, Gdaniec M, Małuszyńska H, Połoński T (2001) J Org Chem 66:501–506
Olszewska T, Pyszno A, Milewska MJ, Gdaniec M, Połoński T (2005) Tetrahedron Asymmetry 16:3711–3717
Tsunoda T, Kaku H, Nagaku M, Okuyama E (1997) Tetrahedron Lett 38:7759–7760
Kaku H, Ozako S, Kawamura S, Takatsu S, Ishii M, Tsunoda T (2001) Heterocycles 55:847–850
Kaku H, Takaoka S, Tsunoda T (2002) Tetrahedron 58:3401–3407
Novák T, Ujj V, Schindler J, Czugler M, Kubinyi M, Mayer ZA, Fogassy E, Keglevich G (2007) Tetrahedron Asymmetry 18:2965–2972
Tanaka K, Takenaka H, Caira MR (2006) Tetrahedron Asymmetry 17:2216–2219
Urbanczyk-Lipkowska Z, Fukuda N, Tanaka K (2007) Tetrahedron Asymmetry 18:1254–1256
Tanaka K, Kukichi D, Caira MR (2006) Tetrahedron Asymmetry 17:1678–1683
Tanaka K, Toda F (2000) Chem Rev 100:1025–1074
Hosomi H, Ohba S, Tanaka K, Toda F (2000) J Am Chem Soc 122:1818–1819
Ohba S, Hosomi H, Tanaka K, Miyamoto H, Toda F (2000) Bull Chem Soc Jpn 73:2075
Tanaka K, Nagahiro R, Urbanczyk-Lipkowska Z (2001) Org Lett 3:1567–1569
Tanaka K, Fujiwara, Urbanczyk-Lipkowska Z (2002) Org Lett 4:3255–3257
Tanaka K, Mochizuki E, Yasui N, Kai Y, Miyahara I, Hirotsu K, Toda F (2000) Tetrahedron 56:6853–6865
Tanaka K, Fujiwara T (2005) Org Lett 7:1501–1503
Gerard B, Sangji S, O’Leary D, Porco JA Jr (2006) J Am Chem Soc 128:7754–7755
McGilvra JD, Unni AK, Modi K, Rawal VH (2006) Angew Chem Int Ed 45:6130–6133
Caira MR, Fujiwara T, Tanaka K (2006) Anal Sci 22:x69–x70
Korupoju SR, Zacharias PS (1998) Chem Commun 1267–1268
Paluch M, Lisowski J, Lis T (2006) Dalton Trans 381–388
Müller S, Afraz MC, de Gelder R, Ariaans GJA, Kaptein B, Broxterman QB, Briggink A (2005) Eur J Org Chem 1082–1096
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MRC thanks the University of Cape Town and the National Research Foundation for research support. Any opinion, findings and conclusions or recommendations expressed in this material are those of the authors and therefore the NRF does not accept any liability in regard thereto.
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Caira, M.R., Tanaka, K. (2009). Inclusion and Optical Resolution of Guest Molecules by Selected Synthetic Dihydroxy- and Trihydroxy-Host Compounds Containing Heterocyclic Scaffolds. In: Matsumoto, K., Hayashi, N. (eds) Heterocyclic Supramolecules II. Topics in Heterocyclic Chemistry, vol 18. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_2
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