Abstract
Studies of cyclodextrin chemistry by quantum chemical methods are briefly surveyed. Emphases are put on what types of quantum chemical methods can be used for cyclodextrin chemistry, how to use quantum chemical methods to find the global minimum, to study the structures, binding energies, driving forces for cyclodextrin complexes, as well as chemical reactions occurring inside cyclodextrin cavities. Problems associated with the application of quantum chemical methods in cyclodextrin chemistry are also discussed.
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W. Saenger J. Jacob K. Gessler T. Steiner S. Daniel H. Sanbe K. Koizumi S.M. Smith T. Takaha (1998) ArticleTitle␣ Chem. Rev. 98 1787
H. Ueda (2002) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 44 53
K.A. Connors (1997) ArticleTitle␣ Chem. Rev. 97 1325
K. Uekama (2002) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 44 3
K. Takahashi (1998) ArticleTitle␣ Chem. Rev. 98 2013
K. Kano H. Hasegawa (2001) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 41 41
(a) H.J. Buschmann, D. Knittel, and E. Schollmeyer: J. Incl. Phenom. Macrocycl. Chem. 40, 169 (2001); (b) S. Monti and S. Sortino: Chem. Soc. Rev. 31, 287 (2002); (c) A. Harada: Acc. Chem. Res. 34, 456 (2001).
(a) R. Breslow and S.D. Dong: Chem. Rev. 98, 1829 (1998); (b) F. Cao, Y. Ren, W.-Y. Hua, K.-F. Ma, and Y.-L. Guo: Chin. J. Org. Chem. 22, 827 (2002).
(a) W. Saenger: Angew. Chem. Int. Ed. Engl. 19, 344 (1980); (b) G. Wenz: Angew. Chem. Int. Ed. Engl. 33, 803 (1994); (c) Y. Liu and C.-C. You: Chin. J. Chem. 19, 533 (2001).
K.B. Lipkowitz (1998) ArticleTitle␣ Chem. Rev. 98 1829
Recent examples: (a) P. Bonnet, C. Jaime, and L. Morin-Allory: J.’Org. Chem. 66, 689 (2001); (b) D.J. Barbiric, R.H. de Rossi, and E.A. Castro: Theochem 537, 235 (2001); (c) M. Oana, A. Tintaru, D. Gavriliu, O. Maior, and M. Hillebrand: J. Phys. Chem. B 106, 257 (2002); (d) I. Pastor, A. Di Marino, and F. Mendicuti: J. Phys. Chem. B 106, 1995 (2002); (e) L. Cunha-Silva and J.J.C. Teixeira-Dias: J. Incl. Phenom. Macrocycl. Chem. 43, 127 (2002).
Recently examples: (a) M.-Y. Nie, L.-M. Zhou, Q.-H. Wang, and D.-Q. Zhu: Acta Chim. Sin. 59, 268 (2001); (b) J. Varady, X. Wu, and S. Wang: J. Phys. Chem. B 106, 4863 (2002); (c) P. Bonnet, C. Jaime, and L. Morin-Allory: J. Org. Chem. 67, 8602 (2002); (d) I. Bea, C. Jaime, and P. Kollman: Theor. Chem. Acc. 108, 286 (2002); (e) L. Lawtrakul, H. Viernstein, and P. Wolschann: Int. J. Pharm. 256, 33 (2003); (f) K.-L. Yin, D.-J. Xu, and C.-L. Chen, Acta Phys. – Chim. Sin. 19, 480 (2003); (g) A. Mele, G. Raffaini, F. Ganazzoli, and A. Selva: J. Incl. Phenom. Macrocycl. Chem. 44, 219 (2002).
J.A. Pople G.A. Segal (1966) ArticleTitle␣ J. Chem. Phys. 44 3289
(a) M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue, and R. Chujo: Carbohydr. Res. 163, C1 (1987); (b) M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue, and R. Chujo: Chem. Lett. 895 (1988); (c) M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue, and R. Chujo: Bull. Chem. Soc. Jpn. 61, 4225 (1988).
(a) M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue, and R. Chujo: Carbohydr. Res. 198, 181 (1990); (b) M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue, and R. Chujo: Bull. Chem. Soc. Jpn. 62, 2067 (1989).
M.J.S. Dewar W. Thiel (1977) ArticleTitle␣ J. Am. Chem. Soc. 99 4899
M.J.S. Dewar E.G. Zoebisch E.F. Healy J.J.P. Stewart (1985) ArticleTitle␣ J. Am. Chem. Soc. 107 3902
J.J.P. Stewart (1989) ArticleTitle␣ J. Comput. Chem. 10 209
N.T. Anh G. Frisson A. Solladie-Cavallo P. Metzner (1998) ArticleTitle. Tetrahedron 54 12841
First reports of using AM1 to study CDs: (a) V.B. Luzhkov and C.A. Venanzi: J. Phys. Chem. 99, 2312 (1995); (b) N.S. Bodor, M.-J. Huang, and J.D. Watts: J. Pharm. Sci. 84, 330 (1995).
First report of using PM3 to study CDs: C. Margheritis and C. Sinistri: Z. Naturforschung A 51, 950 (1996).
(a) V.G. Avakyan, V.B. Nazarov, M.V. Alfimov, and A.A. Bagatur’yants: Russ. Chem. Bull. 48, 1833 (1999); (b) V.G. Avakyan, V.B. Nazarov, M.V. Alfimov, A.A. Bagatur’yants, and N.I. Voronezheva: Russ. Chem. Bull. 50, 206 (2001).
X.-S. Li L. Liu T.-W. Mu Q.-X. Guo (2000) ArticleTitle␣ Monatsh. Chem. 131 849
L Liu X.S. Li Q.X. Guo Y.C. Liu (1999) ArticleTitle␣ Chin. Chem. Lett. 10 1053
A. Botsi K. Yannakopoulou E. Hadjoudis J. Waite (1996) ArticleTitle␣ Carbohydr. Res. 283 1
N. Bodor M.-J. Huang J.D. Watts (1996) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 25 97
L.A. Godinez B.G. Schulze-Fiehn S. Patel C.M. Criss J.D. Evanseck A.E. Kaifer (1996) ArticleTitle␣ Supramol. Chem. 8 17
M.-J. Huang J.D. Watts N. Bodor (1997) ArticleTitle␣ Int. J. Quantum. Chem. 64 711
M.-J. Huang J.D. Watts N. Bodor (1997) ArticleTitle␣ Int. J. Quantum. Chem. 65 1135
M. Maafi J.J. Aaron C. Lion (1998) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 30 227
X.-S. Li U.L. L.i. Q.-X. Guo S.-D. Chu Y.-C. Liu (1999) ArticleTitle␣ Chem. Phys. Lett. 307 117
L. Liu X.-S. Li K.-S. Song Q.-X. Guo (2000) ArticleTitle␣ Theochem. 531 127
E. Estrada I. Perdomo-Lopez J.J. Torres-Labandeira (2000) ArticleTitle␣ J. Org. Chem. 65 8510
N.B. Boukamel A. Krallafa D. Bormann L. Caron M. Canipelle S. Tilloy E. Monflier (2002) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 42 269
J.W. Minns A. Khan (2002) ArticleTitle. J. Phys. Chem. A 106 6421
N. Bodor P. Buchwald (2002) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 44 9
Y. Fu L. Liu Q.-X. Guo (2002) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 43 223
H.F. Dos Santos H.A. Duarte R.D. Sinisterra S.V. DeMelo Mattos L.F.C. Oliveira ParticleDe W.B. Almeida ParticleDe (2000) ArticleTitle␣ Chem. Phys. Lett. 319 569
L. Liu X.-S. Li Q.-X. Guo (2000) ArticleTitle␣ Theochem. 530 31
M. Shibakami A. Sekiya (1992) ArticleTitle␣ J. Chem. Soc., Chem. Commun. ␣ 1742
J.L. Alderfer A.V. Eliseev (1997) ArticleTitle␣ J. Org. Chem. 62 8225
(a) M. Barra, C. Bohne, and J.C. Scaiano: J. Am. Chem. Soc. 112, 8075 (1990); (b) Y. Liao, J. Frank, J.F. Holzwarth, and C. Bohne: J. Chem. Soc., Chem. Commun. 199, (1995); (c) Y. Liao, J. Frank, J.F. Holzwarth, and C. Bohne: J. Chem. Soc., Chem. Commun. 2435, (1995); (d) R.S. Murphy, T.C. Barros, J. Barnes, B. Mayer, G. Marconi, and C. Bohne: J. Phys. Chem. A 103, 137 (1999); (e) M. Christoff, L.T. Okano, and C. Bohne: J. Photochem. Photobiol. A 134, 169 (2000).
K.-S. Song C.-R. Hou L. Liu X.-S. Li Q.-X. Guo (2001) ArticleTitle␣ J. Photochem. Photobiol. A 139 105
Recent examples: (a) Y. Sueishi, M. Kasahara, and Y. Kotake: Chem. Lett. 792 (2000); (b) D. Takamori, T. Aoki, H. Yashiro, and H. Murai: J. Phys. Chem. A 105, 6001 (2001); (c) Y.-M. Zhang, T.-B. Wei, and X.-X. Peng: Acta Phys. – Chim. Sin. 19, 975 (2003); (d) P. Franchi, M. Lucarini and G.F. Pedulli: Angew. Chem. Int. Ed. 42, 1842 (2003).
(a) W.-G. Li, X.-Q. Ruan, and Q.-X. Guo: Chin. Chem. Lett. 9, 1051 (1998); (b) H.-M. Zhang, X.-Q. Ruan, Q.-X. Guo, and Y.-C. Liu: Chem. Lett. 449 (1998); (c) X.-Q. Zheng, X.-Q. Ruan, W.Wang, H.-M. Zhang, Q.-X. Guo, and Y.-C. Liu: Bull. Chem. Soc. Jpn. 72, 253 (1999); (d) X.-J. Dang, M.-Y. Nie, J. Tong, and H.-L. Li: J. Electroanal. Chem. 437, 53 (1997).
L. Liu X.-S. Li T.-W. Mu Q.-X. Guo Y.-C. Liu (2000) ArticleTitle. J. Incl. Phenom. Macrocycl. Chem. 38 199
T.-W. Mu L. Liu X.-S. Li Q.-X. Guo (2001) ArticleTitle␣ J. Phys. Org. Chem. 14 559
L. Liu K.-S. Song X.-S. Li Q.-X. Guo (2001) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 40 35
L. Liu Q.-X. Guo (2002) ArticleTitle␣ J. Incl. Phenom. Macrocycl. Chem. 42 1
K. Zborowski G. Zuchowski (2002) ArticleTitle␣ Chirality 14 632
V.B. Luzhkov G.A. Venanzi (1995) ArticleTitle␣ J. Phys. Chem. 99 2312
M. Eto S. Kubota H. Nakagawa Y. Yoshitake K. Harano (2000) ArticleTitle␣ Chem. Pharm. Bull. 48 1652
A.M. Granados R.H. Rossi Particlede D.A. Barbiric E.A. Castro (2002) ArticleTitle␣ Theochem. 619 91
(a) J. Tomasi and M. Persico: Chem. Rev. 94, 2027 (1994); (b) C.J. Cramer and D.G. Truhlar: Rev. Comput. Chem. 6, 1 (1995); (c) C.J. Cramer and D.G. Truhlar: Chem. Rev. 99, 2161 (1999).
(a) R. Car and M. Parrinello: Phys. Rev. Lett. 55, 2471 (1985); (b) M.E. Tuckerman: J. Phys. Condens. Matter 14, R1297 (2002).
(a) M.J. Field, P.A. Bash, and M. Karplus: J. Comput. Chem. 11, 700 (1990); (b) J. Aqvist and A. Warshel: Chem. Rev. 93, 2523 (1993); (c) Y.-R. Mo, C. Alhambra, and J.-L. Gao: Acta Chim. Sin. 12, 1504 (2000).
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Liu, L., Guo, QX. Use of Quantum Chemical Methods to Study Cyclodextrin Chemistry. J Incl Phenom Macrocycl Chem 50, 95–103 (2004). https://doi.org/10.1007/s10847-003-8847-3
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DOI: https://doi.org/10.1007/s10847-003-8847-3