DFT studies of cation binding by β-cyclodextrin

Theoretical Chemistry Accounts

Volumn 130, Issue 4-6, 2011, Pages 939-953

  Stachowicz, Anna ^a   Styrcz, Anna ^a   Korchowiec, Jacek ^a   Modaressi, Ali ^b   Rogalski, Marek ^b  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b UNIVERSITÉ DE LORRAINE   (France)

Author keywords

cyclodextrin; Cation binding; Energy decomposition scheme; Guest host complexes; Natural orbitals for chemical valence

Indexed keywords

EID: 81855213215     PISSN: 1432881X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00214-011-1014-9     Document Type: Article

References (46)

1. Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98: 1743-1753.
2. Loftsson T, Duchene D (2007) Cyclodextrins and their pharmaceutical applications. Int J Pharm 329: 1-11.
3. Juvancz Z, Kendrovics RB, Ivanyi R, Szente L (2008) The role of cyclodextrins in chiral capillary electrophoresis. Electrophoresis 29: 1701-1712.
4. Rekharsky MV, Inoue Y (1998) Complexation thermodynamics of cyclodextrins. Chem Rev 98: 1875-1917.
5. Connors KA (1997) The stability of cyclodextrin complexes in solution. Chem Rev 97: 1325-1357.
6. Liu L, Guo Q-X (2004) Use of quantum chemical methods to study cyclodextrin chemistry. J Incl Phenom Macrocycl Chem 50: 95-103.
7. Britto MAFO, Nascimnento CS Jr, Dos Santos HF (2004) Structural analysis of cyclodextrins: a comparative study of classical and quantum mechanical methods. Quim Nova 27: 882-888.
8. Pinjari RV, Joshi KA, Gejji SP (2007) Theoretical studies on hydrogen bonding, NMR chemical shifts and electron density topography in α, β and γ-cyclodextrin conformers. J Phys Chem A 111: 13583-13589.
9. Heine T, Dos Santos HF, Patchkovskii S, Duarte HA (2007) Structure and dynamics of beta-cyclodextrin in aqueous solution at the density-functional tight binding level. J Phys Chem A 111: 5648-5654.
10. Snor W, Liedl E, Weiss-Greiler P, Karpfen A, Viernstein H, Wolschann P (2007) On the structure of anhydrous beta-cyclodextrin. Chem Phys Lett 441: 159-162.
11. Anconi CPA, Nascimento CS Jr, Fedoce-Lopes J, Dos Santos HF, De Almeida WB (2007) Ab initio calculations on low-energy conformers of alpha-cyclodextrin. J Phys Chem A 111: 12127-12135.
12. Jimenez V, Alderete JB (2008) Hartree-Fock and density functional theory study of alpha-cyclodextrin conformers. J Phys Chem A 112: 678-685.
13. Nascimento CS, Dos Santos HF, De Almeida WB (2004) Theoretical study of the formation of the alpha-cyclodextrin hexahydrate. Chem Phys Lett 397: 422-428.
14. Rizzarelli E, Vecchio G (1999) Metal complexes of functionalized cyclodextrins as enzyme models and chiral receptors. Coord Chem Rev 188: 343-364.
15. Cai Y, Tarr MA, Xu G, Yalcin T, Cole RB (2003) Dication induced stabilization of gas-phase ternary beta-cyclodextrin inclusion complexes observed by electrospray mass spectrometry. J Am Soc Mass Spectrom 14: 449-459.
16. Zhang Y, Xu W (1989) The aldol condensation catalyzed by metal(II)-β-cyclodextrin complexes. Synth Commun 19: 1291-1296.
17. Ziegler T, Rauk A (1977) On the calculation of bonding energies by the Hartree Fock Slater method. I. The transition state method. Theor Chim Acta 46: 1-10.
18. Mitoraj M, Michalak A (2007) Natural orbitals for chemical valence as descriptors of chemical bonding in transition metal complexes. J Mol Model 13: 347-355.
19. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JJ Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision A. 02; Gaussian, Inc, Wallingford. http://www. gaussian. com.
20. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem A 98: 11623-11627.
21. Styrcz A, Mrozek J, Mazur G (2011, in press) A neural-network controlled dynamic evolutionary scheme for global molecular geometry optimization. Int J Appl Math Comput Sci 21(3) (in press).
22. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su S, Windus TL, Dupuis M, Montgomery JA (1993) General atomic and molecular electronic structure system. J Comput Chem 14: 1347-1363.
23. GAMESS v, Jan. 2003 (R2), Iowa State University. http://www. msg. ameslab. gov/gamess/.
24. Mayer I (1985) Bond orders and valences in the SCF theory: a comment. Theor Chim Acta 67: 315-322.
25. Mayer I (1986) Bond orders and valences from ab initio wave functions. Int J Quantum Chem 29: 477-483.
26. Mrozek J, Nalewajski RF, Michalak A (1998) Exploring bonding patterns of molecular systems using quantum mechanical bond multiplicities. Pol J Chem 72: 1779-1791.
27. Nalewajski RF, Mrozek J, Michalak A (1997) Two-electron valence indices from the Kohn-Sham orbitals. Int J Quantum Chem 61: 589-601.
28. Mitoraj MP, Michalak A, Ziegler T (2009) A combined charge and energy decomposition scheme for bond analysis. J Chem Theory Comput 5: 962-975.
29. Te VG, Bickelhaupt FM, Baerends EJ, Fonseca GC, van GSJA, Snijders JG, Ziegler T (2001) Chemistry with ADF. J Comput Chem 22: 931-967.
30. van Lenthe E, Baerends EJ (2003) Optimized Slater-type basis sets for the elements 1-118. J Comput Chem 24: 1142-1156.
31. Humphrey W, Dalke A, Schulten K (1996) VMD-visual molecular dynamics. J Mol Graph 14: 33-38.
32. Zabel V, Saenger W, Mason SA (1986) Topography of cyclodextrin inclusion complexes. Part 23. Neutron diffraction study of the hydrogen bonding in beta-cyclodextrin undecahydrate at 120 K: from dynamic flip-flops to static homodromic chains. J Am Chem Soc 108: 3664-3673.
33. Lindner K, Saenger W (1982) Topography of cyclodextrin complexes. Part XVII. Crystal and molecular structure of cycloheptaamylose dodecahydrate. Carbohydr Res 99: 103-115.
34. Norkus E (2009) Metal ion complexes with native cyclodextrins. An overview. J Incl Phenom Macrocycl Chem 65: 237-248.
35. Stephens PJ, Jalkanen KJ, Kawiecki RW (1990) Theory of vibration rotational strengths-comparison of a priori theory and approximate models. J Am Chem Soc 112: 6518-6529.
36. Szewczyk B, Sokalski WA, Leszczynski J (2002) Optimal methods for calculation of the amount of intermolecular electron transfer. J Chem Phys 117: 6952-6958.
37. Khaliullin RZ, Cobar EA, Lochan RC, Bell AT, Head-Gordon M (2007) Unravelling the origin of intermolecular interactions using absolutely localized molecular orbitals. J Phys Chem A 111: 8753-8765.
38. Korchowiec J, Uchimaru T (2000) New energy partitioning scheme based on the self-consistent charge and configuration method for subsystems: application to water dimer system. J Chem Phys 112: 1623-1633.
39. Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev 88: 899-926.
40. Kitaura K, Morokuma K (1976) A new energy decomposition scheme for molecular interactions within the Hartree-Fock approximation. Int J Quantum Chem 10: 325-340.
41. Stevens WJ, Fink WH (1987) Frozen fragment reduced variational space analysis of hydrogen bonding interactions. Application to the water dimer. Chem Phys Lett 139: 15-22.
42. Korchowiec J, Korchowiec B, Priebe W, Rogalska E (2008) DFT study on the selectivity of complexation of metal cations with a dioxadithia crown ether ligand. J Phys Chem A 112: 13633-13640.
43. Jalkanen KJ, Degtyarenko IM, Nieminen RM, Cao X, Nafie LA, Zhu F, Barron LD (2008) Role of hydration in determining the structure and vibrational spectra of l-alanine and N-acetyl l-alanine N-methylamide in aqueous solution: a combined theoretical and experimental approach. Theor Chem Acc 119: 191-210.
44. Jürgensen VW, Jalkanen KJ (2006) The VA, VCD, Raman and ROA spectra of tri-l-serine in aqueous solution. Phys Biol 3: S63-S79.
45. Eilmes A, Kubisiak P (2010) Relative complexation energies for Li+ ion in solution: molecular level solvation versus polarizable continuum model study. J Phys Chem A 114: 973-979.
46. Jalkanen KJ, Nieminen RM, Frimand K, Bohr J, Bohr H, Wade RC, Tajkhorshid E, Suhai S (2001) A comparison of aqueous solvent models used in the calculation of the Raman and ROA spectra of l-alanine. Chem Phys 265: 125-151.