Molecular structures of 8,8′-dithioureido-2,2′-binaphthalene derivatives and their anions recognition: An ONIOM investigation

Structural Chemistry

Volumn 20, Issue 5, 2009, Pages 767-780

  Piyaauksornsak, Sirichai ^a   Tangthongkul, Totsaporn ^a   Wanbayor, Raina ^a   Wanno, Banchob ^b   Ruangpornvisuti, Vithaya ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b MAHASARAKHAM UNIVERSITY   (Thailand)

Author keywords

8,80 Dithioureido 2,20 binaphthalene; Anions; BSSE; Carboxylate; DFT; Halide; Host guest; ONIOM; Selectivity

Indexed keywords

EID: 70349871358     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-009-9466-4     Document Type: Article

References (38)

1. Kato R, Nishizawa S, Hayashita T, Teramae N (2001) Tetrahedron Lett 42:5053-5056. doi:10.1016/S0040-4039(01)00916-9.
2. Lee DH, Lee KH, Hong J-I (2001) Org Lett 3:5-8. doi:10.1021/ol006690t.
3. Lee DH, Lee HY, Lee KH, Hong J-I (2001) Chem Commun (Camb) 1188-1189. doi:10.1039/b102187g.
4. Lee DH, Lee HY, Hong J-I (2002) Tetrahedron Lett 43:7273-7276. doi:10.1016/S0040-4039(02)01455-7.
5. Jiménez D, Martínez-Máñnez R, Sancenón F, Soto J (2002) Tetrahedron Lett 43:2823-2825. doi:10.1016/S0040-4039(02)00363-5.
6. Piatek P, Jurczak J (2002) Chem Commun (Camb) 20:2450-2451. doi:10.1039/b207335h.
7. Gunnlaugsson T, Davis AP, O'Brien JE, Glynn M (2002) Org Lett 4:2449-2452. doi:10.1021/ol026004l.
8. Fan A, Hong HK, Valiyaveettil S, Vittal JJ (2002) J Supramol Chem 2:247-254. doi:10.1016/S1472-7862(03)00079-0.
9. Baerrigter H, Grave L, Nissink WM, Chrisstoffels LAJ, Vander Maas JH, Verboom W, de Jong F, Reindoudt DN (1998) Org Chem 63:4174-4180. doi:10.1021/jo972127l.
10. Fan E, van Arman SA, Kincaid D, Hamilton AD (1993) J Am Chem Soc 115:369-370. doi:10.1021/ja00054a066.
11. Lee KH, Hong J-I (2000) Tetrahedron Lett 41:6083-6087. doi:10.1016/S0040-4039(00)00966-7.
12. Wanno B, Rakrai W, Keawwangchai S, Morakot N, Morakot N, Nunthaboot N, Ruangpornvisuti V (2009) J Mol Struct THEOCHEM 902:33-40. doi:10.1016/j.theochem.2009.02.010.
13. Ruangpornvisuti V (2004) J Mol Struct THEOCHEM 686:47-55. doi:10.1016/j.theochem.2004.08.007.
14. Wanno B, Sang-aroon W, Tuntulani T, Pulpoka B, Ruangpornvisuti V (2003) J Mol Struct THEOCHEM 629:137-150. doi:10.1016/S0166-1280(03)00135-0.
15. Ruangpornvisuti V (2004) J Mol Struct THEOCHEM 683:103-113. doi:10.1016/j.theochem.2004.06.022.
16. Wanno B, Ruangpornvisuti V (2004) J Mol Struct THEOCHEM 685:57-71. doi:10.1016/j.theochem.2004.06.016.
17. Wanno B, Ruangpornvisuti V (2006) J Mol Struct 787:76-89. doi:10.1016/j.molstruc.2005.11.006.
18. Wanno B, Ruangpornvisuti V (2007) J Mol Model 13:65-77.
19. Kondo S, Nagamine M, Yano Y (2003) Tetrahedron Lett 44:8801-8804. doi:10.1016/j.tetlet.2003.09.207.
20. Kondo S, Sato M (2006) Tetrahedron 62:4844-4850. doi:10.1016/j.tet.2006.03.002.
21. Becke AD (1988) Phys Rev A 38:3098-3100. doi:10.1103/PhysRevA.38.3098.
22. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:385-789.
23. Maseras F, Morokuma K (1995) J Comput Chem 16:1170-1179. doi:10.1002/jcc.540160911.
24. Humbel S, Sieber S, Morokuma K (1996) J Chem Phys 105:1959-1967. doi:10.1063/1.472065.
25. Dewar MJS, Reynolds CH (1986) J Comput Chem 2:140-143. doi:10.1002/jcc.540070206.
26. Stewart JJP (1989) Comput Chem 10:209-220. doi:10.1002/jcc.540100208.
27. Dapprich S, Komaromi I, Byun KS, Morokuma K, Frisch MJ (1999) J Mol Struct THEOCHEM 461:1-21. doi:10.1016/S0166-1280(98)00475-8.
28. Remko M, Walsh OA, Richards WG (2001) J Phys Chem A 105:6926-6931. doi:10.1021/jp010637k.
29. Remko M (2002) J Phys Chem A 106:5005-5010. doi:10.1021/jp020300y.
30. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh, PA.
31. Flükiger P, Lüthi HP, Portmann S, Weber J (2000) MOLEKEL 4.3: Swiss Center for Scientific Computing, Manno (Switzerland).
32. Boys SF, Bernadi F (1970) Mol Phys 19:553-566. doi:10.1080/00268977000101561.
33. Mayer I, Surjan PR (1992) Chem Phys Lett 191:497-499. doi:10.1016/0009-2614(92)85415-7.
34. Turi L, Dannenberg JJ (1993) J Phys Chem 97:2488-2490. doi:10.1021/j100113a002.
35. Simon S, Duran M, Dannenberg JJ (1999) J Phys Chem A 103:1640-1643. doi:10.1021/jp9842188.
36. Hamza A, Vibok A, Halasz GJ, Mayer I (2000) J Mol Struct THEOCHEM 427:501-502.
37. Makowski M, Raczyska ED, Chmurzyski L (2001) J Phys Chem A 105:869-874. doi:10.1021/jp002458t.
38. Long Y, Liu Y, Lei L, Nie L, Yao S (2001) Analyst (Lond) 126:1090-1094. doi:10.1039/b101478l.