Solid-state supramolecular array through cooperative π-π interactions of 1-(2-methoxyphenyl)-o-carborane

Tetrahedron

Volumn 63, Issue 49, 2007, Pages 12160-12165

  Ohta, Kiminori ^a   Yamazaki, Hiroto ^a   Pichierri, Fabio ^b   Kawahata, Masatoshi ^c   Yamaguchi, Kentaro ^c   Endo, Yasuyuki ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

1H NMR study; C H O interaction; DFT calculations; Hydrogen bond; o Carborane; Supramolecular array

Indexed keywords

1 (2 METHOXY 5 AMINOPHENYL) 1,2 DICARBA CLOSO DODECARBORANE; 1 (2 METHOXY 5 NITROPHENYL) 1,2 DICARBA CLOSO DODECARBORANE; 1 (2 METHOXYPHENYL) 1,2 DICARBA CLOSO DODECARBORANE; CARBORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; HYDROPHOBICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 35348936152     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.063     Document Type: Article

References (44)

1. Grimes R.N. Angew. Chem., Int. Ed. Engl. 32 (1993) 1289
2. Hawthorne M.F., and Zheng Z. Acc. Chem. Res. 30 (1997) 267
3. Songkram C., Yamasaki R., Tanatani A., Takaishi K., Yamaguchi K., Kagechika H., and Endo Y. Tetrahedron Lett. 42 (2001) 5913
4. Harada A., and Takahashi S. J. Chem. Soc., Chem. Commun. (1988) 1352
5. Kusukawa T., and Fujita M. Angew. Chem., Int. Ed. 37 (1998) 3142
6. Hardie M.J., and Raston C.L. Chem. Commun. (1999) 1153
7. Frixa C., Scobie M., Black S.J., Thompson A.S., and Threadgill M.D. Chem. Commun. (2002) 2876
8. Kruglyak L.I., Kalinin V.N., Rys E.G., Zakharkin L.I., and Shatenstein A.I. Zh. Obshch. Khim. 42 (1972) 2670
9. Leites L.A. Chem. Rev. 92 (1992) 279
10. Lee H., Knobler C.B., and Hawthorne M.F. Chem. Commun. (2000) 2485
11. Barbera G., Vinas C., Teixidor F., Rosair G.M., and Welch A.J. J. Chem. Soc., Dalton Trans. (2002) 3647
12. Blanch R.J., Williams M., Fallon G.D., Gardiner M.G., Kaddour R., and Raston C.L. Angew. Chem., Int. Ed. 36 (1997) 504
13. Hardie M.J., and Raston C.L. Eur. J. Inorg. Chem. (1999) 195
14. Hardie M.J., Godfrey P.D., and Raston C.L. Chem.-Eur. J. 5 (1999) 1828
15. Ramachandran B.M., Knobler C.B., and Hawthorne M.F. J. Mol. Struct. 785 (2006) 167
16. Davidson M.G., Hibbert T.G., Howard J.A.K., Mackinnon A., and Wade K. Chem. Commun. (1996) 2285
17. Godfrey P.D., Grigsby W.J., Nichols P.J., and Raston C.L. J. Am. Chem. Soc. 119 (1997) 9283
18. Harakas G., Vu T., Knobler C.B., and Hawthorne M.F. J. Am. Chem. Soc. 120 (1998) 6405
19. Macias R., Rath N.P., and Barton L. J. Organomet. Chem. 581 (1999) 39
20. Fox M.A., and Hughes A.K. Coord. Chem. Rev. 248 (2004) 457
21. Alekseyeva E.S., Batsanov A.S., Boyd L.A., Fox M.A., Hibbert T.G., Howard J.A.K., MacBride J.A.H., Mackinnon A., and Wade K. J. Chem. Soc., Dalton Trans. (2003) 475
22. Cappelli A., Giorgi G., Anzini M., Vomero S., Ristori S., Rossi C., and Donati A. Chem.-Eur. J. 10 (2004) 3177
23. Ohta K., Yamazaki H., and Endo Y. Tetrahedron Lett. 47 (2006) 1937
24. Heying L.T., Ager Jr. J.W., Clark S.L., Mangold D.J., Goldstein H.L., Hillman M., Polak R.J., and Szymanski J.W. Inorg. Chem. 2 (1963) 1089
25. Paxson E.T., Callahan P.K., and Hawthorne M.F. Inorg. Chem. 12 (1973) 708
26. In: Silverstein R.M., Bassler G.C., and Morrill T.C. (Eds). Spectrometric Identification of Organic Compounds. 4th ed. (1981), John Wiley, New York, NY 181
27. Endo Y., Songkram C., Ohta K., Kaszynski P., and Yamaguchi K. Tetrahedron Lett. 46 (2005) 699
28. Endo Y., Songkram C., Ohta K., and Yamaguchi K. J. Organomet. Chem. 690 (2005) 2750
29. Bondi A. J. Phys. Chem. 68 (1964) 441
30. Brain P.T., Cowie J., Donohoe D.J., Hnyk D., Rankin D.W.H., Reed D., Reid B.D., Robertson H.E., Welch A.J., Hofmann M., and Schleyer P.v.R. Inorg. Chem. 35 (1996) 1701
31. Thomas R.L., Rosair G.M., and Welch A.J. Acta Crystallogr. C 52 (1996) 1024
32. Sinnokrot M.O., Valeev E.F., and Sherrill C.D. J. Am. Chem. Soc. 124 (2002) 10887
33. Shetty A.S., Zhang J., and Moore J.S. J. Am. Chem. Soc. 118 (1996) 1019
34. Pichierri F. Chem. Phys. Lett. 376 (2003) 781
35. Hawthorne M.F., Berry T.E., and Wegner P.A. J. Am. Chem. Soc. 87 (1965) 4746
36. Iijima T., Endo Y., Tsuji M., Kawachi E., Kagechika H., and Shudo K. Chem. Pharm. Bull. 47 (1999) 398
37. Sheldrick G.M. SHELXS97: Program for the Solution of Crystal Structures (1997), University of Göttingen, Germany
38. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., 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 J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
39. Perdew J.P., Burke K., and Ernzerhof M. Phys. Rev. Lett. 77 (1996) 3865
40. Godbout N., Salahub D.R., Andzelm J., and Wimmer E. Can. J. Chem. 70 (1992) 560
41. Sosa C., Andzelm J., Elkin B.C., Wimmer E., Dobbs K.D., and Dixon D.A. J. Phys. Chem. 96 (1992) 6630
42. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (1988) 899
43. GaussView 3.0; Gaussian: Wallingford, CT, 2004.
44. Schaftenaar G., and Noordik J.H. J. Comput.-Aided Mol. Des. 14 (2000) 123