Thermodynamic aspects of the host-guest chemistry of pyrogallol[4]arenes and peralkylated ammonium cations

Tetrahedron

Volumn 65, Issue 13, 2009, Pages 2711-2715

  Schnatwinkel, Bjoern ^a   Rekharsky, Mikhail V ^b   Brodbeck, Ralf ^a   Borovkov, Victor V ^b   Inoue, Yoshihisa ^b   Mattay, Jochen ^a  

^a BIELEFELD UNIVERSITY   (Germany)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; CATION; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYROGALLOL; RESORCINOL;

ALKYLATION; ARTICLE; COMPLEX FORMATION; ENTHALPY; ENTROPY; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR INTERACTION; PRIORITY JOURNAL;

EID: 60649113443     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.066     Document Type: Article

References (77)

1. Böhmer V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713-745
2. Högberg A.G.S. J. Org. Chem. 45 (1980) 4498-4500
3. Beer P.D., Smythe A.C., Tite E.L., and Ibbotson A. J. Organomet. Chem. 376 (1989) C11-C14
4. Cometti G., Dalcanale E., DuVosel A., and Levelut A.M. Chem. Commun. (1990) 163-165
5. Bonsignore S., Dalcanale E., Cometti G., and DuVosel A. Liq. Cryst. 8 (1990) 639-649
6. Abis L., Arrighi V., Cometti G., Dalcanale E., and DuVosel A. Liq. Cryst. 9 (1991) 277-284
7. Dalcanale E., DuVosel A., Levelut A.M., and Malthete. Liq. Cryst. 10 (1991) 185-198
8. Bonsignore S., DuVosel A., Guglielmetti G., Dalcanale E., and Ugozzoli F. Liq. Cryst. 13 (1993) 471-482
9. Ricco M., and Dalcanale E. J. Phys. Chem. 98 (1994) 9002-9008
10. Lippmann T., Dalcanale E., and Mann G. Gazz. Chim. Ital. 125 (1995) 595-599
11. Cram D.J., Jaeger R., and Deshayes K. J. Am. Chem. Soc. 115 (1993) 10111-10116
12. Robbins T.A., Knobler C.B., Bellew D.R., and Cram D.J. J. Am. Chem. Soc. 116 (1994) 111-120
13. Yoon J., Sheu C., Houk K.N., Knobler C.B., and Cram D.J. J. Org. Chem. 61 (1996) 9323-9339
14. Helgeson R.C., Paek K., Knobler C.B., Maverick E.F., and Cram D.J. J. Am. Chem. Soc. 118 (1996) 5590-5604
15. Helgeson R.C., Knobler C.B., and Cram D.J. J. Am. Chem. Soc. 119 (1997) 3229-3244
16. Yoon J., and Cram D.J. Chem. Commun. (1997) 497-498
17. Timmerman P., Verboom W., van Veggel F.C.J.M., van Duynhoven J.P., and Reinhoudt D.N. Angew. Chem., Int. Ed. Engl. 33 (1994) 1292-1295
18. Timmerman P., van Veggel F.C.J.M., van Duynhoven J.P., and Reinhoudt D.N. Angew. Chem., Int. Ed. Engl. 33 (1994) 2345-2348
19. Timmerman P., Nierop K.G.A., Brinks E.A., Verboom W., van Veggel F.C.J.M., van Hoorn W.P., and Reinhoudt D.N. Chem.-Eur. J. 1 (1995) 132-143
20. van Wageningen A.M.A., Timmerman P., van Duynhoven J.P., Verboom W., van Veggel F.C.J.M., and Reinhoudt D.N. Chem.-Eur. J. 3 (1997) 639-654
21. Higler I., Verboom W., van Veggel F.C.J.M., De Jong F., and Reinhoudt D.N. Liebigs Ann. Recl. (1997) 1577-1586
22. Chapman R.G., and Sherman J.C. J. Am. Chem. Soc. 117 (1995) 9081-9082
23. Nakamura K., Sheu C., Keating A.E., Houk K.N., and Sherman J.C. J. Am. Chem. Soc. 119 (1997) 4321-4322
24. Chapman R.G., and Sherman J.C. J. Am. Chem. Soc. 120 (1998) 9818-9826
25. Huisman B., Rudkevich D.M., van Veggel F.C.J.M., and Reinhoudt D.N. J. Am. Chem. Soc. 118 (1996) 3523-3524
26. Huisman B., van Veggel F.C.J.M., and Reinhoudt D.N. Pure Appl. Chem. 70 (1998) 1985-1992
27. Higler I., Timmerman P., Verboom W., and Reinhoudt D.N. J. Org. Chem. 61 (1996) 5920-5931
28. Friggeri A., van Veggel F.C.J.M., Reinhoudt D.N., and Kooyman R.P.H. Langmuir 14 (1998) 5457-5463
29. Boerrigter H., Lugtenberg R.J.W., Egberink R.J.M., Verboom W., Reinhoudt D.N., and Spek A.L. Gazz. Chim. Ital. 127 (1998) 709-716
30. Boerrigter H., Tomasberger T., Verboom W., and Reinhoudt D.N. Eur. J. Org. Chem. (1999) 665-674
31. Huisman B., Rudkevich D.M., Farran A., Verboom W., van Veggel F.C.J.M., and Reinhoudt D.N. Eur. J. Org. Chem. (2000) 269-274
32. Luetzen A., Renslo A.R., Schalley C.A., O'Leary B.M., and Rebek Jr. J. J. Am. Chem. Soc. 121 (1999) 7455-7456
33. Chapman R.G., and Sherman J.C. J. Org. Chem. 65 (2000) 513-516
34. Friggeri A., van Veggel F.C.J.M., and Reinhoudt D.N. Chem.-Eur. J. 5 (1999) 3595-3602
35. Chitry F., Pellet-Rostaing S., Nicod L., Gass J., Foos J., Guy A., and Lemaire M. J. Phys. Chem. A 104 (2000) 4121-4128
36. Piatnitski E.L., Flowers R.A., and Deshayes K. Chem.-Eur. J. 6 (2000) 999-1006
37. Letzel M.C., Agena C., and Mattay J. J. Mass Spectrom. 37 (2002) 63-68
38. Beyeh N.K., Kogej M., Ahman A., Rissanen K., and Schalley C.A. Angew. Chem., Int. Ed. 45 (2006) 5214-5218
39. Gerkensmeier T., Iwanek W., Agena C., Fröhlich R., Kotila S., Näther C., and Mattay J. Eur. J. Org. Chem. (1999) 2257-2262
40. Atwood J.L., Barbour J.L., and Jerga A. Chem. Commun. (2001) 2376-2377
41. Shivanyuk A., and Rebek Jr. J. Chem. Commun. (2001) 2374-2375
42. Avram L., and Cohen Y. Org. Lett. 5 (2003) 3329-3332
43. McKinlay R.M., Thallapally P.K., and Atwood J.L. Chem. Commun. (2006) 2956-2958
44. Heaven M.W., Cave G.W.V., McKinlay R.M., Antesberger J., Dalgarno S.J., Thallapally P.K., and Atwood J.L. Angew. Chem., Int. Ed. 45 (2006) 6221-6224
45. Dalgarno S.J., Bassil D.B., Tucker S.A., and Atwood J.L. Angew. Chem., Int. Ed. 45 (2006) 7019-7022
46. Power N.P., Dalgarno S.J., and Atwood J.L. New J. Chem. 31 (2007) 17-20
47. Dalgarno S.J., Power N.P., and Atwood J.L. Chem. Commun. (2007) 3447-3449
48. Dalgarno S.J., Antesberger J., McKinlay R.M., and Atwood J.L. Chem.-Eur. J. 13 (2007) 8248-8255
49. Power N.P., Dalgarno S.J., and Atwood J.L. Angew. Chem., Int. Ed. 46 (2007) 8601-8604
50. Dalgarno S.J., Power N.P., Warren J.E., and Atwood J.L. Chem. Commun. (2008) 1539-1541
51. Ahman A., Nissinen M., and Rissanen K. Supramol. Chem. 16 (2004) 505-512
52. Ahman A., Luostarinen M., Schalley C.A., Nissinen M., and Rissanen K. Eur. J. Org. Chem. (2005) 2793-2801
53. Mansikkamäki H., Nissinen M., and Rissanen K. Cryst. Eng. Commun. 7 (2005) 519-526
54. Mansikkamäki H., Schalley C.A., Nissinen M., and Rissanen K. New J. Chem. 29 (2005) 116-127
55. Ahman A., Luostarinen M., Rissanen K., and Nissinen M. New J. Chem. 31 (2007) 169-177
56. For a review, see:. Ma J.C., and Dougherty D.A. Chem. Rev. 97 (1997) 1303-1324
57. Casnati A., Sciotto D., and Arena G. In: Asfari Z., Böhmer V., Harrowfield V., and Vicens J. (Eds). Calixarenes (2001), Kluwer Academic, Dordrecht, Netherland Chapter 24, and references therein
58. Schneider H.-J., Gattes D., and Schneider U. J. Am. Chem. Soc. 110 (1988) 6449-6454
59. For a review, see:. Ludwig R. Microchim. Acta 152 (2005) 1-19
60. Danil de Namor A.F., Cleverley R.M., and Zapata-Ormachchea M.L. Chem. Rev. 98 (1998) 2495-2525
61. Saha A., Nayak S.K., Chattopadhyay S., and Mukherjee A.K. J. Phys. Chem. A 108 (2004) 8223-8228
62. Sarmentero M.A., and Ballester P. Org. Biomol. Chem. 5 (2007) 3046-3054
63. Ballester P., Shivanyuk A., Far A.F., and Rebek Jr. J. J. Am. Chem. Soc. 124 (2002) 14014-14016
64. Higler I., Grave L., Breuning E., Verboom W., de Jong F., Fyles T.M., and Reinhoudt D.N. Eur. J. Org. Chem. (2000) 1727-1734
65. Eckel R., Ros R., Decker B., Mattay J., and Anselmetti D. Angew. Chem., Int. Ed. 44 (2005) 484-488
66. Tafi A., Botta B., Delle Monache G., Fillipi A., and Speranza M. Chem.-Eur. J. 10 (2004) 4126-4135
67. Schnatwinkel B., Stoll I., Mix A., Rekharsky M.V., Borovkov V.V., Inoue Y., and Mattay J. Chem. Commun. (2008) 3873-3875
68. Rekharsky M.V., and Inoue Y. J. Am. Chem. Soc. 122 (2000) 4418-4435
69. 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., 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. Gaussian03, Revision C.02 (2004), Gaussian, Wallingford, CT
70. Becke A.D. Phys. Rev. A: Gen. Phys. 38 (1988) 3098-3100
71. Vosko S.H., Wilk L., and Nusair N. Can. J. Phys. 58 (1980) 1200-1211
72. Perdew J.P. Phys. Rev. B: Condens. Matter 33 (1986) 8822-8824
73. Schäfer A., Huber C., and Ahlrichs R. J. Chem. Phys. 100 (1994) 5829-5835
74. Dunlap B.I. J. Chem. Phys. 78 (1983) 3140-3142
75. Dunlap B.I. J. Mol. Struct. (THEOCHEM) 529 (2000) 37-40
76. van Duijneveldt F.B., van Duijneveldt-van de Rijdt J.G.C.M., Nielsen I.M.B., and van Lenthe J.H. Chem. Rev. 94 (1994) 1873-1885
77. Boys S.F., and Bernardi F. Mol. Phys. 19 (1970) 553-566