NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

Structural Chemistry

Volumn 21, Issue 5, 2010, Pages 1061-1067

  Ośmiałowski, Borys ^a   Kolehmainen, Erkki ^b   Gawinecki, Ryszard ^a   Kauppinen, Reijo ^b   Koivukorpi, Juha ^b   Valkonen, Arto ^b  

^a UNIVERSITY OF TECHNOLOGY AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Association; DFT calculations; Hydrogen bond; NMR; Selective binding

Indexed keywords

EID: 77956886455     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-010-9646-2     Document Type: Article

References (65)

1. Watson JD, Crick FHC (1953) Nature 171: 737.
2. Jeffrey GA, Saenger W (1994) Hydrogen bonding in biological structures, study edition. Springer, Berlin.
3. Eldrup AB, Christensen C, Haaima G, Nielsen PE (2002) J Am Chem Soc 124: 3254.
4. Prins LJ, Reinhoudt DN, Timmerman P (2001) Angew Chem Int Ed 40: 2382.
5. Lehn J-M (2000) In: Ciferri A (ed) Supramolecular polymer chemistry-scope and perspectives. Marcel Dekker, New York.
6. Brunsveld L, Folmer BJB, Meijer EW, Sijbesma RP (2001) Chem Rev 101: 4071.
7. De Greef TFA, Smulders MMJ, Wolffs M, Schenning APHJ, Sijbesma RP, Meijer EW (2009) Chem Rev 109: 5687.
8. Alvares-Rua C, Garcia-Granda S, Goswami S, Mukherjee R, Dey S, Claramunt RM, Santa Maria MD, Rozas I, Jagerovic N, Alkorta I, Elguero J (2004) New J Chem 28: 700.
9. Newman SG, Taylor A, Boyd RJ (2008) Chem Phys Lett 450: 210.
10. Pranata J, Wierschke SG, Jorgensen WL (1991) J Am Chem Soc 113: 2810.
11. Jorgensen WL, Pranata J (1990) J Am Chem Soc 112: 2008.
12. Taubitz J, Lüning U (2009) Aust J Chem 62: 1550.
13. Sijbesma RP and Meijer EW (2003) Chem. Commun. 5.
14. Blight BA, Camara-Campos A, Djurdjevic S, Kaller M, Leigh DA, McMillan FM, McNab H, Slawin AMZ (2009) J Am Chem Soc 131: 14116.
15. Murray TJ, Zimmerman SC, Kolotuchin SV (1995) Tetrahedron 51: 635.
16. Bell DA, Anslyn EV (1995) Tetrahedron 51: 7161.
17. Djurdjevic S, Leigh DA, McNab H, Parsons S, Teobaldi G, Zerbetto F (2007) J Am Chem Soc 129: 476.
18. Hisamatsu Y, Fukumi Y, Shirai N, Ikeda S-i, Odashima K (2008) Tetrahedron Lett 49: 2005.
19. McGhee AM, Kilner C, Wilson AJ (2008) Chem Commun 344.
20. Xu W, Li X-C, Tan H, Chen G-J (2006) Phys Chem Chem Phys 8: 4427.
21. Park TK, Schroeder J, Rebek J (1991) J Am Chem Soc 113: 5125.
22. Gooch A, McGhee AM, Renton LC, Plante JP, Lindsay CI, Wilson AJ (2009) Supramol Chem 21: 12.
23. Sontjens SHM, Sijbesma RP, van Genderen MHP, Meijer EW (2000) J Am Chem Soc 122: 7487.
24. Schneider H-J (2009) Angew Chem Int Ed 48: 3924.
25. Scherman OA, Ligthart GBWL, Sijbesma RP, Meijer EW (2006) Angew Chem Int Ed 45: 2072.
26. Brammer S, Lüning U, Kühl C (2002) Eur J Org Chem 2002: 4054.
27. Manesiotis P, Hall AJ, Sellergren B (2005) J Org Chem 70: 2729.
28. Brown HC (1945) J Am Chem Soc 67: 378.
29. Brown HC (1945) J Am Chem Soc 67: 1452.
30. Lüning U, Kühl C (1998) Tetrahedron Lett 39: 5735.
31. Luening U, Kuhl C, Uphoff A (2002) Eur J Org Chem 2002: 4063.
32. Benoit RL, Fréchette M, Lefebvre D (1988) Can J Chem 66: 1159.
33. Beijer FH, Sijbesma RP, Vekemans JAJM, Meijer EW, Kooijman H, Spek AL (1996) J Org Chem 61: 6371.
34. Llanes-Pallas A, Matena M, Jung T, Prato M, Stohr M, Bonifazi D (2008) Angew Chem Int Ed 47: 7726.
35. Li Z, Ding J, Robertson G, Day M, Tao Y (2005) Tetrahedron Lett 46: 6499.
36. Katsuhiro I (2010) Chem Commun 2947.
37. Ikeda C, Nagahara N, Motegi E, Yoshioka N, Inoue H (1999) Chem Commun 1759.
38. Liu Y, Li Y, Jiang L, Gan H, Liu H, Li Y, Zhuang J, Lu F, Zhu D (2004) J Org Chem 69: 9049.
39. Liu Y, Zhuang J, Liu H, Li Y, Lu F, Gan H, Jiu T, Wang N, He X, Zhu D (2004) Chem Phys Chem 5: 1210.
40. Schmidt J, Schmidt R, Wurthner F (2008) J Org Chem 73: 6355.
41. Kang SO, Day VW, Bowman-James K (2009) J Org Chem 75: 277.
42. Lo PK, Sleiman HF (2008) Macromolecules 41: 5590.
43. Xu Z, Daka P, Wang H (2009) Chem Commun 6825.
44. Chattopadhyay P, Pandey PS (2007) Bioorg Med Chem Lett 17: 1553.
45. Bolz I, Moon C, Enkelmann V, Brunklaus G, Spange S (2008) J Org Chem 73: 4783.
46. Forbes CC, Beatty AM, Smith BD (2001) Org Lett 3: 3595.
47. Feibush B, Figueroa A, Charles R, Onan KD, Feibush P, Karger BL (1986) J Am Chem Soc 108: 3310.
48. Breinlinger E, Niemz A, Rotello VM (1995) J Am Chem Soc 117: 5379.
49. Bolz I, Spange S (2008) Chem Eur J 14: 9338.
50. Chattopadhyay P, Pandey PS (2006) Tetrahedron 62: 8620.
51. Murray TJ, Zimmerman SC (1992) J Am Chem Soc 114: 4010.
52. Fenlon EE, Murray TJ, Baloga MH, Zimmerman SC (1993) J Org Chem 58: 6625.
53. Leung M-K, Mandal AB, Wang C-C, Lee G-H, Peng S-M, Cheng H-L, Her G-R, Chao I, Lu H-F, Sun Y-C, Shiao M-Y, Chou P-T (2002) J Am Chem Soc 124: 4287.
54. Farrugia LJ (1997) J Appl Crystallogr 30: 565.
55. Osmialowski B (2009) J Mol Struct THEOCHEM 908: 92.
56. Bernstein J, Stearns B, Shaw E, Lott WA (1947) J Am Chem Soc 69: 1151.
57. Kurita K, Williams RL (1975) J Heterocycl Chem 12: 789.
58. Kolehmainen E, Ośmiałowski B, Krygowski TM, Kauppinen R, Nissinen M, Gawinecki R (2000) J Chem Soc Perkin Trans 2: 1259.
59. Benesi H, Hildebrand J (1949) J Am Chem Soc 71: 2703.
60. Otwinowski Z, Minor W (1997) Methods in enzymology. In: Carter CW, Sweet RM (eds) Macromolecular crystallography, vol 276. Academic Press, New York.
61. Burla MC, Camalli M, Carrozzini B, Cascarano GL, Giacovazzo C, Polidori G, Spagna R (2005) J Appl Crystallogr 38: 381.
62. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, Pidcock E, McCabe P, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) J Appl Crystallogr 41: 466.
63. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery J, J. A., 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 (2004) Gaussian 03, Revision E. 01. Gaussian Inc., Pittsburgh.
64. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA (1993) J Comput Chem 14: 1347.
65. Baldridge KK, Greenberg JP (1995) J Mol Graph 13: 63.