Directed H-bonding inhibition in molecular recognition: An NMR case study of the H-bonding of a dicarboxylic acid with a new mixed diamide receptor having one adjacent pyridine-N-oxide

Tetrahedron Letters

Volumn 46, Issue 8, 2005, Pages 1315-1318

  Goswami, Shyamaprosad ^a   Dey, Swapan ^a   Maity, Annada C ^a   Jana, Subrata ^a  

^a INDIAN INSTITUTE OF ENGINEERING SCIENCE AND TECHNOLOGY   (India)

Author keywords

Adipic and propionic acids; Inhibition of hydrogen bonding; Molecular recognition; Pyridine N oxides

Indexed keywords

ADIPIC ACID; AMIDE; CARBOXYL GROUP; DIAMIDE; DICARBOXYLIC ACID; PROPIONIC ACID; PYRIDINE; PYRIDINE 1 OXIDE;

ARTICLE; CHEMICAL BINDING; CHEMICAL PROCEDURES; CHEMICAL REACTION; HYDROGEN BOND; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 13244255376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.121     Document Type: Article

References (19)

1. J.M. Lehn Supramolecular Chemistry: Concepts and Perspectives 1995 VCH Weinheim
2. S.P. Goswami, D.V. Engen, and A.D. Hamilton J. Am. Chem. Soc. 111 1989 3425
3. J.C. MacDonald, and G.M. Whitesides Chem. Rev. 94 1994 2383
4. C. Alvarez-Rua, S. García-Granda, S.P. Goswami, R. Mukherjee, S. Dey, R.M. Claramunt, M.D.S. María, I. Rozas, N. Jagerovic, I. Alkorta, and J. Elguero New J. Chem. 28 2004 700
5. R.J. Fitzmaurice, G.M. Kyne, D. Douheret, and J.D. Kilburn J. Chem. Soc., Perkin Trans. 1 7 2002 841
6. S.P. Goswami, K. Ghosh, and S. Dasgupta Tetrahedron 52 1996 12223
7. S.P. Goswami, K. Ghosh, and R. Mukherjee J. Ind. Chem. Soc. 1999 661
8. S.P. Goswami, K. Ghosh, and S. Dasgupta J. Org. Chem. 65 2000 1907
9. S.P. Goswami, K. Ghosh, and M. Halder Tetrahedron Lett. 40 1999 1735
10. F. Garcia-Tellado, S.P. Goswami, S.K. Chang, S.J. Geib, and A.D. Hamilton J. Am. Chem. Soc. 112 1990 7393
11. S. Geib, F. Garcia-Tellado, S.P. Goswami, and A.D. Hamilton J. Am. Chem. Soc. 113 1991 9265
12. 3 was added slowly and carefully to neutralize the mixture at room temperature, which was then extracted with chloroform. The organic layer was washed with water, dried and purified over silica gel by preparative TLC using 5% methanol in chloroform. Compound 1 was isolated as a white solid (140 mg, 38%, mp 205-206°C). Compound 2 was obtained from the more polar spot [130 mg, 34%, mp 250°C(d)]
13. 3, 300 MHz): δ 10.21 (br s, 1H), 8.36 (br s, 1H), 7.20 (br s, 1H), 7.01 (br s, 1H), 2.66 (s, 3H), 2.33 (s, 3H)
14. S.P. Goswami, K. Ghosh, A.K. Mahapatra, G.D. Nigam, K. Chinnakali, and H.K. Fun Acta Crystallogr. C-55 1999 579
15. S.P. Goswami, K. Ghosh, and R. Mukherjee Supramol. Chem. 1999 191
16. By Foster-Fyfe analysis of the titration data at 25°C F. Foster, and C.A. Fyfe Prog. Nucl. Magn. Reson. Spectrosc. 4 1969 1
17. S.P. Goswami, K. Ghosh, and R. Mukherjee Tetrahedron 57 2001 4987
18. S.P. Goswami, and K. Ghosh Tetrahedron Lett. 38 1997 4503
19. pcmodel Serena Software 93