Intramolecular hydrogen bonding studies for a series of dipurinyl-2,6-pyridinedicarboxamides

被引:17
作者
Crisp, GT [1 ]
Jiang, YL [1 ]
机构
[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia
基金
澳大利亚研究理事会;
关键词
D O I
10.1016/S0040-4020(98)01053-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of potential receptor molecules based on the dipurinyl-2,6-pyridinedicarboxamide motif has been prepared and the intramolecular hydrogen bonding characterised by H-1 NMR and FT-IR spectroscopies. The hydrogen bonding gives rise to a preferential planar, cis conformation for the molecules. The planar nature of the unit also gives rise to pi-pi: stacking as shown by H-1 NMR dilution experiments. (C) 1998 Elsevier Science Ltd. AII rights reserved.
引用
收藏
页码:549 / 560
页数:12
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共 26 条
  • [1] Effect of the 1-(2'-deoxy-beta-D-ribofuranosyl)-3-nitropyrrole residue on the stability of DNA duplexes and triplexes
    Amosova, O
    George, J
    Fresco, JR
    [J]. NUCLEIC ACIDS RESEARCH, 1997, 25 (10) : 1930 - 1934
  • [2] DIRECTED MACROCYCLIZATION REACTIONS
    CARVER, FJ
    HUNTER, CA
    SHANNON, RJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (10) : 1277 - 1280
  • [3] H-1 AND C-13 NUCLEAR MAGNETIC-RESONANCE STUDIES ON PURINE
    CHENG, DM
    KAN, LS
    TSO, POP
    GIESSNERPRETTRE, C
    PULLMAN, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) : 525 - 534
  • [4] Self-assembly of macrocyclic porphyrin oligomers
    Chi, XL
    Guerin, AJ
    Haycock, RA
    Hunter, CA
    Sarson, LD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) : 2567 - 2569
  • [5] DOMINANCE OF POLAR/PI OVER CHARGE-TRANSFER EFFECTS IN STACKED PHENYL INTERACTIONS
    COZZI, F
    CINQUINI, M
    ANNUZIATA, R
    SIEGEL, JS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5330 - 5331
  • [6] Elaboration of the side-chain of amino acid derivatives by palladium catalysed couplings
    Crisp, GT
    Jiang, YL
    Pullman, PJ
    DeSavi, C
    [J]. TETRAHEDRON, 1997, 53 (51) : 17489 - 17500
  • [7] N-alpha-benzoyl-cis-4-amino-L-proline: A gamma-turn mimetic
    Curran, TP
    Chandler, NM
    Kennedy, RJ
    Keaney, MT
    [J]. TETRAHEDRON LETTERS, 1996, 37 (12) : 1933 - 1936
  • [8] A novel 2'-deoxynucleoside designed for enhanced recognition of A.T. base-pairs.
    Czernecki, S
    Hoang, A
    Valery, JM
    [J]. TETRAHEDRON LETTERS, 1996, 37 (49) : 8857 - 8860
  • [9] STRUCTURAL AND THERMODYNAMIC CHARACTERIZATION OF TEMPERATURE-DEPENDENT CHANGES IN THE FOLDING PATTERN OF A SYNTHETIC TRIAMIDE
    DADO, GP
    GELLMAN, SH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4228 - 4245
  • [10] Conformational restriction by intramolecular hydrogen bonding. Carbohydrate-carbohydrate self-assembly.
    delaPaz, ML
    Ellis, G
    Penades, S
    Vicent, C
    [J]. TETRAHEDRON LETTERS, 1997, 38 (09) : 1659 - 1662