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Volumn 132, Issue 16, 2010, Pages 5869-5879

Synthesis, structural investigations, hydrogen-deuterium exchange studies, and molecular modeling of conformationally stablilized aromatic oligoamides

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO; AMIDE HYDROGENS; AROMATIC OLIGOAMIDES; COMPUTATIONAL STUDIES; CONFORMATIONAL PREFERENCES; HELICAL CONFORMATION; HEXAMERS; HYDROGEN-BONDING STRENGTH; HYDROGEN-DEUTERIUM EXCHANGE; INTRAMOLECULAR HYDROGEN BOND; ION-CONDUCTING; OLIGOAMIDES; ONE-DIMENSIONAL STRUCTURE; PENTAMERS; QUANTUM-MECHANICAL CALCULATION; SOLID-STATE STRUCTURES; STRUCTURAL INVESTIGATION; TETRAMERS; WEAK POINTS;

EID: 77952564580     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100579z     Document Type: Article
Times cited : (76)

References (158)
  • 31
    • 33748216403 scopus 로고
    • For some selected folding helices supported by solid-state structures, see
    • For some selected folding helices supported by solid-state structures, see: Hamuro, Y., Geib, S. J., and Hamilton, A. D. Angew. Chem., Int. Ed. 1994, 33, 446
    • (1994) Angew. Chem., Int. Ed. , vol.33 , pp. 446
    • Hamuro, Y.1    Geib, S.J.2    Hamilton, A.D.3
  • 46
    • 0034598516 scopus 로고    scopus 로고
    • For some selected folding helices with solid-state structures remaining unknown, see
    • For some selected folding helices with solid-state structures remaining unknown, see: Cuccia, L. A., Lehn, J.-M., Homo, J.-C., and Schmutz, M. Angew. Chem., Int. Ed. 2000, 39, 233
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 233
    • Cuccia, L.A.1    Lehn, J.-M.2    Homo, J.-C.3    Schmutz, M.4
  • 157
    • 77952566325 scopus 로고    scopus 로고
    • For ortho-substituted isomers rigidified by only one H-bond (two such isomers can be generated for an oligomer as simple as 2a by flipping one benzene ring to disrupt one H-bond while keeping the other intact), the distance between amide proton and protons of methoxy group whose oxygen atom is not involved in H-bond would be close to or larger than 5 Å. For methoxy group involved, one of its protons will be less than 3 Å away from the amide proton. This suggests that probably only one NOE can be detected for every amide proton for these two alternative isomers containing only one H-bond. Or conservatively, one strong and one very weak NOE should be seen. This differs from the isomers containing two H-bonds (i.e., three-center H-bonding system in 2a or a continuous H-bonding network in oligomers 3 - 6) where two NOEs with comparable intensities should be seen between every amide proton and its two neighboring methoxy methyl groups
    • For ortho-substituted isomers rigidified by only one H-bond (two such isomers can be generated for an oligomer as simple as 2a by flipping one benzene ring to disrupt one H-bond while keeping the other intact), the distance between amide proton and protons of methoxy group whose oxygen atom is not involved in H-bond would be close to or larger than 5 Å. For methoxy group involved, one of its protons will be less than 3 Å away from the amide proton. This suggests that probably only one NOE can be detected for every amide proton for these two alternative isomers containing only one H-bond. Or conservatively, one strong and one very weak NOE should be seen. This differs from the isomers containing two H-bonds (i.e., three-center H-bonding system in 2a or a continuous H-bonding network in oligomers 3 - 6) where two NOEs with comparable intensities should be seen between every amide proton and its two neighboring methoxy methyl groups.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.