메뉴 건너뛰기




Volumn 72, Issue 16, 2007, Pages 6162-6170

Synthesis and self-association properties of flexible guanidiniocarbonylpyrrole-carboxylate zwitterions in DMSO: Intra- versus intermolecular ion pairing

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; GUANIDINIOCARBONYLPYRROLE-CARBOXYLATE ZWITTERIONS; ION PAIRING;

EID: 34547625790     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070641d     Document Type: Article
Times cited : (29)

References (60)
  • 2
    • 0034860743 scopus 로고    scopus 로고
    • Bowden, N. B.; Weck, M.; M.; Choi, I. S.; Whitesides, G. M. Acc. Chem. Res. 2001, 34, 231-238;
    • (b) Bowden, N. B.; Weck, M.; M.; Choi, I. S.; Whitesides, G. M. Acc. Chem. Res. 2001, 34, 231-238;
  • 12
    • 0032956037 scopus 로고    scopus 로고
    • Jr
    • (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286;
    • (1999) Acc. Chem. Res , vol.32 , pp. 278-286
    • Rebek, J.1
  • 14
    • 34250899195 scopus 로고    scopus 로고
    • Two recent reviews on the challenge of bringing supramolecular chemistry into water can be found in (a) Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366-2393;
    • Two recent reviews on the challenge of bringing supramolecular chemistry into water can be found in (a) Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366-2393;
  • 16
    • 0043032874 scopus 로고    scopus 로고
    • For a recent review on metallo-supramolecular polymers, see
    • For a recent review on metallo-supramolecular polymers, see Gohy, J.-F.; Lohmeijer, B. G. G.; Schubert, U. S. Chem. Eur. J. 2003, 9, 3472-3479.
    • (2003) Chem. Eur. J , vol.9 , pp. 3472-3479
    • Gohy, J.-F.1    Lohmeijer, B.G.G.2    Schubert, U.S.3
  • 17
    • 0037438509 scopus 로고    scopus 로고
    • For previous work from our group on rigid as well as bis-zwitterions, see a
    • For previous work from our group on rigid as well as bis-zwitterions, see (a) Schmuck, C.; Wienand, W. J. Am. Chem. Soc. 2003, 125, 452-459;
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 452-459
    • Schmuck, C.1    Wienand, W.2
  • 18
  • 21
    • 22744458335 scopus 로고    scopus 로고
    • In principle, ion-pair reinforced hydrogen bonds (ionic or charged H-bonds) are significantly stronger than neutral H-bonds: (a) M. Nautner
    • In principle, ion-pair reinforced hydrogen bonds (ionic or charged H-bonds) are significantly stronger than neutral H-bonds: (a) M. Nautner Chem. Rev. 2005, 105, 213-284;
    • (2005) Chem. Rev , vol.105 , pp. 213-284
  • 26
    • 13344250452 scopus 로고    scopus 로고
    • For reviews on anion recognition including guanidinium cations, see a
    • For reviews on anion recognition including guanidinium cations, see (a) Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105, 67-113;
    • (2005) Chem. Rev , vol.105 , pp. 67-113
    • Schug, K.A.1    Lindner, W.2
  • 32
    • 33750489401 scopus 로고    scopus 로고
    • For some specific examples how folding of flexible molecules affects their properties see: a
    • For some specific examples how folding of flexible molecules affects their properties see: a) Rotger, C.; Neues Pina, M.; Vega, M.; Ballester, P.; Deyà, P. M.; Costa, A. Angew. Chem., Int. Ed. 2006, 45, 6844;
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 6844
    • Rotger, C.1    Neues Pina, M.2    Vega, M.3    Ballester, P.4    Deyà, P.M.5    Costa, A.6
  • 46
  • 48
    • 2542583207 scopus 로고    scopus 로고
    • For a thorough theoretical treatment of ring-chain equlibria in self-assembly and related phenomena, see (a) Chen, C.-C, Dormidontova, E. E. Macromolecules 2004, 37, 3905-3917;
    • For a thorough theoretical treatment of ring-chain equlibria in self-assembly and related phenomena, see (a) Chen, C.-C.; Dormidontova, E. E. Macromolecules 2004, 37, 3905-3917;
  • 58
    • 4544299868 scopus 로고    scopus 로고
    • In the absence of solvent molecules or metal ions, which can stabilize charges, amino acids are neutral in the gas phase for a recent experimental work, see Blanco, S, Lesarri, A, Lopez, J. C, Alonso, J. L. J. Am. Chem. Soc. 2004, 126, 11675-11683
    • In the absence of solvent molecules or metal ions, which can stabilize charges, amino acids are neutral in the gas phase (for a recent experimental work, see Blanco, S.; Lesarri, A.; Lopez, J. C.; Alonso, J. L. J. Am. Chem. Soc. 2004, 126, 11675-11683).
  • 59
    • 85177637941 scopus 로고    scopus 로고
    • Only for arginine does the zwitterionic form come energetically close that of the neutral form because of an internal ion pairing, but it is still less stable (ΔE about +5 kJ/mol, see e.g, a) Julian, R. R, Hodyss, R, Beauchamp, J. L. J. Am. Chem. Soc. 2001, 123, 3577-3583;
    • Only for arginine does the zwitterionic form come energetically close that of the neutral form because of an internal ion pairing, but it is still less stable (ΔE about +5 kJ/mol): see e.g. (a) Julian, R. R.; Hodyss, R.; Beauchamp, J. L. J. Am. Chem. Soc. 2001, 123, 3577-3583;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.