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Volumn 121, Issue 48, 1999, Pages 11156-11163

Transfer of chiral information through molecular assembly

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

EID: 0033537031     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993165k     Document Type: Article
Times cited : (136)

References (67)
  • 7
    • 0038359860 scopus 로고    scopus 로고
    • Reversible Dimerization of Tetraureas Derived from Calix[4]arenes
    • M. Pons, ed.; NATO ASI Series, Ser. C; Kluwer Academic Publishers: Dordrecht, The Netherlands
    • (d). Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASI Series, Ser. C; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; Vol. 526, pp 45-60.
    • (1999) NMR in Supramolecular Chemistry , vol.526 , pp. 45-60
    • Böhmer, V.1    Mogck, O.2    Pons, M.3    Paulus, E.F.4
  • 12
    • 84920344508 scopus 로고    scopus 로고
    • Heterodimerization propensity was found to be solvent-dependent
    • Heterodimerization propensity was found to be solvent-dependent.
  • 13
    • 84920343921 scopus 로고    scopus 로고
    • Statistically, 1:1 combination of homodimers AA and BB gives heterodimers AB and BA, equivalent species, as 50% of the mixture. See ref 2a for details
    • Statistically, 1:1 combination of homodimers AA and BB gives heterodimers AB and BA, equivalent species, as 50% of the mixture. See ref 2a for details.
  • 35
    • 84920361685 scopus 로고    scopus 로고
    • Compounds 3-10 do, however, show at best statistical heterodimerization with the enantiomers of 5 and 6, derived from D-isoleucine and D-valine, respectively
    • Compounds 3-10 do, however, show at best statistical heterodimerization with the enantiomers of 5 and 6, derived from D-isoleucine and D-valine, respectively.
  • 36
    • 84920356004 scopus 로고    scopus 로고
    • CW and CCW refer to the head-to-tail urea directionality when viewed from the narrow rim of the arylurea 1 in the heterodimer. R or S refers to the absolute stereochemistry of the amino acid side chains
    • CW and CCW refer to the head-to-tail urea directionality when viewed from the narrow rim of the arylurea 1 in the heterodimer. R or S refers to the absolute stereochemistry of the amino acid side chains.
  • 37
    • 0033551825 scopus 로고    scopus 로고
    • and references therein
    • Possibly observed here, CH/π interactions can significantly influence molecular conformation: Umezawa, Y.; Tsuboyama, S.; Takahashi, H.; Uzawa, J.; Nishio, M. Tetrahedron 1999, 55, 10047-10056 and references therein.
    • (1999) Tetrahedron , vol.55 , pp. 10047-10056
    • Umezawa, Y.1    Tsuboyama, S.2    Takahashi, H.3    Uzawa, J.4    Nishio, M.5
  • 38
    • 84920351538 scopus 로고    scopus 로고
    • note
    • 6. Upon heating from 295 to 345 K the heterodimer concentration decreases by 20%, and assembly is driven to the homodimeric states, in agreement with entropic arguments, while the selectivity remains essentially unchanged. See the Supporting Information for details.
  • 40
    • 84920352136 scopus 로고    scopus 로고
    • 7 varies from 8.56 ppm for 7 to 8.23 ppm for 10. The distal -NH shifts from 6.90 ppm in 9 to 6.24 ppm in 8
    • 7 varies from 8.56 ppm for 7 to 8.23 ppm for 10. The distal -NH shifts from 6.90 ppm in 9 to 6.24 ppm in 8.
  • 41
    • 0031781176 scopus 로고    scopus 로고
    • Essentially identical results were obtained for assembly 1-6 (Supporting Information). For CD in related molecular recognition studies see: (a) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chein. Soc. 1998, 120, 6185-6186.
    • (1998) J. Am. Chein. Soc. , vol.120 , pp. 6185-6186
    • Huang, X.1    Rickman, B.H.2    Borhan, B.3    Berova, N.4    Nakanishi, K.5
  • 47
    • 84920351580 scopus 로고    scopus 로고
    • The sensitivity of these highly cooperative assemblies to solvents that compete for hydrogen bonds, e.g. methanol, DMSO, and DMF, has been reported. See refs 2 and 4 for details
    • The sensitivity of these highly cooperative assemblies to solvents that compete for hydrogen bonds, e.g. methanol, DMSO, and DMF, has been reported. See refs 2 and 4 for details.
  • 55
    • 84920350191 scopus 로고    scopus 로고
    • Reference 18c
    • (h) Reference 18c.
  • 60
    • 84920347305 scopus 로고    scopus 로고
    • The second, bold-faced R or S represents the stereochemistry of the guest
    • The second, bold-faced R or S represents the stereochemistry of the guest.
  • 61
    • 84920346112 scopus 로고    scopus 로고
    • Similar selectivity is also observed in the binding of β-butyrolactone. This guest is not bound in the 1-2 heterodimer
    • Similar selectivity is also observed in the binding of β-butyrolactone. This guest is not bound in the 1-2 heterodimer.
  • 62
    • 84920354766 scopus 로고    scopus 로고
    • Although encapsulated, 3-methylcyclopentanone is a relatively poor guest for assembly 1-2
    • Although encapsulated, 3-methylcyclopentanone is a relatively poor guest for assembly 1-2.
  • 63
    • 84920359740 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.