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Volumn 74, Issue 1, 2009, Pages 48-57

Isotopic perturbation of the conformational equilibrium in methylene-functionalized calixarenes

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENES; CHEMICAL EQUATIONS; CONFORMATIONAL EQUILIBRIUMS; DEUTERATION; DEUTERIUM ATOMS; EXTERNAL-; FUNCTIONALIZED; HYDROXYL GROUPS; ISOTOPIC ENRICHMENTS; ISOTOPOLOGUES; ISOTOPOMERS; METHOXY GROUPS; NMR SPECTRUMS; OH GROUPS; RESIDUAL WATERS; STATISTICAL DISTRIBUTIONS; X-RAY STRUCTURES;

EID: 58149289856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8020538     Document Type: Article
Times cited : (17)

References (56)
  • 1
    • 0003433022 scopus 로고
    • For reviews on calixarenes, see: a, Vicens, J, Böhmer, V, Eds, Kluwer: Dordrecht
    • For reviews on calixarenes, see: (a) Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991.
    • (1991) Calixarenes, a Versatile Class of Macrocyclic Compounds
  • 5
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    • Royal Society of Chemistry: Cambridge
    • (e) Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
    • (1998) Calixarenes Revisited
    • Gutsche, C.D.1
  • 6
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Vicens, J, Eds, Kluwer: Dordrecht
    • (f) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer: Dordrecht, 2001.
    • (2001) Calixarenes 2001
  • 7
    • 0345736841 scopus 로고    scopus 로고
    • Rappoport, Z, Ed, Wiley: Chichester, Chapter 19
    • (g) Böhmer, V. In The Chemistry of Phenols; Rappoport, Z., Ed.; Wiley: Chichester, 2003; Chapter 19.
    • (2003) The Chemistry of Phenols
    • Böhmer, V.1
  • 19
    • 58149308946 scopus 로고    scopus 로고
    • Four isomers are possible for a calix[4]arene derivative with the four bridges identically substituted see ref 4, These forms are configurational isomers and not conformers since their mutual interconversion requires cleavage of bonds
    • Four isomers are possible for a calix[4]arene derivative with the four bridges identically substituted (see ref 4). These forms are configurational isomers and not conformers since their mutual interconversion requires cleavage of bonds.
  • 20
    • 58149296656 scopus 로고    scopus 로고
    • The conformation of calix[4]arenes is usually discussed in terms of four basic forms (cone, partial cone, 1,3-alternate, and 1,2-alternate, ref 1) arising form the different possible up or down arrangements of the aryl rings. Rotation through the annulus of the rings mutually interconverts these forms.
    • The conformation of calix[4]arenes is usually discussed in terms of four basic forms (cone, partial cone, 1,3-alternate, and 1,2-alternate, ref 1) arising form the different possible "up" or "down" arrangements of the aryl rings. Rotation through the annulus of the rings mutually interconverts these forms.
  • 21
    • 58149288756 scopus 로고    scopus 로고
    • A calix[4]arene of unknown stereochemistry monofunctionalized at four bridges with OH groups was prepared by Görmar and coworkers via LiAlH 4 reduction of a ketocalixarene. See ref 3a
    • 4 reduction of a ketocalixarene. See ref 3a.
  • 24
    • 0001365719 scopus 로고
    • For selected applications of the isotopic perturbation method, see, for example: a
    • For selected applications of the isotopic perturbation method, see, for example: (a) Saunders, M.; Kates, M. R. J. Am. Chem. Soc. 1977, 99, 8071.
    • (1977) J. Am. Chem. Soc , vol.99 , pp. 8071
    • Saunders, M.1    Kates, M.R.2
  • 38
    • 0000794164 scopus 로고    scopus 로고
    • For examples of isotopic multiplets in polyols. see: (a) Reuben, J. J. Am. Chem. Soc. 1983, 105, 3711
    • For examples of isotopic multiplets in polyols. see: (a) Reuben, J. J. Am. Chem. Soc. 1983, 105, 3711.
  • 48
    • 0001070727 scopus 로고    scopus 로고
    • Statistical analysis of the crystal structure data of the methoxyphenyl group in different environments has shown that the perpendicular conformation of the methoxy group is preferred if the two ortho positions are substituted. See: Hummel, W, Huml, K, Bürgi, H.-B. Helv. Chim. Acta 1988, 71, 1291
    • Statistical analysis of the crystal structure data of the methoxyphenyl group in different environments has shown that the perpendicular conformation of the methoxy group is preferred if the two ortho positions are substituted. See: Hummel, W.; Huml, K.; Bürgi, H.-B. Helv. Chim. Acta 1988, 71, 1291.
  • 49
    • 58149314677 scopus 로고    scopus 로고
    • This epimerization process most likely involves cleavage of the C-OH bonds and is probably catalyzed by acidic impurities in the solvent
    • This epimerization process most likely involves cleavage of the C-OH bonds and is probably catalyzed by acidic impurities in the solvent.
  • 50
    • 58149286680 scopus 로고    scopus 로고
    • It has been shown by Reuben for partially deuterated polyols ref 11, that the chemical exchange between proton and deuteron in the hydroxy groups is slow on the NMR timescale
    • It has been shown by Reuben for partially deuterated polyols (ref 11). that the chemical exchange between proton and deuteron in the hydroxy groups is slow on the NMR timescale.
  • 51
    • 58149311594 scopus 로고    scopus 로고
    • Two species are isotopologues if they differ only in the number of isotopic substitutions (i.e., the isotopic composition). Isotopomers refer to isomers differing only in the position of the isotopic substitution in the skeleton. See: Müller. P. Pure Appl. Chem. 1994, 66, 1077.
    • Two species are isotopologues if they differ only in the number of isotopic substitutions (i.e., the isotopic composition). Isotopomers refer to isomers differing only in the position of the isotopic substitution in the skeleton. See: Müller. P. Pure Appl. Chem. 1994, 66, 1077.
  • 52
    • 0347832970 scopus 로고    scopus 로고
    • For a study on hydrogen isotope fractionation factors, see, for example
    • For a study on hydrogen isotope fractionation factors, see, for example: Guo, H. X.; Kresge, A. J. J. Chem. Soc., Perkin. Trans. 2 1997, 295.
    • (1997) J. Chem. Soc., Perkin. Trans. 2 , pp. 295
    • Guo, H.X.1    Kresge, A.J.2
  • 53
    • 58149290345 scopus 로고    scopus 로고
    • The percent of deuteration was determined from the ratio between the integration of the HOD signal and the sum of the total integration of the H 2O and HDO signals
    • 2O and HDO signals.
  • 56
    • 58149288753 scopus 로고    scopus 로고
    • gNMR v4.1.0. Cherwell Scientific Publishing, Oxford, UK.
    • gNMR v4.1.0. Cherwell Scientific Publishing, Oxford, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.