메뉴 건너뛰기




Volumn 2, Issue 6, 1996, Pages 709-728

Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

Author keywords

Crown ethers; Dialkylammonium salts; Hydrogen bonding; Molecular recognition; Pseudorotaxanes; Self assembly

Indexed keywords

DIALKYLAMMONIUM; GASPHASE; HEXAFLUOROPHOSPHATE SALT; HYDROGEN BONDING INTERACTIONS; INCLUSION COMPLEX; PSEUDOROTAXANES; SELF-ASSEMBLE; SELF-ASSEMBLING;

EID: 0037808071     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020616     Document Type: Article
Times cited : (339)

References (134)
  • 2
    • 0000769333 scopus 로고
    • (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Academic Press, London
    • a) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Academic Press, London, 1984, 261-335;
    • (1984) Inclusion Compounds , vol.2 , pp. 261-335
    • Goldberg, I.1
  • 3
  • 16
    • 0027919775 scopus 로고
    • b) J.-M. Lehn, Science 1993, 260, 1762-1763;
    • (1993) Science , vol.260 , pp. 1762-1763
    • Lehn, J.-M.1
  • 43
    • 0001035562 scopus 로고
    • and references therein
    • S. Misumi, Top. Curr. Chem. 1993, 165, 163-192 and references therein.
    • (1993) Top. Curr. Chem. , vol.165 , pp. 163-192
    • Misumi, S.1
  • 58
    • 84891314458 scopus 로고    scopus 로고
    • note
    • Pseudorotaxanes have been defined as inclusion complexes in which a thread-like molecule is encircled by one or more ringlike molecules in such a way that the two ends of the thread are projected away from the center of the ring. In a rotaxane (Latin rota, wheel; axis, axle), the two ends of the thread are terminated by bulky groups which do not allow the passage of the ring - thus, the two (or more) components are mutually interlocked. The prefix pseudo denotes that in a pseudorotaxane the two components are not interlocked, but instead are free to dissociate because the end groups are small enough to allow passage of the ring. See, for example, ref. [28].
  • 69
    • 33751156895 scopus 로고
    • For three recent representative examples, see
    • For three recent representative examples, see: e) E. Córdova, R. Bissell, A. E. Kaifer, J. Org. Chem. 1995, 60, 1033-1038;
    • (1995) J. Org. Chem. , vol.60 , pp. 1033-1038
    • Córdova, E.1    Bissell, R.2    Kaifer, A.E.3
  • 86
    • 84891333055 scopus 로고    scopus 로고
    • note
    • This situation may not be too surprising since the dialkylammonium ions are charged and need not be protonated by the matrix upon fast atom bombardment. Thus, peaks corresponding to the dialkylammonium ions and their (stronger) complexes may be expected to be more intense than those for protonated, but uncomplexed, crown ethers.
  • 88
    • 84891335907 scopus 로고    scopus 로고
    • note
    • 1H NMR timescale at 400 MHz.
  • 89
    • 84891328142 scopus 로고    scopus 로고
    • 3 are +0.19, -0.30, -0.25, and -0.23 ppm, respectively
    • 3 are +0.19, -0.30, -0.25, and -0.23 ppm, respectively.
  • 94
    • 77956813169 scopus 로고    scopus 로고
    • c and Δν is the limiting chemical shift difference (in Hz) between the coalescing signals in the absence of exchange
    • c and Δν is the limiting chemical shift difference (in Hz) between the coalescing signals in the absence of exchange.
  • 95
    • 84891308212 scopus 로고    scopus 로고
    • 2O present in the solvent - once the dialkylammonium ion center is encircled by the crown ether.
    • 2O present in the solvent - once the dialkylammonium ion center is encircled by the crown ether.
  • 105
    • 0023249018 scopus 로고
    • Polyamine/polyammonium polymers are known
    • Polyamine/polyammonium polymers are known: a) T. Perner, R. C. Schultz, Br. Polym. J. 1987, 19, 181-188;
    • (1987) Br. Polym. J. , vol.19 , pp. 181-188
    • Perner, T.1    Schultz, R.C.2
  • 107
    • 85023296576 scopus 로고
    • a determination of a different kind has been reported by
    • a determination of a different kind has been reported by J. C. Adrian, Jr., C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 678-680.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 678-680
    • Adrian Jr., J.C.1    Wilcox, C.S.2
  • 108
    • 49949144245 scopus 로고
    • The Gutmann donor number provides a semiquantitative measurement of the ability of a solvent to donate its electrons in a noncovalent bond
    • The Gutmann donor number provides a semiquantitative measurement of the ability of a solvent to donate its electrons in a noncovalent bond: a) V. Gutmann, E. Wychera, Inorg. Nucl. Chem. Lett. 1966, 2, 257-260;
    • (1966) Inorg. Nucl. Chem. Lett. , vol.2 , pp. 257-260
    • Gutmann, V.1    Wychera, E.2
  • 111
    • 84891284531 scopus 로고    scopus 로고
    • p
    • p.
  • 116
    • 0027375960 scopus 로고
    • It seems that from the recent number of publications dealing with significant heat capacity effects in host - guest chemistry, chemists should include this effect routinely in thermodynamic studies on such systems. When one is aware of the effect a nonnegligible heat capacity can have on a van't Hoff plot (i.e., curvature), one can see this effect in the literature for a number of plots - although the data points appear to be aligned along a curve, a straight line of best fit is used with a reasonably accurate "R" value. See, for example
    • It seems that from the recent number of publications dealing with significant heat capacity effects in host - guest chemistry, chemists should include this effect routinely in thermodynamic studies on such systems. When one is aware of the effect a nonnegligible heat capacity can have on a van't Hoff plot (i.e., curvature), one can see this effect in the literature for a number of plots - although the data points appear to be aligned along a curve, a straight line of best fit is used with a reasonably accurate "R" value. See, for example,: a) K. Araki, K. Inada, H. Otsuka, S. Shinkai, Tetrahedron 1993, 49, 9465-9478;
    • (1993) Tetrahedron , vol.49 , pp. 9465-9478
    • Araki, K.1    Inada, K.2    Otsuka, H.3    Shinkai, S.4
  • 122
    • 84891333924 scopus 로고    scopus 로고
    • b, δ = 3.45
    • b, δ = 3.45.
  • 127
    • 84891279279 scopus 로고    scopus 로고
    • 2 are +0.18, -0.03, -0.12, -0.31, and -0.43 ppm, respectively
    • 2 are +0.18, -0.03, -0.12, -0.31, and -0.43 ppm, respectively.
  • 133
    • 84891329026 scopus 로고    scopus 로고
    • 2+ dication
    • 2+ dication.
  • 134
    • 84871020737 scopus 로고
    • Versions 4.02 and 5.03 Siemens Analytical X-Ray Instruments, Madison, WI
    • G. M. Sheldrick, SHELXTL Versions 4.02 (1990) and 5.03 (1994), Siemens Analytical X-Ray Instruments, Madison, WI.
    • (1990) SHELXTL
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.