Abstract
Research in the synthesis and study of molecular tweezers is an established and growing area of interest in the field of molecular recognition and inclusion. The work of Zimmermann has been of particular impact in this area. His contributions focus on a series of molecular tweezers which are achiral.1
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References
Zimmerman, S.C. Top. Curr. Chem. 1993, 165, 71.
Harmata, M.; Barnes, C.L. Tetrahedron Lett. 1990, 31, 1825.
Data on 3: mp > 300 °C; lH NMR (CDC13, 500 MHz) δ 7.70 (d, 2H, J = 8.3 Hz), 7.62 (d, 2H, J = 7.8 Hz), 7.54 (d, 2H, J = 8.4 Hz), 7.34, (t, 2H, J = 7 Hz), 7.28 (t, 2H, J = 7 Hz), 7.13 (d, 2H, J = 8 Hz), 6.75 (s, 2H), 5.37 (d, 2H, J = 6.4 Hz), 5.32 (d, 2H, J = 6.4 Hz), 3.61 (dd, 2H, J = 6.4, 16.2 Hz), 3.55 (dd, 2H, J = 6.4, 16.2 Hz), 3.02 (d 2H, J = 16.2 Hz), 2.81 (d, 2H, J = 16.2 Hz); 13C NMR (CDCl3, 125 MHz) δ 136.9, 134.9, 132.4, 131.8, 128.9, 128.4, 126.9, 126.3, 126.3, 126.1, 125.7, 125.2, 123.5, 122.5, 69.8, 69.3, 34.6, 32.7; HRMS exact mass calcd for C34H26O2: 466.1933, found 466.1927.
Data for 3/maleic anhydride: Formula: C34H26O2·C4H2O3; MW = 564.63 Space Group: P21/c; a = 7.1332(10)Å, b = 20.343(2)Å, c = 18.834(3)Å; V = 697.6(7)Å3; Z = 4; Dcalc = 1.393 Mg.m-3; mu = 0.09 mm-1; F(000)=1184; Radiation=MoKα (λ=0.70930Å); Temperature=-100(1)°C; Final R=0.037 for 3174 reflections with I>2.5σ(I).
Hunter, C.A. Angew. Chem. Int. Ed. Engl. 1993, 32, 1584.
Jones, G.B.; Chapman, B.J. Synthesis 1995, 475.
Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665.
Data for 3/p-chloronitrobenzene: Formula: C34H26O2·C6H4C1NO2; MW = 624.13 Space Group: P21/n; a = 20.188(3)Å, b = 7.342(4)Å, c = 20.991(3)Å; V = 2972.8(17)Å3; Z = 4; Dcalc = 1.395 Mg.m-3; mu = 0.18 mm-1; F(000)=1456; Radiation=MoKα (λ=0.70930Å); Temperature = 23(1)°C; Final R=0.101 for 1998 reflections with I>2.5σ(I).
Data for 3/1,3,5-trinitrobenzene: Formula: C34H26O2·2C6H3N3O6·0.5CHCl3; MW = 952.98 Space Group: P21/c; a = 13.326(3)Å, b = 17.834(2)Å, c = 18.314(4)Å; V = 4097.1(14)Å3; Z = 4; Dcalc = 1.545 Mg.m-3; mu = 0.20 mm-1; F(000)=1964; Radiation=MoKα (λ,=0.70930Å); Temperature =-100(1)°C; Final R=0.054 for 4190 reflections with I>2.5σ(I).
Solution binding studies were conducted by titration of TNB with the host at concentrations below which the host self-associated. The change in the chemical shift in the 1H NMR of the TNB as a function of host concentration was monitored and the data analyzed by a least squares fitting procedure.10
Wilcox, C.S.; Cowart, M.D. Tetrahedron Lett. 1986, 27, 5563.
We thank Mr. Sandy Pusalkar for obtaining this result.
Harmata, M.; Barnes, C.L. J. Am. Chem. Soc. 1990, 112, 5655.
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Pirkle, W.H.; Welch, C.J. J. Chromatogr. A 1994, 683, 347.
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Harmata, M., Kahraman, M., Tyagarajan, S., Barnes, C.L., Welch, C.J. (1998). Molecular Clefts Derived from Kagan’s Ether. Synthesis and Solid State Inclusion Complexes of a Chiral Molecular Tweezer. In: Coleman, A.W. (eds) Molecular Recognition and Inclusion. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5288-4_12
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DOI: https://doi.org/10.1007/978-94-011-5288-4_12
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