Noncovalent synthesis of donor/acceptor stacks

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5155-5158

  Colonna, Barbara ^a   Menzer, Stephan ^b   Raymo, Françisco M ^a   Stoddart, J Fraser ^a   Williams, David J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIMETHOXYBENZENE; ACRYLONITRILE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032537695     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00985-X     Document Type: Article

References (37)

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30. 8. This observation was reported as early as 1963, although the stoichiometry of the complex and its association constant were not determined at that time. See: Zweig, A. J. Phys. Chem. 1963, 67, 506-508.
31. 2 at 22°C.
32. 10. Connors, K.A. Binding Constants, Wiley, New York, 1987.
33. 11. TCNE was purified by crystallization from PhCl followed by sublimation. DMB was purified by crystallization from PhCl.
34. 2 = 0.160 for 723 independent observed reflections [I > 2σ(1), 2θ < 120°] and 91 parameters.
35. 13. The single crystal X-ray analysis of a 1:1 complex formed between TCNE and 5,8-dimethoxy-2,11-dithia[3.3]paracyclophane - i.e., a cyclophane incorporating, in one of its two para-phenylene rings, a pair of methoxyl substituents that are para to each other - shows a similar relative orientation of the TCNE acceptor and the para-dimethoxy-substituted donor. The mean planes of the two units are parallel to each other with interplanar and [centroid⋯centroid] separations of 3.15 and 3.10 Å, respectively. The angle subtended by the [O⋯O] axis of the donor and the [C=C] axis of the acceptor is 35°. See: Cohen-Addad, C.; Consigny, M.; D'Assenza, G., Baret, P. Acta Cryst. 1988, C44, 1924-1926.
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37. 2 = 0.271 for 2209 independent observed reflections [I > 2σ(I), 2θ ≤ 110°] and 249 parameters.