Journal article
Coplanar Recognition by a Rebek Cleft Is Provided by Cooperative Structural Effects Involving a Combination of O−H···O, O−H···N, and C−H···O Forces
Organic letters, Vol.3(9), pp.1257-1260
05/01/2001
DOI: 10.1021/ol0156695
Abstract
(equation presented) Reaction of 2,7-di-tert-butyl-9,9-dimethyl-4,5-xanthenedicarboxylic acid (1), a Rebek cleft, with 1,2-trans-bis(2-pyridyl)ethylene (2) yields a three-component organic assembly, 2(1)·2 (3), of nanoscale dimensions that is held together by 10 cooperative 0-H⋯N, O-H⋯O, and C-H⋯O hydrogen bonds. The cleft adopts a planar conformation, by forming an intramolecular O-H⋯O hydrogen bond, which enables the host to recognize the guest in a coplanar orientation that facilitates the cooperativity displayed by the multiple forces.
Details
- Title: Subtitle
- Coplanar Recognition by a Rebek Cleft Is Provided by Cooperative Structural Effects Involving a Combination of O−H···O, O−H···N, and C−H···O Forces
- Creators
- Leonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294Michelle M Siebke - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294Jennifer L Reid - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.3(9), pp.1257-1260
- DOI
- 10.1021/ol0156695
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Language
- English
- Date published
- 05/01/2001
- Academic Unit
- Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
- Record Identifier
- 9984216673502771
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