Structural and conformational studies of alcohol, diol and methyl ether derivatives of dibenzo-14-crown-4. Implications for ligand and tecton design
- Authors
- Olsher, Uriel; Shoham, Gil; Dalley, N. Kent; Weining, Jiang; Luboch, Elzbieta; Yu, Zong-Yuan; Knobeloch, John M.; Lee, Jong Chan; Talanov, Vladimir S.; Bartsch, Richard A.
- Issue Date
- 1999
- Publisher
- Royal Society of Chemistry
- Citation
- JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, pp 2557 - 2564
- Pages
- 8
- Journal Title
- JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
- Start Page
- 2557
- End Page
- 2564
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/57648
- DOI
- 10.1039/A904180J
- ISSN
- 0300-9580
- Abstract
- Molecular structures are determined for six dibenzo-14-crown-4 derivatives that have one or two substituents on the central carbon(s) of the three-carbon bridge(s). The series of compounds includes three crown ether alcohols, one crown ether trans-diol, and two methoxy crown ether compounds. The crystal structures for these six crown ethers reveal that due to hydrogen-bonding and steric interactions, a hydroxy substituent is directed, at least partially, toward the crown ether cavity and an unusual intra- and intermolecular hydrogen bond network is formed between the hydroxy group protons and the ether oxygens of the crown ether ring. On the other hand, an ether group or a substituent with carbon as the first atom is oriented away from the polyether ring. The structure of sym-(methoxy)(methyl)dibenzo-14-crown-4 is markedly different from that of sym-(hydroxy)(methyl)dibenzo-14-crown-4 both in terms of the substituent orientation and very significant distortion from planarity of the four crown ether oxygens in the former. Support for an unusual conformation for sym-(methoxy)(methyl)dibenzo-14-crown-4 in solution is derived from 13C NMR measurements. Crown ether alcohols are hydrogen-bonding “tectons” that participate in strong, specific and directional intermolecular interactions.
- Files in This Item
- There are no files associated with this item.
- Appears in
Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
![qrcode](https://api.qrserver.com/v1/create-qr-code/?size=55x55&data=https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/57648)
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.