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ID 37977
file
creator
Kusaka, Ryoji
subject
phenol
crown ethers
host-guest complex
molecular recognition
lock and key
NDC
Chemistry
abstract
Structures of crown-phenol 1:1 host-guest complexes, 3n-crown-n [12C4(n=4), 15C5(n=5), 18C6(n=6), 24C8(n=8)], in the gas phase have been studied by various laser spectroscopic methods. The S1-S0 electronic spectra identified 3, 2, 1, and 2 isomers for the complexes of 12C4, 15C5, 18C6, and 24C8, respectively, suggesting that only 18C6-phenol forms one uniquely stable complex. The IR spectra in the phenolic OH and CH stretch regions indicate that these complexes form the O・・・HO hydrogen bond and the benzene ring is involved in the complex formation. Theoretical analysis with molecular mechanics and density functional theory calculations also supports one considerably stable isomer for 18C6-phenol. The most stable 18C6-phenol isomer is largely stabilized through collective intermolecular interaction consisting of O・・・HO hydrogen bond, CH・・・π, and O・・・HC(aromatic) so that phenol is inserted into the cavity of a particular conformation of 18C6 like a “lock and key”.
description
This is a preprint of an article published by American Chemical Society in The Journal of Physical Chemistry Letters, 2012, available online: http://pubs.acs.org/doi/abs/10.1021/jz300313d.
R.K. is supported by JSPS Research Fellowships for Young Scientists. T. E. acknowledges support from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) through a Grant-in-Aid for the Scientific Research on Priority Area “Molecular Science for Supra Functional Systems” (No. 477). Y. I. thanks the support of the JSPS through a Grant-in-Aid (No. 21350016).
journal title
The Journal of Physical Chemistry Letters
volume
Volume 3
issue
Issue 10
start page
1414
end page
1420
date of issued
2012-05-17
publisher
American Chemical Society
publisher doi
language
eng
nii type
Journal Article
HU type
Journal Articles
DCMI type
text
format
application/pdf
text version
author
rights
Copyright (c) 2012 American Chemical Society
relation is version of URL
http://dx.doi.org/10.1021/jz300313d
department
Graduate School of Science