Structures of (3n-crown-n)-Phenol (n=4, 5, 6, 8) Host-Guest Complexes : Formation of a Uniquely Stable Complex for n=6 via Collective Intermolecular Interaction
The Journal of Physical Chemistry Letters Volume 3 Issue 10
Page 1414-1420
published_at 2012-05-17
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| File | |
| Title ( eng ) |
Structures of (3n-crown-n)-Phenol (n=4, 5, 6, 8) Host-Guest Complexes : Formation of a Uniquely Stable Complex for n=6 via Collective Intermolecular Interaction
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| Creator |
Kusaka Ryoji
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| Source Title |
The Journal of Physical Chemistry Letters
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| Volume | 3 |
| Issue | 10 |
| Start Page | 1414 |
| End Page | 1420 |
| 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”.
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| Keywords |
phenol
crown ethers
host-guest complex
molecular recognition
lock and key
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| Descriptions |
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).
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| NDC |
Chemistry [ 430 ]
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| Language |
eng
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| Resource Type | journal article |
| Publisher |
American Chemical Society
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| Date of Issued | 2012-05-17 |
| Rights |
Copyright (c) 2012 American Chemical Society
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| Publish Type | Author’s Original |
| Access Rights | open access |
| Source Identifier |
[DOI] 10.1021/jz300313d
[DOI] http://dx.doi.org/10.1021/jz300313d
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