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  The phenyl vinyl ether–methanol complex: a model system for quantum chemistry benchmarking

Bernhard, D., Dietrich, F., Fatima, M., Pérez, C., Gottschalk, H. C., Wuttke, A., et al. (2018). The phenyl vinyl ether–methanol complex: a model system for quantum chemistry benchmarking. Beilstein Journal of Organic Chemistry, 14, 1642-1654. doi:10.3762/bjoc.14.140.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0001-BCBF-5 Version Permalink: http://hdl.handle.net/21.11116/0000-0001-BCC1-1
Genre: Journal Article

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1860-5397-14-140.pdf (Publisher version), 5MB
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1860-5397-14-140.pdf
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This is an Open Access article under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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2018
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https://dx.doi.org/10.3762/bjoc.14.140 (Publisher version)
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 Creators:
Bernhard, D.1, Author
Dietrich, F.1, Author
Fatima, Mariyam2, 3, Author              
Pérez, C.2, 3, Author              
Gottschalk, H. C.4, Author
Wuttke, A.4, Author
Mata, R. A.4, Author
Suhm, M. A.4, Author
Schnell, M.2, 3, 5, Author              
Gerhards, M.1, Author
Affiliations:
1Fachbereich Chemie & Research Center Optimas, Technische Universität Kaiserslautern, ou_persistent22              
2Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society, ou_1938292              
3Deutsches Elektronen Synchrotron (DESY), ou_persistent22              
4Institut für Physikalische Chemie, Georg-August-Universität Göttingen, ou_persistent22              
5Institute of Physical Chemistry, Christian-Albrechts-Universität zu Kiel, ou_persistent22              

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Free keywords: dispersion interactions; IR spectroscopy; quantum-chemical calculations; rotational spectroscopy; structure determination; weak hydrogen bonds
 Abstract: The structure of the isolated aggregate of phenyl vinyl ether and methanol is studied by combining a multi-spectroscopic approach and quantum-chemical calculations in order to investigate the delicate interplay of noncovalent interactions. The complementary results of vibrational and rotational spectroscopy applied in molecular beam experiments reveal the preference of a hydrogen bond of the methanol towards the ether oxygen (OH∙∙∙O) over the π-docking motifs via the phenyl and vinyl moieties, with an additional less populated OH∙∙∙P(phenyl)-bound isomer detected only by microwave spectroscopy. The correct prediction of the energetic order of the isomers using quantum-chemical calculations turns out to be challenging and succeeds with a sophisticated local coupled cluster method. The latter also yields a quantification as well as a visualization of London dispersion, which prove to be valuable tools for understanding the role of dispersion on the docking preferences. Beyond the structural analysis of the electronic ground state (S0), the electronically excited (S1) state is analyzed, in which a destabilization of the OH∙∙∙O structure compared to the S0 state is observed experimentally and theoretically.

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Language(s): eng - English
 Dates: 2018-03-162018-06-022018-07-02
 Publication Status: Published online
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.3762/bjoc.14.140
 Degree: -

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Project name : The authors thank the Deutsche Forschungsgemeinschaft (DFG, Ge 961/9-1, Schn 1280/4-1, Su 121/5-1, and Ma 5063/3-1) for financial support in context of the priority program SPP 1807 on the Control of London dispersion interactions in molecular chemistry. M.F. acknowledges support from the Hamburg Inter- national Max Planck Research School UFAST. This work is part of the Ph.D. theses of D.B., M.F., H.G. and A.W.
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Title: Beilstein Journal of Organic Chemistry
Source Genre: Journal
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Publ. Info: Frankfurt, Germany : Beilstein-Institut
Pages: 13 Volume / Issue: 14 Sequence Number: - Start / End Page: 1642 - 1654 Identifier: ISSN: 1860-5397
CoNE: /journals/resource/1000000000021310