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  The Conformational Map of Volatile Anesthetics: Enflurane Revisited

Pérez, C., Caballero-Mancebo, E., Lesarri, A., Cocinero, E. J., Alkorta, I., Suenram, R. D., et al. (2016). The Conformational Map of Volatile Anesthetics: Enflurane Revisited. Chemistry – A European Journal, 22(28), 9804-9811. doi:10.1002/chem.201601201.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002A-E4E9-2 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002A-FB43-0
Genre: Journal Article

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http://dx.doi.org/10.1002/chem.201601201 (Publisher version)
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 Creators:
Pérez, Cristóbal1, 2, Author              
Caballero-Mancebo, Elena3, Author
Lesarri, Alberto3, Author
Cocinero, Emilio J.4, Author
Alkorta, Ibon5, Author
Suenram, Richard D.2, Author
Grabow, Jens-Uwe6, Author
Pate, Brooks H.2, Author
Affiliations:
1Structure 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              
2Department of Chemistry, University of Virginia, McCormick Rd., Charlottesville, Virginia 22904 (USA), ou_persistent22              
3Departamento de Química Física y Química Inorgánica, Universidad de Valladolid, 47011 Valladolid (Spain), ou_persistent22              
4Departamento de Química Física, Universidad del País Vasco, Ap. 644, 48080 Bilbao (Spain), ou_persistent22              
5Instituto de Química Médica, CSIC, Madrid (Spain), ou_persistent22              
6Institut für Physikalische Chemie und Elektrochemie, Lehrgebiet A, Gottfried-Wilhelm-Leibniz-Universität, Callinstrasse 3A, 30167 Hannover (Germany), ou_persistent22              

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Free keywords: ab initio calculations; halogenated ethers; rotational spectroscopy; supersonic jets; volatile anesthetics
 Abstract: Previous ambiguities in the conformational and structural landscape of the volatile anesthetic enflurane have been solved combining microwave spectroscopy in a jet expansion and ab initio calculations. The broadband (2–18 GHz) rotational spectra identified three different rotamers, sharing a common trans ether skeleton but differing in the ±gauche/trans position of the terminal chlorine atom. For each chlorine conformation two different gauche orientations were predicted for the opposite difluoromethyl group, but only one is experimentally observable due to collisional relaxation in the jet. The experimental dataset comprised nine different isotopologues (35Cl, 37Cl, 13C) and a large number (>6500) of rotational transitions. The inertial data provided structural information using the substitution and effective procedures. The structural preferences were rationalized with additional ab initio, natural-bond-orbital and non-covalent-interaction analysis, which suggest that plausible anomeric effects at the difluoromethyl group could be overridden by other intramolecular effects. The difluoromethyl orientation thus reflects a minimization of inter-fluorine repulsions while maximizing F⋅⋅⋅H attractive interactions. A comparison with previous electron diffraction and spectroscopic data in the gas and condensed phases finally resulted in a comprehensive description of this ether, completing a rotational description of the most common multi-halogenated anesthetics.

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Language(s): eng - English
 Dates: 2016-03-142016-06-022016-07-04
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201601201
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 22 (28) Sequence Number: - Start / End Page: 9804 - 9811 Identifier: ISSN: 0947-6539
CoNE: /journals/resource/954926979058