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Tytuł pozycji:

Determination of the semiexperimental equilibrium structure of 2-acetylthiophene in the presence of methyl internal rotation and substituent effects compared to thiophene.

Tytuł:
Determination of the semiexperimental equilibrium structure of 2-acetylthiophene in the presence of methyl internal rotation and substituent effects compared to thiophene.
Autorzy:
Dindić C; Institute of Physical Chemistry, RWTH Aachen University, Landoltweg 2, Aachen 52074, Germany.
Ludovicy J; Institute of Physical Chemistry, RWTH Aachen University, Landoltweg 2, Aachen 52074, Germany.
Terzi V; Institute of Physical Chemistry, RWTH Aachen University, Landoltweg 2, Aachen 52074, Germany.
Lüchow A; Institute of Physical Chemistry, RWTH Aachen University, Landoltweg 2, Aachen 52074, Germany.
Vogt N; Section of Chemical Information Systems, University of Ulm, Albert-Einstein-Allee 47, Ulm 89081, Germany.; Department of Inorganic Chemistry, Lomonosov Moscow State University, Moscow 119991, Russian Federation.
Demaison J; Section of Chemical Information Systems, University of Ulm, Albert-Einstein-Allee 47, Ulm 89081, Germany.
Nguyen HVL; Univ Paris Est Creteil and Université de Paris, CNRS, LISA, Créteil 94010, France.; Institut Universitaire de France (IUF), Paris cedex 05 75231, France. .
Źródło:
Physical chemistry chemical physics : PCCP [Phys Chem Chem Phys] 2022 Feb 09; Vol. 24 (6), pp. 3804-3815. Date of Electronic Publication: 2022 Feb 09.
Typ publikacji:
Journal Article
Język:
English
Imprint Name(s):
Original Publication: Cambridge [England] : Royal Society of Chemistry, c1999-
MeSH Terms:
Microwaves*
Thiophenes*
Fourier Analysis ; Molecular Conformation
Substance Nomenclature:
0 (Thiophenes)
5ASO208T20 (2-acetylthiophene)
Entry Date(s):
Date Created: 20220127 Date Completed: 20220211 Latest Revision: 20220211
Update Code:
20240105
DOI:
10.1039/d1cp04478h
PMID:
35084004
Czasopismo naukowe
The microwave spectra of thiophene and 2-acetylthiophene were recorded in the frequency range from 2 to 40 GHz using two molecular jet Fourier transform microwave spectrometers. For 2-acetylthiophene, two conformers with a syn and an anti orientation of the S1-C2 and C6O bonds (with respect to the C2-C6 bond) were identified, and the syn -conformer was more stable. The spectra of the 34 S- and 13 C-isotopologues of syn -2-acetylthiophene were also assigned, and the semiexperimental equilibrium structure could be determined. Compared to thiophene, at the substitution position, the S1-C2 and C2C3 bond lengths both increase by about 0.007 Å, and the bond angle S1-C2C3 decreases by 0.06°, noticeably larger than the experimental uncertainties. A-E torsional splittings were observed due to internal rotation of the methyl group hindered by a barrier height of 330.187(35) and 295.957(17) cm -1 for the syn -conformer and the anti -conformer, respectively. Geometry and internal rotation parameters are compared with those of related thiophene derivatives, as well as those of furan and 2-acetylthiophene to gain a better understanding of structure determination in the presence of methyl internal rotation.

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