A dipole moment study of 2-benzoylpyrroles, di-(2-pyrryl)ketones and their sulphur analogues

Lumbroso, H.; Liégeois, Ch.; Pappalardo, Giuseppe; Andrieu, C. G.

doi:10.1016/0022-2860(84)80246-x

Cited by 17 publications

(9 citation statements)

References 34 publications

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“…(1-Methylpyrrol-2-yl)phenylmethanethione (2a) [12] 3073w, 1589m, 1505s, 1442s, 1406vs, 1336vs, 1240vs, 1173m, 1037s, 1046m Synthesis of Heteroaromatic Thioketones 2j-k. The bis(pyrrol-2-yl) and bis(N-methylpyrrol-2-yl)thioketones 2j and 2k were prepared by treatment of pyrrol or N-methylpyrrol with thiophosgene in the presence of triethylamine according to the literature procedure [11].…”

Section: Synthesis Of Heteroaromatic Thioketones 2a-imentioning

confidence: 99%

Hetaryl Thioketones: Synthesis and Selected Reactions

Mlostoń

Urbaniak

Gebicki

et al. 2014

Heteroatom Chemistry

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A series of phenyl/hetaryl and bishetaryl thioketones have been prepared via oxygen/sulfur exchange of the corresponding ketones by treatment with Lawesson's reagent. The nonsymmetrical ketones were conveniently accessible via the reactions of lithiated furan, thiophene, and selenophene with N,N-dimethylbenzamide and hetarylcarboxamides, respectively, whereas the symmetrical ketones were obtained by treatment of ethyl N,N-dimethylcarbamate with 2 equiv of lithiated heterocycles. Under typical conditions, selected examples of the hetaryl thioketones were oxidized selectively to give thiocarbonyl S-oxides (sulfines). Reactions with diazomethane at -65°C yielded 1,3-dithiolanes in a regioselective manner and hetero-Diels-Alder reactions of 2-thienyl substituted thioketones with dimethyl acetylenedicarboxylate yielded the corresponding 7H-thieno [2,3-c]

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Section: Synthesis Of Heteroaromatic Thioketones 2a-imentioning

confidence: 99%

Hetaryl Thioketones: Synthesis and Selected Reactions

Mlostoń

Urbaniak

Gebicki

et al. 2014

Heteroatom Chemistry

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“…In the case of 1a in benzene solution, its dipole moment is consistent with a mixture of cc-conformer and mixed conformers, with the latter being more abundant (73 %) [11]. Dipole moment measurements also show that the molecules of 4a and 4b tend to adopt the cc-conformation in several nonpolar solvents [12]. The X-ray analysis of crystal 2a indicates that the S atoms are always on the same side of the carbonyl group, and therefore, the cc-conformer of 2a seems to display an attractive interaction between sulfur and oxygen [13].…”

Section: Introductionmentioning

confidence: 98%

“…For some of the diheteroaryl ketones and thioketones considered here, their conformational behavior has previously been studied experimentally [10][11][12][13]. From dipole moment measurements, it is inferred that the cc-conformation is preferred for 2a [10].…”

Section: Introductionmentioning

confidence: 99%

Conformers of diheteroaryl ketones and thioketones: a quantum chemical study of their properties and fundamental intramolecular energetic effects

Matczak

Domagała

2015

Struct Chem

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The conformational behavior of ten diheteroaryl ketones and thioketones is investigated using various quantum chemical methods. These ketones and thioketones are formed by the disubstitution of formaldehyde and thioformaldehyde with such a heteroaryl group as 2-furanyl, 2-thiophenyl, 2-selenophenyl, 2-pyrrolyl or 1-methyl-2-pyrrolyl. For these compounds, their conformational preference and the energetic ordering of their conformers are determined at the MP2 and B3LYP levels of theory. Energetic barriers resulting from the interconversion between conformations are also estimated. The natural bond orbital (NBO) and interacting quantum atoms (IQA) methods are used to study fundamental intramolecular energetic effects influencing the stability of individual conformers. The results of the two methods indicate the great significance of the effect associated with electron delocalization (in the form of either NBO donor-acceptor interactions or the IQA interatomic exchange-correlation interaction energy) in governing the conformational behavior of the investigated diheteroaryl ketones and thioketones.

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“…The ligand 2-benzoylpyrrole (2-BZPH) was prepared according to a published procedure [14,15]. Spectroscopic IR, NMR, and melting point, 78°C, agree with reported values.…”

Section: Methodsmentioning

confidence: 93%