Topic
Acetonitrile
About: Acetonitrile is a research topic. Over the lifetime, 11298 publications have been published within this topic receiving 175275 citations. The topic is also known as: cyanomethane & ethyl nitrile.
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TL;DR: A series of stable organosuperbases were efficiently synthesized from N,N'-dialkylthioureas and 3-hydroxy-2-butanone and their basicities were measured in acetonitrile and the derivatives with tert-alkyl groups on the imino nitrogen were found to be more basic than the tBuP(1) (pyrr) phosphazene base in aconetitrile.
Abstract: A series of stable organosuperbases, N-alkyl- and N-aryl-1,3-dialkyl-4,5-dimethylimidazol-2-ylidene amines, were efficiently synthesized from N,N'-dialkylthioureas and 3-hydroxy-2-butanone and their basicities were measured in acetonitrile. The derivatives with tert-alkyl groups on the imino nitrogen were found to be more basic than the tBuP(1) (pyrr) phosphazene base in acetonitrile. The origin of the high basicity of these compounds is discussed. In acetonitrile and in the gas phase, the basicity of the alkylimino derivatives depends on the size of the substituent at the imino group, which influences the degree of aromatization of the imidazole ring, as measured by (13)C NMR chemical shifts or by the calculated ΔNICS(1) aromaticity parameters, as well as on solvation effects. If a wider range of imino-substituents, including electron-acceptor substituents, is treated in the analysis then the influence of aromatization is less predominant and the gas-phase basicity becomes more dependent on the field-inductive effect, polarizability, and resonance effects of the substituent.
62 citations
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TL;DR: In this paper, the physicochemical and structural properties of binary or ternary mixtures of 1- n -butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF 6 ])+ organic solvent were studied.
62 citations
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TL;DR: In this article, a simple and efficient method for the synthesis of β-hydroxy nitriles by the direct opening of 1,2-epoxides with KCN in acetonitrile, in the presence of metal salts, is described.
62 citations
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TL;DR: One-electron redox potentials of redox-active organic molecules for a spectrum of eight different functional groups in protic (water) and aprotic (acetonitrile, N,N-dimethylacetamide) solvents are estimated.
Abstract: We estimated one-electron reduction potentials of redox-active organic molecules for a spectrum of eight different functional groups (phenoxyl, p-benzoquinone, phenylthiyl, p-benzodithiyl, carboxyl, benzoyloxyl, carbthiyl, and benzoylthiyl) in protic (water) and aprotic (acetonitrile, N,N-dimethylacetamide) solvents. Electron affinities (EA) were evaluated in a vacuum with high level quantum chemical methods using Gaussian3-MP2 (G3MP2) and Becke 3 Lee, Yang, and Parr functional B3LYP with aug-cc-pVTZ basis set. To evaluate one-electron redox potentials, gas-phase free energies were combined with solvation energies obtained in a two-step computational approach. First, atomic partial charges were determined in a vacuum by the quantum chemical method B3LYP/6-31G(d,p). Second, solvation energies were determined, solving the Poisson equation with these atomic partial charges. Redox potentials computed this way, compared to experimental data for the 21 considered organic compounds in different solvents, yielded...
62 citations
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TL;DR: In this paper, the formation of protonated molecules (C2H4N+ cations), and a complex between acetonitrile and water (C 2H6NO+cations), is observed.
62 citations