Relevant bibliographies by topics / Nitroalkane proton transfer

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Academic literature on the topic 'Nitroalkane proton transfer'

Author: Grafiati
Published: 4 June 2021
Last updated: 15 February 2022

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Journal articles on the topic "Nitroalkane proton transfer"

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Major, D. T., A. Heroux, A. M. Orville, M. P. Valley, P. F. Fitzpatrick, and J. Gao. "Differential quantum tunneling contributions in nitroalkane oxidase catalyzed and the uncatalyzed proton transfer reaction." Proceedings of the National Academy of Sciences 106, no. 49 (November 19, 2009): 20734–39. http://dx.doi.org/10.1073/pnas.0911416106.

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2

Ando, Kenichi, Yu Shimazu, Natsuko Seki, and Hiroshi Yamataka. "Kinetic Study of Proton-Transfer Reactions of Phenylnitromethanes. Implication for the Origin of Nitroalkane Anomaly." Journal of Organic Chemistry 76, no. 10 (May 20, 2011): 3937–45. http://dx.doi.org/10.1021/jo200383f.

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Galezowski, Wlodzimierz, Iwona Grzeskowiak, and Arnold Jarczewski. "Article." Canadian Journal of Chemistry 77, no. 5-6 (June 1, 1999): 1042–49. http://dx.doi.org/10.1139/v99-093.

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The rates of proton transfer reactions between C-acids of different types such as 1-(4-nitrophenyl)-1-nitroalkanes, 4-nitrophenylcyanomethanes, and 2,4,6-trinitrotoluene, and organic bases such as 1,1,3,3-tetrametylguanidine, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), and tri-n-butylamine have been measured in acetonitrile at pseudo-first-order conditions. A general equation for the rates of proton transfer reactions between C-acids and bases with product existing in two forms, ions and ion pairs, has been derived and its applicability tested. The equation works well except for reactions of 1-(4-nitrophenyl)-1-nitroalkanes with guanidines for which the second-order rate constant is diminished with concentration of guanidinium cation, while tetrabutylammonium salts accelerate the reactions. Possible reasons for this are discussed.Key words: proton transfer, kinetic study, ion pairs, C-acids, organic bases, acetonitrile, salt effect.
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Ponec, Robert. "Molecular Basis of LFER. Simple Model for the Estimation of Brønsted Exponent in Acid-Base Catalysis." Collection of Czechoslovak Chemical Communications 69, no. 12 (2004): 2121–33. http://dx.doi.org/10.1135/cccc20042121.

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A simple model was proposed allowing to estimate the Brønsted exponents in acid-base catalysis on the basis of the pK values of the species participating in the proton transfer process. The approach was tested using the experimental data on the basically catalyzed halogenation of carbonyl compounds and on the proton removal from nitroalkanes. It has been shown that the model is able to reproduce the Brønsted exponents not only in the case of "ordinary" Brønsted plots with the slope within the expected range 0-1 but also for unusual plots with negative slopes. In addition, the proposed model opens the possibility of calculation of the activation energies of a given proton transfer reaction and also provides straightforward theoretical justification for the validity of the Hammond postulate in these reactions.
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Sato, Makoto, Yutaka Kitamura, Nobuyoshi Yoshimura, and Hiroshi Yamataka. "Proton-Transfer Reactions of Nitroalkanes: The Role ofaci-Nitro Species." Journal of Organic Chemistry 74, no. 3 (February 6, 2009): 1268–74. http://dx.doi.org/10.1021/jo8023939.

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6

Galezowski, Wlodzimierz, and Arnold Jarczewski. "Kinetics, isotope effects of the reaction of 1-(4-nitrophenyl)-1-nitroalkanes with DBU in tetrahydrofuran and chlorobenzene solvents." Canadian Journal of Chemistry 68, no. 12 (December 1, 1990): 2242–48. http://dx.doi.org/10.1139/v90-345.

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The kinetics of the reaction of[Formula: see text](R = Me, Et, i-Pr; NPNE, NPNP, MNPNP respectively; L is H or D) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) base in tetrahydrofuran (THF) and chlorobenzene (CB) solvents are reported. The products of these proton transfer reactions are ion pairs absorbing at λmax = 460–480 nm. The equilibrium constants in THF were [Formula: see text]and in CB [Formula: see text]for NPNE, NPNP, MNPNP respectively. The thermodynamic parameters of the reactions are also quoted. The substrate reacts with DBU in both THF and CB solvents in a normal second-order proton transfer reaction. In the case of deuteron transfer, isotopic D/H exchange is much faster than internal return. The reactions show low values of enthalpy of activation ΔH* = 14.3, 18.1, 24.2 and 13.0, 15.1, 18.6 kJmol−1 for NPNE, NPNP, and MNPNP in THF and CB respectively, and large negative entropies of activation −ΔS* = 141, 139, 146; 140, 146, 160 J mol−1 deg−1 for the same sequence of substrates and solvents. The kinetic isotope effects are large, (kH/kD)20°c = 12.2, 13.0, 10.1; 12.9, 12.0, 10.2 for the above sequence of substrates and solvents, and show no difference with changes in either steric hindrance of the C-acids or polarity of the solvents. Keywords: proton transfer, kinetic isotope effect.
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7

Grzeskowiak, Iwona, Wtodzimierz Galezowski, and Arnold Jarczewski. "Kinetic study of the proton transfer reaction between 1-nitro-1-(4-nitrophenyl)alkanes and TBD and MTBD bases in acetonitrile solvent." Canadian Journal of Chemistry 79, no. 7 (July 1, 2001): 1128–34. http://dx.doi.org/10.1139/v01-093.

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The rates of proton transfer reactions between C-acids of the series of nitroalkanes with increasing bulk of R = H, Me, Et, i-Pr substituent as: 4-nitrophenylnitromethane (0), 1-(4-nitrophenyl)-1-nitroethane (1), 1-(4-nitrophenyl)-1-nitropropane (2), 2-methyl-1-(4-nitrophenyl)-1-nitropropane (3) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) have been measured in acetonitrile at pseudo-first-order conditions. The product of the proton transfer reaction with MTBD in acetonitrile is dissociated into free ions while that of the TBD reaction is composed of a comparable amount of ions and ion pairs. The second-order rate constants (k2H) for these bases of almost equal strength in acetonitrile (pKa = 24.70, 24.97 for MTBD and TBD) and C-acids 1, 2, and 3 are: 317, 86, 7.6 dm3 mol–1 s–1; and 15 200, 5300, 1100 dm3 mol–1 s–1, respectively. The appropriate primary deuterium kinetic isotope effects (kH/kD) are 12.5, 10.8, 6.9; and 9.9, 11.2, 12.6. The influence of steric hindrance brought by reacting C-acids and bases is discussed. The different structure of the transition states and the products as mono- and double-hydrogen bonded complexes for these series of C-acids and MTBD and TBD bases is manifested by a distinct reaction mechanism which we attempt to explain.Key words: proton transfer, kinetic study, C-acids, organic bases, acetonitrile, kinetic isotope effects.
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8

Galezowski, Wlodzimierz, and Arnold Jarczewski. "Study of the dissociation of the products of some proton transfer reactions in acetonitrile solvent." Canadian Journal of Chemistry 70, no. 3 (March 1, 1992): 935–42. http://dx.doi.org/10.1139/v92-126.

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The conductometric study of the products of the proton transfer reactions of C-acids (nitriles, nitroalkanes, and 2,4,6-trinitrotoluene) with the strong amine bases (1,1,3,3-tetramethylguanidine (TMG), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,8-bis(dimethylamino)naphthalene (DMAN), and piperidine) in acetonitrile shows their large degree of dissociation into free ions. The dissociation constant values have been estimated at 25 °C to be larger than 1 × 10−4 M. This weakens the formalism commonly accepted in spectrophotometric kinetic studies of these systems of reactions, based on the assumption that the product is an ion pair. Spectrophotometric equilibrium and kinetic measurements provided evidence that reverse reaction is a second-order process (pseudo-first order because cation concentration is controlled by side reactions). The influence of the common cation (TMGH+) on the equilibria of the proton abstraction from 2-methyl-1-(4-nitrophenyl)-1-nitropropane and 4-nitrophenylcyanomethane with TMG base in acetonitrile at 25 °C was examined and was found to be compatible with the assumption of large dissociation of the reaction product for free ions. "Equilibrium constants" estimated by the Benesi and Hildebrand method (which assumes an ion-pair product) decreased with increasing concentration of added TMGH+ cation, but these "equilibrium constants" multiplied by [TMGH+] are constant. The observed pseudo-first-order rate constants of the proton transfer reaction, measured at large excess of the base over C-acid, grow with the cation concentration due to the increase of the backward reaction rate. The concentration of added common cation shows a negligible influence on the observed rate constants of deuteron transfer reaction. Thus, as a result of side reactions, in which extra amounts of cation are formed, some second-order rate constants [Formula: see text] and also kinetic isotope effects (KIEs) [Formula: see text] that have been measured in acetonitrile can be substantially overestimated. Keywords: ion-pair dissociation, proton transfer reactions, kinetic isotope effects.
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9

Binkowska, Iwona, Włodzimierz Gałęzowski, and Arnold Jarczewski. "Equilibrium and kinetic study of the proton transfer reactions between nitroalkanes and strong organic bases — phosphazenes in tetrahydrofuran solvent." Open Chemistry 8, no. 3 (June 1, 2010): 582–86. http://dx.doi.org/10.2478/s11532-010-0044-9.

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AbstractProton transfer reactions rates between carbon acids 1-nitro-1-(4-nitrophenyl)ethane (NPNE), 2-methyl-1-nitro-1-(4-nitrophenyl)propane (MNPNP)) and phosphazenes (BEMP, BTPP, P1-t-Oct) in tetrahydrofuran have been measured, and the activation parameters were determined. The results are compared with those previously obtained for P1-t-Bu phosphazene, guanidines and amidines.
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10

Zhao, Yixing, Yun Lu, and Vernon D. Parker. "Proton-Transfer Reactions between Nitroalkanes and Hydroxide Ion under Non-Steady-State Conditions. Apparent and Real Kinetic Isotope Effects." Journal of the American Chemical Society 123, no. 8 (February 2001): 1579–86. http://dx.doi.org/10.1021/ja003607o.

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Dissertations / Theses on the topic "Nitroalkane proton transfer"

1

Li, Zhao. "The Kinetics and Mechanisms of Some Fundamental Organic Reactions of Nitro Compounds." DigitalCommons@USU, 2012. https://digitalcommons.usu.edu/etd/1407.

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The central topic of this dissertation is to seek the answer to the question: Is the single transition state model appropriate for (1) the proton transfer reactions of nitroalkanes and (2) the aromatic nucleophilic reactions of trinitroarenes? If not, what are the real mechanisms? This objective has been accomplished by careful kinetic and mechanistic studies which take advantage of modern digital acquisition of absorbance - time data, combined with extensive new data analysis of results from pseudo-first-order kinetic measurements. Several new analysis procedures for pseudo-first-order kinetics that are capable of distinguishing between single-step and multi-step mechanisms have been introduced and intensively confirmed during the application in the kinetic study of the target reactions. The procedures include (1) half-life dependence of apparent rate constant, (2) sequential linear pseudo-first-order correlation, (3) approximate instantaneous rate constant analysis, and (4) time-dependent apparent kinetic isotope effects. Various conventional and nonconventional pseudo-first-order kinetic analyses of the reactions of nitroalkanes in aqueous solutions revealed that the reactions are complex and involve kinetically significant intermediates. The spectral evidence for the formation of reactive intermediates was obtained by carrying out the kinetic experiments at the isosbestic points where changes in reactant and product absorbance cancel. The apparent deuterium kinetic isotope effects studies indicated that the deuterium kinetic isotope effects are not associated with the formation of the intermediates. The observations of anomalous Brønsted exponents previously found for this reaction series could be rationalized well with the complex mechanisms proposed in this work, which indicate that the nitroalkane anomaly does not exist, but arises from an interpretation based upon the incorrect assumption that the reactions follow a simple one-step mechanism. Simulations revealed that the generally accepted competitive mechanism was not appropriate to describe the Meisenheimer complex formation during the reaction of 2,4,6-trinitroanisole with methoxide ion in methanol. This conclusion is supported by the conventional pseudo-first-order kinetic analysis. A reversible consecutive mechanism that accounts for the kinetic behavior has been proposed, which involves an intermediate dianion complex that is formed reversibly from the initial 1,3-σ-complex, and then eliminates methoxide ion to form the 1,1-σ-complex product.
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