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Journal articles on the topic 'Mechanisms of organic reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Liu, Qiang, Xufang Liu, and Bin Li. "Base-Metal-Catalyzed Olefin Isomerization Reactions." Synthesis 51, no. 06 (February 19, 2019): 1293–310. http://dx.doi.org/10.1055/s-0037-1612014.

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The catalytic olefin isomerization reaction is a highly efficient and atom-economic transformation in organic synthesis that has attracted tremendous attention both in academia and industry. Recently, the development of Earth-abundant metal catalysts has received growing interest owing to their wide availability, sustainability, and environmentally benign nature, as well as the unique properties of non-precious metals. This review provides an overview of a broad range of base-metal-catalyzed olefin isomerization reactions categorized according to their different reaction mechanisms.1 Introduction2 Base-Metal-Catalyzed Olefin Isomerization Reactions3 Base-Metal-Catalyzed Cycloisomerization Reactions4 Conclusion

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2

Rakovsky, Slavcho, Metody Anachkov, Mikhail Belitskii, and Gennady Zaikov. "Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes." Chemistry & Chemical Technology 10, no. 4s (December 25, 2016): 531–51. http://dx.doi.org/10.23939/chcht10.04si.531.

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The review, based on 92 references, is focused on degradation of organics by ozonation and it comprises various classes of oxygen-containing organic compounds – alcohols, ketones, ethers and hydroxybenzenes. The mechanisms of a multitude of ozone reactions with these compounds in organic solvents are discussed in details, presenting the respective reaction schemes. The corresponding kinetic parameters are given and some thermodynamic parameters are also listed. The dependences of the kinetics and the mechanism of the ozonation reactions on the structure of the compounds, on the medium and on the reaction conditions are revealed. Various possible applications of ozonolysis are specified and discussed. All these reactions have practical importance for the protection of the environment.

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3

Daley, Ryan A., and Joseph J. Topczewski. "Aryl-Decarboxylation Reactions Catalyzed by Palladium: Scope and Mechanism." Synthesis 52, no. 03 (December 13, 2019): 365–77. http://dx.doi.org/10.1055/s-0039-1690769.

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Palladium-catalyzed cross-couplings and related reactions have enabled many transformations essential to the synthesis of pharmaceuticals, agrochemicals, and organic materials. A related family of reactions that have received less attention are decarboxylative functionalization reactions. These reactions replace the preformed organometallic precursor (e.g., boronic acid or organostannane) with inexpensive and readily available carboxylic acids for many palladium-catalyzed reactions. This review focuses on catalyzed reactions where the elementary decarboxylation step is thought to occur at a palladium center. This review does not include decarboxylative reactions where decarboxylation is thought to be facilitated by a second metal (copper or silver) and is specifically limited to (hetero)arenecarboxylic acids. This review includes a discussion of oxidative Heck reactions, protodecarboxylation reactions, and cross-coupling reactions among others.1 Introduction2 Oxidative Heck Reactions3 Protodecarboxylation Reactions4 Cross-Coupling Reactions5 Other Reactions6 Conclusion

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4

Miller, Bernard. "Advanced Organic Chemistry: Reactions and Mechanisms." Journal of Chemical Education 76, no. 3 (March 1999): 320. http://dx.doi.org/10.1021/ed076p320.2.

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5

Rosen, William M. "Advanced organic chemistry: Reactions and mechanisms." Concepts in Magnetic Resonance 10, no. 6 (1998): 369. http://dx.doi.org/10.1002/(sici)1099-0534(1998)10:6<369::aid-cmr4>3.0.co;2-v.

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6

THIBBLIN, A. "ChemInform Abstract: Elimination Reactions (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145330.

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7

Zuman, Petr. "Electrochemical Reactions and Mechanisms in Organic Chemistry." Microchemical Journal 73, no. 3 (December 2002): 367–68. http://dx.doi.org/10.1016/s0026-265x(02)00025-5.

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8

BOWMAN, W. R. "ChemInform Abstract: Radical Reactions (Organic Reaction Mechanisms)." ChemInform 25, no. 13 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199413284.

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9

RHODES, C. J. "ChemInform Abstract: Radical Reactions (Organic Reaction Mechanisms)." ChemInform 25, no. 13 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199413285.

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10

Long, Fengqin, Zheng Chen, Keli Han, Lu Zhang, and Wei Zhuang. "Differentiation between Enamines and Tautomerizable Imines Oxidation Reaction Mechanism using Electron-Vibration-Vibration Two Dimensional Infrared Spectroscopy." Molecules 24, no. 5 (March 1, 2019): 869. http://dx.doi.org/10.3390/molecules24050869.

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Intermediates lie at the center of chemical reaction mechanisms. However, detecting intermediates in an organic reaction and understanding its role in reaction mechanisms remains a big challenge. In this paper, we used the theoretical calculations to explore the potential of the electron-vibration-vibration two-dimensional infrared (EVV-2DIR) spectroscopy in detecting the intermediates in the oxidation reactions of enamines and tautomerizable imines with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). We show that while it is difficult to identify the intermediates from their infrared and Raman signals, the simulated EVV-2DIR spectra of these intermediates have well resolved spectral features, which are absent in the signals of reactants and products. These characteristic spectral signatures can, therefore, be used to reveal the reaction mechanism as well as monitor the reaction progress. Our work suggests the potential strength of EVV-2DIR technique in studying the molecular mechanism of organic reactions in general.

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11

Humeres, Eduardo. "Mechanisms of Water Catalysed Reactions." Molecules 5, no. 12 (March 22, 2000): 307–8. http://dx.doi.org/10.3390/50300307.

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12

Aghahosseini, Hamideh, Ali Ramazani, Farideh Gouranlou, and Sang Woo Joo. "Nanoreactors Technology in Green Organic Synthesis." Current Organic Synthesis 14, no. 6 (September 28, 2017): 810–64. http://dx.doi.org/10.2174/1570179413666161008200641.

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Background: Nanoreactors technology represents a promising tool for efficient and selective organic synthesis typically under “green” and sustainable reaction conditions. These structures with generating a confined reaction environment to accommodate that both reactants and catalysts can change the reaction pathways and induce new activities and selectivities. Objective: The paper reviews literature examples in which nanoreactors were employed in various types of organic and metal catalyzed reactions including multicomponent reactions, palladium-catalyzed coupling reactions, olefin metathesis, aza-Cope rearrangement, allylic alcohol isomerization, cyclization reactions, ring opening reactions, halogenation reactions, hydrolysis reactions, hydroformylation reactions, cascade reactions, addition reactions, oxidation reactions and reduction reactions. The reactions' survey is accompanied with the explanation of structure and performance of nanoreactors that are applied there. Conclusion: The availability of comprehensive information about the role of nanoreactors technology in green organic synthesis and investigation of different aspects of them such as their structures, mechanisms and synthetic utility can assist researchers in designing the greener approaches in organic synthesis.

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13

Ormazábal-Toledo, Rodrigo, and Renato Contreras. "Philicity and Fugality Scales for Organic Reactions." Advances in Chemistry 2014 (August 18, 2014): 1–13. http://dx.doi.org/10.1155/2014/541547.

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Theoretical scales of reactivity and selectivity are important tools to explain and to predict reactivity patterns, including reaction mechanisms. The main achievement of these efforts has been the incorporation of such concepts in advanced texts of organic chemistry. In this way, the modern organic chemistry language has become more quantitative, making the classification of organic reactions an easier task. The reactivity scales are also useful to set up a number of empirical rules that help in rationalizing and in some cases anticipating the possible reaction mechanisms that can be operative in a given organic reaction. In this review, we intend to give a brief but complete account on this matter, introducing the conceptual basis that leads to the definition of reactivity indices amenable to build up quantitative models of reactivity in organic reactions. The emphasis is put on two basic concepts describing electron-rich and electron-deficient systems, namely, nucleophile and electrophiles. We then show that the regional nucleophilicity and electrophilicity become the natural descriptors of electrofugality and nucleofugality, respectively. In this way, we obtain a closed body of concepts that suffices to describe electron releasing and electron accepting molecules together with the description of permanent and leaving groups in addition, nucleophilic substitution and elimination reactions.

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14

Bai, Chang, Bing Tian, Tian Zhao, Qing Huang, and Zhi Wang. "Cyclodextrin-Catalyzed Organic Synthesis: Reactions, Mechanisms, and Applications." Molecules 22, no. 9 (September 7, 2017): 1475. http://dx.doi.org/10.3390/molecules22091475.

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15

DENNIS, N. "ChemInform Abstract: Addition Reactions: Cycloaddition (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145332.

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16

Berger, Daniel J. "Advanced Organic Chemistry: Reactions and Mechanisms (Miller, Bernard)." Journal of Chemical Education 75, no. 12 (December 1998): 1558. http://dx.doi.org/10.1021/ed075p1558.

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17

Breinbauer, R. "The Investigation of Organic Reactions and their Mechanisms." Synthesis 2007, no. 9 (May 2007): 1438. http://dx.doi.org/10.1055/s-2007-980323.

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18

Ciaccia, Maria, and Stefano Di Stefano. "Mechanisms of imine exchange reactions in organic solvents." Organic & Biomolecular Chemistry 13, no. 3 (2015): 646–54. http://dx.doi.org/10.1039/c4ob02110j.

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19

DENNIS, N. "ChemInform Abstract: Addition Reactions: Cycloaddition (Organic Reaction Mechanisms)." ChemInform 25, no. 13 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199413290.

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20

Chirkina, E. A., L. B. Krivdin, A. G. Mal´kina, and B. A. Trofimov. "Quantum chemical study of mechanisms of organic reactions." Russian Chemical Bulletin 64, no. 3 (March 2015): 511–17. http://dx.doi.org/10.1007/s11172-015-0894-6.

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21

Galloway, Kelli R., Min Wah Leung, and Alison B. Flynn. "Patterns of reactions: a card sort task to investigate students’ organization of organic chemistry reactions." Chemistry Education Research and Practice 20, no. 1 (2019): 30–52. http://dx.doi.org/10.1039/c8rp00120k.

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Research has shown that within a traditional organic chemistry curriculum, organic chemistry students struggle to develop deep conceptual understanding of reactions and attribute little meaning to the electron-pushing formalism. At the University of Ottawa, a new curriculum was developed for organic chemistry in which students are taught the language of the electron-pushing formalism prior to learning about specific reactions. Reactions are then organized by governing pattern of mechanism rather than by functional group and are taught in a gradient of complexity. To investigate how students are making connections across reactions within the new curriculum, a card sort task was developed. The card sort task consisted of 25 cards, each depicting the reactants and solvent for a reaction taught during the two-semester organic chemistry sequence. The first part of the task asked participants to sort 15 of 25 cards into categories. Then, participants were given the 10 remaining cards to incorporate into categories with the previous 15. Participants were asked to explain the characteristics of each category and their sorting process. Students (N= 16) in an organic chemistry course were interviewed while enrolled in the second semester course. We analyzed the students’ sorts based on which cards were sorted frequently together, the underlying characteristics used to form the categories, and the participants’ sorting processes. Participants created categories based on different levels of interpreting the reactions on the cards, with levels ranging from recognizing identical structural features to identifying similar types of mechanisms. Based on this study, if we want students to develop mechanistic thinking, we think students need to be more explicitly directed to the patterns present in organic reaction mechanisms and given opportunities to uncover and identify patterns on their own, during both summative and formative assessments.

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22

Wu, Yan-Chen, Ren-Jie Song, and Jin-Heng Li. "Recent advances in photoelectrochemical cells (PECs) for organic synthesis." Organic Chemistry Frontiers 7, no. 14 (2020): 1895–902. http://dx.doi.org/10.1039/d0qo00486c.

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23

Ganiev, I. M., Q. K. Timergazin, N. N. Kabalnova, V. V. Shereshovets, and G. A. Tolstikov. "Reactions of Chlorine Dioxide with Organic Compounds." Eurasian Chemico-Technological Journal 7, no. 1 (September 21, 2016): 1. http://dx.doi.org/10.18321/ectj409.

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<p>Data on the reactivity of chlorine dioxide with organic compounds from various classes are summarized. Early investigations of the reactions of chlorine dioxide were occurred in aqueous or predominantly aqueous solutions in general, because it used in drinking water treatment and in industry as bleaching agent. However, chlorine dioxide was not used widely as reagent in organic synthesis. In last decades the number of publications on the studying interaction of the chlorine dioxide in organic medium increased. In table presented the rate constants reactions of chlorine dioxide with organic compounds published through 2004. Most of the rate constants were determined spectrophotometrically by decay kinetics of chlorine dioxide at 360 nm. Chlorine dioxide may be used for oxidation of organic compounds, because chlorine dioxide is enough reactive and selective as an oxidant with a wide range of organic compounds based on these reaction rate constants. But the application of chlorine dioxide as reagent in organic synthesis is restrained by the lack of data on the kinetics and mechanism of reactions involving chlorine dioxide, as well as data on the product yields and composition, temperature and solvent effects, and catalysts. The pathways of products formation and probable mechanisms of reactions are discussed in the review.</p>

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24

Anzovino, Mary E., and Stacey Lowery Bretz. "Organic chemistry students' ideas about nucleophiles and electrophiles: the role of charges and mechanisms." Chemistry Education Research and Practice 16, no. 4 (2015): 797–810. http://dx.doi.org/10.1039/c5rp00113g.

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Organic chemistry students struggle with reaction mechanisms and the electron-pushing formalism (EPF) used by practicing organic chemists. Faculty have identified an understanding of nucleophiles and electrophiles as one conceptual prerequisite to mastery of the EPF, but little is known about organic chemistry students' knowledge of nucleophiles and electrophiles. This research explored the ideas held by second-semester organic chemistry students about nucleophiles and electrophiles, finding that these students prioritize structure over function, relying primarily on charges to define and identify such species, both in general and in the context of specific chemical reactions. Contrary to faculty who view knowledge of nucleophiles and electrophiles as prerequisite to learning mechanisms and EPF, students demonstrated that they needed to know the mechanism of a reaction before they were able to assess whether the reaction involved nucleophiles and electrophiles or not.

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25

Croce, A. E. "First-order parallel and consecutive reaction mechanisms — Isosbestic points criterium." Canadian Journal of Chemistry 86, no. 9 (September 1, 2008): 918–24. http://dx.doi.org/10.1139/v08-098.

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A criterium for the selection of reaction mechanism derived from a condition for isosbestic points occurrence is presented. Analytical relationships involving the molar absorption coefficients of the species, which participate in a mechanism of parallel first-order reactions and the corresponding rate coefficients, are also reported. A model system of four species that present overlapping absorption spectra may correspond to the reactant and products of a system of parallel or consecutive first-order reactions. In the first case, under experimental conditions in which the absorbances are additive, the presence of an isosbestic point in the spectrum of the reaction mixture at a given wavelength leads to a time-independent ratio of the degree of advancement of reaction variables. From this, relevant kinetic information may be extracted, namely, the ratio of the reaction rate coefficients. Moreover, the occurrence of isosbestic points allows discarding the second mechanism. This conclusion is independent of the number of absorbing species. Model calculated examples show the application of the equations here derived. The resolution for the general case of mechanisms of N first-order reactions is provided.Key words: chemical kinetics, time-resolved absorption spectra, reaction mechanism.

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26

KOCOVSKY, P. "ChemInform Abstract: Addition Reactions: Polar Addition (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145331.

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27

Scholz, Sebastian, Denis Kondakov, Björn Lüssem, and Karl Leo. "Degradation Mechanisms and Reactions in Organic Light-Emitting Devices." Chemical Reviews 115, no. 16 (July 31, 2015): 8449–503. http://dx.doi.org/10.1021/cr400704v.

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28

Norcorss, Bruce E. "Advanced organic chemistry: reactions mechanisms, and structure (Mach, Jerry)." Journal of Chemical Education 65, no. 5 (May 1988): A139. http://dx.doi.org/10.1021/ed065pa139.2.

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29

Młochowski, Jacek, Monika Brząszcz, Mirosław Giurg, Jerzy Palus, and Halina Wójtowicz. "Selenium-Promoted Oxidation of Organic Compounds: Reactions and Mechanisms." European Journal of Organic Chemistry 2003, no. 22 (November 2003): 4329–39. http://dx.doi.org/10.1002/ejoc.200300230.

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30

KOCOVSKY, P. "ChemInform Abstract: Addition Reactions: Polar Addition (Organic Reaction Mechanisms)." ChemInform 25, no. 13 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199413289.

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31

HANSON, P. "ChemInform Abstract: Radical Reactions. Part 1. (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145321.

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32

NONHEBEL, D. C. "ChemInform Abstract: Radical Reactions. Part 2. (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145322.

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33

Alder, Roger W. "Advanced organic chemistry. reactions, mechanisms and structure. 3rd edition." Endeavour 9, no. 4 (January 1985): 206. http://dx.doi.org/10.1016/0160-9327(85)90091-2.

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34

Jenkin, Michael E., Richard Valorso, Bernard Aumont, Andrew R. Rickard, and Timothy J. Wallington. "Estimation of rate coefficients and branching ratios for gas-phase reactions of OH with aromatic organic compounds for use in automated mechanism construction." Atmospheric Chemistry and Physics 18, no. 13 (July 4, 2018): 9329–49. http://dx.doi.org/10.5194/acp-18-9329-2018.

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Abstract. Reaction with the hydroxyl (OH) radical is the dominant removal process for volatile organic compounds (VOCs) in the atmosphere. Rate coefficients for the reactions of OH with VOCs are therefore essential parameters for chemical mechanisms used in chemistry transport models, and are required more generally for impact assessments involving estimation of atmospheric lifetimes or oxidation rates for VOCs. A structure–activity relationship (SAR) method is presented for the reactions of OH with aromatic organic compounds, with the reactions of aliphatic organic compounds considered in the preceding companion paper. The SAR is optimized using a preferred set of data including reactions of OH with 67 monocyclic aromatic hydrocarbons and oxygenated organic compounds. In each case, the rate coefficient is defined in terms of a summation of partial rate coefficients for H abstraction or OH addition at each relevant site in the given organic compound, so that the attack distribution is defined. The SAR can therefore guide the representation of the OH reactions in the next generation of explicit detailed chemical mechanisms. Rules governing the representation of the reactions of the product radicals under tropospheric conditions are also summarized, specifically the rapid reaction sequences initiated by their reactions with O2.

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35

DiLorenzo, Melanie, Shantheni Ganesh, Lily Tadayon, Jinhua Chen, Mitchell R. M. Bruce, and Alice E. Bruce. "Reactions of Organic Disulfides and Gold(I) Complexes." Metal-Based Drugs 6, no. 4-5 (January 1, 1999): 247–53. http://dx.doi.org/10.1155/mbd.1999.247.

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Gold-thiolate/disulfide exchange reactions of (p-SC6H4Cl)2 with Ph3PAu(SC6H4CH3) , dppm(AuSC6H4CH3)2, and dppe(AuSC6H4CH3)2 were investigated. The rate of reactivity of the gold-thiolate complexes with (p-SC6H4Cl)2 is: dppm(AuSC6H4CH3)2>> dppe(AuSC6H4CH3)2>Ph3PAu(SC6H4CH3). This order correlates with conductivity measurements and two ionic mechanisms have been evaluated. H1 NMR experiments demonstrate that in the reaction of dppm(AuSC6H4CH3)2 with (p-SC6H4Cl)2, the mixed disulfide, ClC6H4SSC6H4CH3, forms first, followed by the formation of (p-SC6H4CH3)2. The rate law is first order in (pp-SC6H4Cl)2 and partial order in dppm(AuSC6H4CH3)2. Results from electrochemical and chemical reactivity studies suggest that free thiolate is not involved in the gold-thiolate/disulfide exchange reaction. A more likely source of ions is the dissociation of a proton from the methylene backbone of the dppm ligand which has been shown to exchange with D2O. The implications of this are discussed in terms of a possible mechanism for the gold-thiolate/disulfide exchange reaction.

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36

Parker, Vernon D. "Is the single transition-state model appropriate for the fundamental reactions of organic chemistry?" Pure and Applied Chemistry 77, no. 11 (January 1, 2005): 1823–33. http://dx.doi.org/10.1351/pac200577111823.

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In recent years, we have reported that a number of organic reactions generally believed to follow simple second-order kinetics actually follow a more complex mechanism. This mechanism, the reversible consecutive second-order mechanism, involves the reversible formation of a kinetically significant reactant complex intermediate followed by irreversible product formation. The mechanism is illustrated for the general reaction between reactant and excess reagent under pseudo-first-order conditions in eq. i where kf' is the pseudo-first-order rate constant equal to kf[Excess Reagent].Reactant + Excess reagent = Reactant complex = Products (i)The mechanisms are determined for the various systems, and the kinetics of the complex mechanisms are resolved by our "non-steady-state kinetic data analysis". The basis for the non-steady-state kinetic method will be presented along with examples. The problems encountered in attempting to identify intermediates formed in low concentration will be discussed.

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37

Kapral, Raymond, Styliani Consta, and Daniel Laria. "1996 Polanyi Award Lecture Proton reactions in clusters." Canadian Journal of Chemistry 75, no. 1 (January 1, 1997): 1–8. http://dx.doi.org/10.1139/v97-001.

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Reactions in mesoscopic, molecular clusters may proceed by mechanisms and with rates that differ from those in bulk solvents. Two examples of reactions in large, liquid-state, molecular clusters are described to illustrate the distinctive features of these reactions: acid dissociation and proton transfer in aprotic, polar solvents. Both of these reactions involve proton dynamics so methods for dealing with mixed quantum–classical systems must be utilized to investigate the reaction dynamics. Surface versus bulk solvation effects play an important role in determining the reaction mechanisms as do the strong cluster fluctuations. Mechanisms for proton transfer within clusters that have no bulk analogs will be described. Keywords: proton reactions, mesoscopic clusters.

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38

Gan, Wenhui, Yuexian Ge, Yu Zhong, and Xin Yang. "The reactions of chlorine dioxide with inorganic and organic compounds in water treatment: kinetics and mechanisms." Environmental Science: Water Research & Technology 6, no. 9 (2020): 2287–312. http://dx.doi.org/10.1039/d0ew00231c.

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39

Oelgemöller, Michael, and Norbert Hoffmann. "Studies in organic and physical photochemistry – an interdisciplinary approach." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7392–442. http://dx.doi.org/10.1039/c6ob00842a.

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Organic photochemistry when applied to synthesis strongly interacts in a very fruitful way with physical chemistry. A profound understanding of the photochemical reaction mechanisms is indispensable for optimization and application of these reactions.

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40

Vázquez, Saulo, Xose Otero, and Emilio Martinez-Nunez. "A Trajectory-Based Method to Explore Reaction Mechanisms." Molecules 23, no. 12 (November 30, 2018): 3156. http://dx.doi.org/10.3390/molecules23123156.

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The tsscds method, recently developed in our group, discovers chemical reaction mechanisms with minimal human intervention. It employs accelerated molecular dynamics, spectral graph theory, statistical rate theory and stochastic simulations to uncover chemical reaction paths and to solve the kinetics at the experimental conditions. In the present review, its application to solve mechanistic/kinetics problems in different research areas will be presented. Examples will be given of reactions involved in photodissociation dynamics, mass spectrometry, combustion chemistry and organometallic catalysis. Some planned improvements will also be described.

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41

Jenkin, Michael E., Richard Valorso, Bernard Aumont, Andrew R. Rickard, and Timothy J. Wallington. "Estimation of rate coefficients and branching ratios for gas-phase reactions of OH with aliphatic organic compounds for use in automated mechanism construction." Atmospheric Chemistry and Physics 18, no. 13 (July 4, 2018): 9297–328. http://dx.doi.org/10.5194/acp-18-9297-2018.

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Abstract. Reaction with the hydroxyl (OH) radical is the dominant removal process for volatile organic compounds (VOCs) in the atmosphere. Rate coefficients for reactions of OH with VOCs are therefore essential parameters for chemical mechanisms used in chemistry transport models, and are required more generally for impact assessments involving the estimation of atmospheric lifetimes or oxidation rates for VOCs. Updated and extended structure–activity relationship (SAR) methods are presented for the reactions of OH with aliphatic organic compounds, with the reactions of aromatic organic compounds considered in a companion paper. The methods are optimized using a preferred set of data including reactions of OH with 489 aliphatic hydrocarbons and oxygenated organic compounds. In each case, the rate coefficient is defined in terms of a summation of partial rate coefficients for H abstraction or OH addition at each relevant site in the given organic compound, so that the attack distribution is defined. The information can therefore guide the representation of the OH reactions in the next generation of explicit detailed chemical mechanisms. Rules governing the representation of the subsequent reactions of the product radicals under tropospheric conditions are also summarized, specifically their reactions with O2 and competing processes.

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42

Lin, Shu-kun, and Jerry March. "March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th Edition." Molecules 6, no. 12 (December 31, 2001): 1064–65. http://dx.doi.org/10.3390/61201064.

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43

Lund, H., K. Daasbjerg, T. Lund, D. Occhailini, S. U. Pedersen, Lauri Niinistö, Stenbjörn Styring, Cecilia Tommos, Kurt Warncke, and Bryan R. Wood. "On Radical Anions in Elucidation of Mechanisms of Organic Reactions." Acta Chemica Scandinavica 51 (1997): 135–44. http://dx.doi.org/10.3891/acta.chem.scand.51-0135.

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44

Hammerich, Ole. "Electrochemical Reactions and Mechanisms in Organic Chemistry, By James Grimshaw." Electrochimica Acta 48, no. 11 (May 2003): 1623–24. http://dx.doi.org/10.1016/s0013-4686(03)00086-0.

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45

Ji, Pengju, John H. Atherton, and Michael I. Page. "The kinetics and mechanisms of organic reactions in liquid ammonia." Faraday Discuss. 145 (2010): 15–25. http://dx.doi.org/10.1039/b912261n.

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46

Ciaccia, Maria, and Stefano Di Stefano. "ChemInform Abstract: Mechanisms of Imine Exchange Reactions in Organic Solvents." ChemInform 46, no. 11 (February 24, 2015): no. http://dx.doi.org/10.1002/chin.201511324.

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47

King, James F., Joe Y. L. Lam, and Gabriele Ferrazzi. "Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media." Journal of Organic Chemistry 58, no. 5 (February 1993): 1128–35. http://dx.doi.org/10.1021/jo00057a027.

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Tian, Wei Quan, and Yan Alexander Wang. "Mechanisms of Staudinger Reactions within Density Functional Theory." Journal of Organic Chemistry 69, no. 13 (June 2004): 4299–308. http://dx.doi.org/10.1021/jo049702n.

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Nguyen, Thi Thanh Thuy, Anne Boussonnière, Estelle Banaszak, Anne-Sophie Castanet, Kim Phi Phung Nguyen, and Jacques Mortier. "Chemoselective Deprotonative Lithiation of Azobenzenes: Reactions and Mechanisms." Journal of Organic Chemistry 79, no. 6 (March 10, 2014): 2775–80. http://dx.doi.org/10.1021/jo500230q.

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Chen, J., R. J. Griffin, A. Grini, and P. Tulet. "Modeling secondary organic aerosol formation through cloud processing of organic compounds." Atmospheric Chemistry and Physics 7, no. 20 (October 17, 2007): 5343–55. http://dx.doi.org/10.5194/acp-7-5343-2007.

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Abstract:

Abstract. Interest in the potential formation of secondary organic aerosol (SOA) through reactions of organic compounds in condensed aqueous phases is growing. In this study, the potential formation of SOA from irreversible aqueous-phase reactions of organic species in clouds was investigated. A new proposed aqueous-phase chemistry mechanism (AqChem) is coupled with the existing gas-phase Caltech Atmospheric Chemistry Mechanism (CACM) and the Model to Predict the Multiphase Partitioning of Organics (MPMPO) that simulate SOA formation. AqChem treats irreversible organic reactions that lead mainly to the formation of carboxylic acids, which are usually less volatile than the corresponding aldehydic compounds. Zero-dimensional model simulations were performed for tropospheric conditions with clouds present for three consecutive hours per day. Zero-dimensional model simulations show that 48-h average SOA formation is increased by 27% for a rural scenario with strong monoterpene emissions and 7% for an urban scenario with strong emissions of aromatic compounds, respectively, when irreversible organic reactions in clouds are considered. AqChem was also incorporated into the Community Multiscale Air Quality Model (CMAQ) version 4.4 with CACM/MPMPO and applied to a previously studied photochemical episode (3–4 August 2004) focusing on the eastern United States. The CMAQ study indicates that the maximum contribution of SOA formation from irreversible reactions of organics in clouds is 0.28 μg m−3 for 24-h average concentrations and 0.60 μg m−3 for one-hour average concentrations at certain locations. On average, domain-wide surface SOA predictions for the episode are increased by 9% when irreversible, in-cloud processing of organics is considered. Because aldehydes of carbon number greater than four are assumed to convert fully to the corresponding carboxylic acids upon reaction with OH in cloud droplets and this assumption may overestimate carboxylic acid formation from this reaction route, the present study provides an upper bound estimate of SOA formation via this pathway.

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