Can Electric Field Modulate the Formaldehyde Hydration Reactivity?
Article Sidebar
Main Article Content
บทคัดย่อ
Previous studies have shown that formaldehyde hydration CH2O + H2O, producing methanediol CH2(OH)2, can be catalyzed by the active participation of water molecules at the water droplet surface. In such cases, water molecules form a hydrogen bonding network that effectively promotes the proton relay. Considering that electric fields can exist at water interfaces, we evaluated whether an electric field can affect the water catalyzed CH2O....(H2O)2→ CH2(OH)2...H2O reaction. Using B3LYP/6-311+G(2d,2p), we evaluated the effect of geometry relaxation when an electric field is applied to this reaction. When a negative electric field is applied along the carbonyl carbon and water oxygen atom, the activation energy decreases, and the reaction becomes more exothermic. Furthermore, the hydrogen bonding network of the CH2(OH)2...H2O complex was disrupted when the field was +0.153 volts/𝐴˚. Thus, we theoretically found that the electric field can have a profound effect on disrupting important hydrogen bonding networks and can affect the reactivity.
Article Details
อนุญาตภายใต้เงื่อนไข Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
เอกสารอ้างอิง
Franco B, Blumenstock T, Cho C, Clarisse L, Clerbaux C, Coheur PF, et al. Ubiquitous atmospheric production of organic acids mediated by cloud droplets. Nature. 2021;593(7858):233-7.
Chao W, Hsieh J-T, Chang C-H, Lin JJ-M. Direct kinetic measurement of the reaction of the simplest Criegee intermediate with water vapor. Science. 2015;347:751-4.
Chao W, Yin C, Takahashi K, Lin JJM. Hydrogen-Bonding Mediated Reactions of Criegee Intermediates in the Gas Phase: Competition between Bimolecular and Termolecular Reactions and the Catalytic Role of Water. J Phys Chem A. 2019;123(39):8336-48.
Kramer ZC, Takahashi K, Vaida V, Skodje RT. Will water act as a photocatalyst for cluster phase chemical reactions? Vibrational overtone-induced dehydration reaction of methanediol. J Chem Phys. 2012;136(16).
Burevschi E, Peña I, Sanz ME. Geminal Diol Formation from the Interaction of a Ketone with Water in the Gas Phase: Structure and Reactivity of Cyclooctanone-(H2O)1,2 Clusters. J
Phys Chem Lett. 2021;12(51):12419-25.
Inaba S. Theoretical Study of Decomposition of Methanediol in Aqueous Solution. J Phys Chem A. 2015:150514121000000.
Delcroix P, Pagliai M, Cardini G, Bégué D, Hanoune B. Structural and Spectroscopic Properties of Methanediol in Aqueous Solutions from Quantum Chemistry Calculations and Ab Initio Molecular Dynamics Simulations. J Phys Chem A. 2015;119(2):290-8.
Nguyen TL, Peeters J, Müller J-F, Perera A, Bross DH, Ruscic B, et al. Methanediol from cloud-processed formaldehyde is only a minor source of atmospheric formic acid. Proc Natl Acad Sci U S A. 2023;120(48):e2304650120.
Tarbuck TL, Ota ST, Richmond GL. Spectroscopic studies of solvated hydrogen and hydroxide ions at aqueous surfaces. J Am Chem Soc. 2006;128(45):14519-27.
Buch V, Milet A, Vácha R, Jungwirth P, Devlin JP. Water surface is acidic. Proc Natl Acad Sci U S A. 2007;104(18):7342-7.
Tian C, Ji N, Waychunas GA, Shen YR. Interfacial structures of acidic and basic aqueous solutions. J Am Chem Soc. 2008;130(39):13033-9.
Beattie JK, Djerdjev AM, Warr GG. The surface of neat water is basic. Faraday Discuss. 2009;141:31-9.
Mundy CJ, Kuo IFW, Tuckerman ME, Lee HS, Tobias DJ. Hydroxide anion at the air-water interface. Chem Phys Lett. 2009;481(1-3):2-8.
Hao H, Leven I, Head-Gordon T. Can electric fields drive chemistry for an aqueous microdroplet? Nat Commun. 2022;13(1):280.
Stuyver T, Ramanan R, Mallick D, Shaik S. Oriented (Local) Electric Fields Drive the Millionfold Enhancement of the HAbstraction Catalysis Observed for Synthetic Metalloenzyme Analogues. Angew Chem Int Ed Engl. 2020;59(20):7915-20.
Shaik S, Ramanan R, Danovich D, Mandal D. Structure and reactivity/selectivity control by oriented-external electric fields. Chem Soc Rev. 2018;47(14):5125-45.
Aragonès AC, Haworth NL, Darwish N, Ciampi S, Mannix EJ, Wallace GG, et al. Electrostatic catalysis of a Diels–Alder reaction. Nature. 2016;531(7592):88-91.
Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993;98(7):5648-52.
Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37(2):785-9.
Krishnan R, Binkley JS, Seeger R, Pople JA. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys. 1980;72(1):650-4.
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 16, Revision A.03. 2016.
Benco L, Tunega D, Hafner J, Lischka H. Upper Limit of the O−H∙∙∙O Hydrogen Bond. Ab Initio Study of the Kaolinite Structure. J Phys Chem B. 2001;105(44):10812-7.
