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Ab-Initio Calculation of the Rates of the Reactions Between Volatile Organic Compounds in Wine and Cations for Mass Spectrometry

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Ab-Initio Calculation of the Rates of the Reactions Between Volatile Organic Compounds in Wine and Cations for Mass Spectrometry Scuola di Dottorato in Fisica, Astrofisica e Fisica Applicata Dipartimento di Fisica Corso di Dottorato in Fisica, Astrofisica e Fisica Applicata Ciclo XXXIII Ab-initio Calculation of the Rates of the Reactions between Volatile Organic Compounds in Wine and Cations for Mass Spectrometry Settore Scientifico Disciplinare FIS/03 Supervisore: Prof. Nicola Manini Co-supervisore: Dr. Franco Biasioli Co-supervisore: Prof. Paolo Piseri Coordinatore: Prof. Matteo Paris Tesi di Dottorato di: Manjeet Kumar Anno Accademico 2019-2020 External Referees: Jonathan Beauchamp Giorgio Benedek Commission of the final examination: External Members: Saskia Van Ruth Luca Cappellin Internal Member: Nicola Manini Final examination: Date 18-12-2020 Università degli Studi di Milano, Dipartimento di Fisica, Milano, Italy Dedicated to my parents Cover illustration: Volatile Organic Compounds responsible for producing cork-taint in a bottle of wine. MIUR subjects: FIS/03, FIS/07, CHIM/01, CHIM/10 PACS: 82.20.Pm, 33.15.Ms, 31.15.Ar Abstract Wine is a complex mixture housing many aroma and flavor compounds giving it a unique texture and bouquet. These volatile organic compounds (VOCs), if present near the sensory threshold limits, may contribute positively to wine quality; however, excessive amounts can detract from quality, and are considered as a fault in wine. It is believed that nearly 10% of the world’s wine is affected from various types of faults. The most common and potent wine taint is 2,4,6-trichloroanisole (2,4,6-TCA), com- monly known as cork-taint molecule resulting from the cork stopper of wine bottles. 2,4,6- TCA produces intense ’musty’, ’mouldy’ ’earthy’ smelling in wine. Similar off-flavor smells are associated to compounds including geosmin and 2-methoxy- 3,5-dimethylpyrazine. We studied 74 such VOCs frequently present in wine. Determining concentration of VOCs in wine requires detection techniques to be fast, in real time, and with a detection limit as low as few parts per trillion by volume. The most frequently used techniques based on direct injection mass spectrometry, namely proton transfer reaction mass spectrometry (PTR-MS) and selected ion flow tube mass spectrometry (SIFT-MS), are being successfully employed in the measurements of VOCs concentrations. Quantification using these techniques usually relies on compound-by-compound instru- ment calibration. The calibration procedures are generally laborious and time consuming. The theoretical evaluation of the rate coefficients of ion-molecule reactions occurring in PTR-MS/SIFT-MS flow (drift) tubes is a practical alternative to calibration. In this thesis, we compute and report the rate coefficients for ion-molecule reactions, relevant for different experimental conditions, such as varied temperature and electric fields inside the drift tube. We have used well-established models based on capture cross-section collision and classical trajectories. These models rely on physical properties such as elec- tric dipole moment and polarizability of the volatile molecules. To compute these quantities we resorted to ab initio density functional theory. v Introduction The flavor of food products determines their sensory qualities, whilst their appearance and color provide the first indicators of quality. Flavor and texture in food products are critical in confirming or undermining the initial impression of our perception of the food. Wine is a popular food drink and has evolved as an integral part in our life, culture and diet since time immemorial. Over the years, the role of wine has evolved from cultural symbol to an important source of nutrition [1]. Two major components of wine are water and ethanol. The alcoholic content of wine is considered crucial to the stability, aging, and sensory properties of wine and produce multiple effects on taste and mouthfeel [2]. The alcohol in wine, mainly ethanol, produced during fermentation process, contributes to the formation of several volatile aromatic compounds (VOCs) including acetaldehyde, diacetyl, acetic acid and numerous other volatile compounds in wine. Apart from water and alcohol, many compounds typically present at trace level (< 10 g/L) are responsible for most of the flavor and color of wine and many key odorants are found at part-per-trillion (ng/L) concentrations. It is worth mentioning that VOCs appear in wine are not unique to the wine but appear in coffee, beer, bread, spices, vegetables, cheese, and other foodstuffs. The VOCs in food and alcoholic beverages provide a flavor fingerprint that help us in recognizing hygienic foods and avoid poor or dangerous food choices. Wine flavor is characterized by the fine balance between number of different organic compounds. Above threshold concentration they deteriorate the quality of the wine and causing economic losses to the wineries and damage their reputation. A report published in 1983 by Nykänen and Suomalainen have reported around 1300 volatile compounds in wine and other alcoholic beverages [3]. Re- cent developments in various mass spectrometry techniques were able to detect tens of thousands chemical compounds in wine and the count might be even higher [4]. The VOCs play important role as they determine the flavor of grapes and wine made from it. Wine off-flavor and taint molecules produced can be classified by the follow- ing three stages of wine production: from grapes, during fermentation and while storage. The compounds present in grapes remain unchanged in the wine. Many new compounds form during alcoholic fermentation due to normal metabolism of sugars and amino acids. Other major sources such as improper storage and handling of wine, extraction from oak vii and abiotic transformation of precursor compounds can also produce microbial spoilage or chemical tainting in wine. The most problematic and highly potent molecule present in wine is 2,4,6-trichloroanisole. It results from cork stopper of wine bottles, usually called cork-taint, produces intense ’musty’, ’mouldy’, and ’earthy’ smells in the wine. Many terpenes such as 1,8-cineole and rotundone are responsible for ’spicy’ and ’mint’ like char- acter to the wine. 4-ethylcatechol is another major spoilage compound associated with Dekkera/Brettanomyces yeast resembles ’horsey’ aroma. Variety of sulfur compounds including dimethyl sulfide and disulfides produce smell like ’cooked cabbage’, ’cooked corn’, ‘cooked tomato’ or ‘molasses’ in many wines [5,6]. Therefore, accurate measurement of such trace level VOCs demand appropriate ana- lytic methods that are capable of separating and quantifying VOCs in a complex gas mix- ture, able to track concentrations that change rapidly over time and with high sensitivity and low detection range (pptv) [7]. The most frequently used techniques based on the direct injection mass spectrometry such as proton transfer reaction mass spectrometry (PTR-MS) and selected ion flow tube mass spectrometry (SIFT-MS) have been very successful in mea- suring VOCs concentrations. PTR-MS allows real-time monitoring of many VOCs with very low detection limit (pptv range) and with high sensitivity. SIFT-MS is characterized by its capability of switching between reagent ions, less than 10 ms, offers a substantial benefit in increased selectivity for the analysis of mixtures containing multiple analytes. + + + + The reagent ions such as H3O , NH4 , NO and O2 in SIFT-MS offer flexibility in the measurement of isobars and isomers [8]. It is worth noting that the same ion-molecule chemistry can be applied for PTR-MS/SIFT-MS measurements at thermal energy condi- tions. However at higher temperature, the PTR-MS working conditions are quite different due to the applied electric field. The applied electric field makes ion-molecule collisions far more energetic than thermal conditions. We have studied proton transfer and charge transfer reactions under collision based models and calculated rate coefficients of IMRs. The rate coefficients are vital in the quantification of VOCs in PTR-MS/SIFT-MS measure- ments as the rate coefficients omit the calibration requirement, since calibration procedures are generally laborious, time consuming and source of errors [9]. The IMRs are among the fastest chemical reactions and proceed without the activation energy [10]. The rate coefficients of such IMRs can be obtained from capture collision cross-section generally called collision rate coefficients. The magnitude of collision rate coefficients is obtained by physical properties such as dipole moment and polarizability of the reactants as suggested in average dipole orientation theory [11]. The basic long- range interactions between ion and polarizable neutral molecule involved are ion-induced and ion-permanent dipole interactions. Alternatively, ion-molecule rate coefficients can be obtained from classical trajectory calculations [12, 13]. We studied ion-molecule collisions through proton transfer and charge transfer reactions frequently occur in PTR-MS and SIFT-MS instruments. Also, we obtained physical and chemical parameters that influence viii the ion-molecule chemistry occurring in the PTR-MS and SIFT-MS flow (drift) tubes. Structure of the thesis is organized as follows: Chapters under part (I) present intro- duction and technical information about wine, wine analytic methods, chemistry of IMRs and theoretical procedures. Chapter (1) provides detailed review of wine and wine com- ponents present before and during the course of production. Various flavourant and aroma compounds responsible for wine flavor have been listed. Other than this, off-flavor and wine
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