| Titre : | Estimation de logP de quelques dérivés ferrocèniques basée sur le concept de contributions des fragmentations du soluté |
| Auteurs : | Ridha Ahmedi, Auteur ; salah Belaidi, Directeur de thèse |
| Type de document : | Monographie imprimée |
| Editeur : | Biskra [Algerie] : Université Mohamed Kheider, 2013 |
| Format : | 235p / 30CM |
| Accompagnement : | CD |
| Langues: | Français |
| Mots-clés: | Coefficient de partage,logP,lipophilicité,dérivés de ferrocène,l'extraction liquide-liquide,hydrophilicité.,معامل التوزيعمحب للدهون,مشتقات الفيروسان، استخلاص سائل- سائل,محب للماء Partition coefficient,lipophilicity,ferrocene derivatives,liquid-liquid extraction,hydrophilicity. |
| Résumé : |
Le coefficient de partage dans le système octanol-eau, exprimée par P, est une propriété physico-chimique principale, basées sur la quelle plusieurs domaines scientifique telles que Pharmacologie et chimie agricole. Ce travail décrit une nouvelle et simple méthode pour déterminer des valeurs de LogP pour un grand nombre de dérivés de ferrocène en utilisant le calcul théorique et la prévision de la littérature. Les calculs sont basés sur l'adaptation de certaines méthodes existantes telles que Rekker, XLogP, AFC, et ALogP. Pour valider les méthodes de calcul proposées, logP d’un nombre des drivées ferrocéniques ont été mesurés en utilisant la voltammetrie à onde carrée. Toutes les valeurs de logP des dérivés de ferrocène obtenues par les différentes méthodes proposées sont très proches l'une de l'autre et en bon accord avec les valeurs expérimentales. Octanol–water partition coefficient, P, is a key physicochemical property for many filed of sciences such as pharmaceutical drugs, analytical chemistry, environmental science in the assessment of environmental fate, transport of organic chemicals and agrochemicals. This work describes new methods for determining logP values for a large number of ferrocene derivatives with widely varying structure, size and function using theoretical calculation and prediction from literature. Calculations are based on the adaptation of some existing methods such as Rekker, XLogP and ALogP. In order to validate our proposed theoretical method partition coefficients of a numerous ferrocene derivatives were also successfully determined, using for the first time square wave voltammetry techniques.Values of experimental and calculated logP of substituted ferrocene are in good agreement. في نظام أوكتانول – ماء ، من أهم الخصائص الفيزيو- كيميائية في العديد من العلوم ، P يعتبر معامل التوزيع للعديد LogP كالصيدلة, الكيمياء الزراعية, الكيمياء التحليلية و البيئة . يصف هذا العمل طرق نظرية جديدة لتحديد قيم و XLogP , Rekker من مشتقات الفيروسان والتنبؤ بها حسابيا . نعتمد في الحساب على تكييف الطرق النظرية لعدد من مشتقات الفيروسان مخبريا logP من أجل التاكد من نجاعة التنبؤ ات بالطرق النظرية قمنا بقياس ALogP لمشتقات الفيروسان المتحصل عليها حسابيا بمختلف هذه الطرق LogP باستعمال تقنية فولطامتري الموجة المربعة. قيم متقاربة في ما بينها ومتوافقة مع القيم التجريبية. |
| Sommaire : |
Abstract Table of contents List of tables List of figures List of abbreviations Summary CHAPTER I: Bibliographic overview I-1 - Octanol – water partition coefficient… I-2- Thermodynamics aspects of partition coefficient. I-2-1-The influence of thermodynamic factors on solute transfer. I-2-1-1-The influence of the transfer enthalpy ΔHw→oo. I-2-1-2-The influence of the transfer entropy ΔSw→oo. I-3- Partition coefficient history. I-4-Partition coefficient prediction methods… I-5-Partition coefficient determination methods. I-6-Chemical structure and properties of ferrocene… CHAPTER II: Octanol-water partition coefficients prediction and measurement methods II -1-Rekker method… II-1-1-Introduction… II-1-2-Principle of the Rekker approach. II-1-3-Development of Rekker method logP according to Rekker method. II-1-5- Interactions rules II-1-5-1-Saturated aliphatic hydrocarbon chains. II-1-5-2-Unsaturated aliphatic hydrocarbon chains. II-1-5-3-Saturated aliphatic hydrocarbon rings… II-1-5-4-Aromatic hydrocarbons ring. II-1-5-5-Fused rings in aromatic compounds II-1-5 -6- Jointed rings in aromatic compounds… II-1-5 -7- Basic fragment linked to aromatic ring. II-1-5-8- Basic fragment linking two aromatic rings or cross-conjugation. II-1-5-9-Conjugated bonds. II-1-5-10-Electronic effects between polar fragment or Proximity effects. II-1-5-11-Branching to a carbon bearing a polar fragment. II-1-5 -12- Hydrogen bonding. II-1-5-13-Hydrogen attached to electronegative fragments groups.. II-1-5-14-Decoupling of resonance. II-1-5-15-Resonance interaction. II-1-5-16-Oxygen connected to an aromatic ring via one carbon.method. II-2-1-Introduction. II-2-2-Principle of the XlogP method. II-2-3-Examples of calculation of logP according to XlogP method. II-2-4- Interactions rules… II-2-4-1-Hydrophobic carbon… II-2-4-2- Amino acid. II-2-4-3- Intramolecular hydrogen Bond. II-2-4-4- Halogen-Halogen 1-3 (Geminal) Interaction… II-3- AlogP method. II-3- 1-Introduction… II-3- 2- Principle of the AlogP approach… II-3- 3- Examples of calculation of logP according to AlogP method. II-4-logP measurement methods. II-4-1-Introduction. II-4-1-1- Shake flask method… II-4-1-2- Stir-flask method. II-4-1-3-Chromatography method… II-4-1-4- Potentiometric method… 51II-4-1-5- Voltammetric methods. II-4-2- Literature review II-4-2- 1- Electrochemical properties of ferrocene. II-4-2- 2-Electroanalytical chemistry. II-4-2-3- Voltammetric methods… II-4-2-4- Current in voltammetry… II-4-2-5- Square-wave voltammetry… II-4-2-6- Devloppement of square wave voltammetry CHAPTER III: Calculation and measurement of octanol- water partition coefficients of ferrocene derivatives III-1 -Rekker method for octanol-water partition coefficients determination. III-1-1- Introduction. III-1-2- Determination procedure. III-1-2-1- Adaptation of the Rekker approach. III-1-2-2- Specific correction factor rule for ferrocenyl ring III-1-2-2-1-Structural bonding of ferrocene. III-1-2-2-2- Correction rule for ferrocenyl ring connected to hydroxyl via carbons. III-1-3- Calculation and validation of our model. III-1-4- Discussion of results. III-1-5- Conclusion.. III-2-XlogP method for octanol-water partition coefficients determination. III-2-1-Introduction… III-2-2-Determination procedure… III-2-2-1- Adaptation of XlogP approach. III-2-2-2- Calculation and validation of the method… III-2-3-Discussion of results. III-2- 4- Conclusion. III-3- AlogP method for octanol-water partition coefficients determination. III-3-1- Introduction… III-3- 2- Determination procedure. III-3- 2-1-Adaptation of the AlogP approach… III- 3- 2-2- Calculation and validation of our model… III-3-3- Discussion of results… III-3- 4- Conclusion III-4-Square wave method for octanol-water partition coefficients determination. III-4-1- Material and instrumentation III-4-1-1-Material. III-4-1-2-Instrumentation and software… III-4-2- Measurement procedure. III-4-2-1- General procedure for square wave voltammetry. III-4-2-2- General procedure for the preparation of calibration curve III-4-2-3- General procedure for the preparation of real simple voltammogram…… III-4-2-4- Determination of partition coefficient of ferrocene derivatives. III-4-2-4-1- Determination of partition coefficient of ferrocene. III-4-2-4-2- Determination of partition coefficient of 1-ferrocenylethanol. III-4-2-4-3- Determination of partition coefficient of N-Ferrocenymethyl-N- phenylpropionamide. III-4-2-4-4- Determination of partition coefficient of N-Ferrocenymethyl-N- phenylacetamide III-4-2-4-5- Determination of partition coefficient of ferrocenyl-2- nitro phenyl. III-4-2-4-6-Determinationof partition coefficient of ferrocenyl-3- nitrophenyl III-4-2-4-7-Determination of partition coefficient of N-ferrocenylmethyl aniline. III-4-2-4-8-Determination of partition coefficient of N’-Ferrocenylmethyl-N’-phenylbenzohydrazide. III-4-2-4-9-Determination of partition coefficient of 2- (ferrocenylmethyl amino) benzonitrile. III-4-2-4-10-Determination of partition coefficient of 4- (ferrocenylmethyl amino) benzonitrile. III-4-3-Validation of electrochemical method… III-4-3-1- Determination of partition coefficient of ferrocene… III-4-3-2- Determination of partition coefficient of 1-ferrocenylethanol… III-4-4-Resultats and discussion… III-4- 5- Conclusion General conclusion References. |
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| Cote | Support | Localisation | Statut | Emplacement | |
|---|---|---|---|---|---|
| TH/0326 | Thèse de doctorat | BIB.FAC.ST. | Empruntable | Salle de mémoires et de théses |
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