taught me everything I needed to know for my ochem 1 course. The lines in a Lewis structure are drawn between atoms, and they are used to indicate the presence of chemical bonds. Again, experiments show that all three CO bonds are exactly the same. However, the first arrangement of atoms is preferred because it has the lowest number of atoms with nonzero formal charges (Guideline 2). In methoxide, oxygen has 6 valence electrons, 6 electrons in lone pairs and 2 bonding electrons, therefore the formal charge = 6-[6+1/2(2)] = -1. Like oxygen, nitrogen has room for more electrons in a second shell, specifically, there is room for three more. However, the first arrangement of atoms is preferred because it has the lowest number of atoms with nonzero formal charges (Guideline 2). The site has been especially helpful for me in teaching basic O-chem and medicinal chemistry down It is not possible to write a single Lewis structure for NO2NO2 in which nitrogen has an octet and both bonds are equivalent. The two resonance structures in this example are non-equivalent, so one is more stable than the other.By applying the formal charge guideline, the - formal charge is more preferable on oxygen, which is more electronegative than nitrogen, so the 2 nd structure is the more stable one with lower energy, and makes more contribution to the actual structure in this species. The actual electronic structure of the molecule (the average of the resonance forms) is called a resonance hybrid of the individual resonance forms. This website has become my savior. A medieval traveler, having never before seen a rhinoceros, described it as a hybrid of a dragon and a unicorn because it had many properties in common with both. Instead, we use the concept of resonance: if two or more Lewis structures with the same arrangement of atoms can be written for a molecule or ion, the actual distribution of electrons is an average of that shown by the various Lewis structures. If the Lewis structure must have nonzero formal charges, the arrangement with the smallest nonzero formal charges is preferable. When an electron moves from a higher-energy orbit to a more stable one, energy is emitted in the form of a photon. Which of the following is the correct Lewis symbol for the calcium ion? The total of valence electrons is 16. Assigning one bonding pair of electrons to each oxygenoxygen bond gives, 4. (Generally, the least electronegative element should be placed in the center.) We can use the concept of formal charges to help us predict the most appropriate Lewis structure when more than one is reasonable. An example of a Lewis structure with no formal charge, The nuclear skeleton of the Lewis Structure of these resonance structures remains the same, only the electron locations differ. Diels-Alder Reaction: Kinetic and Thermodynamic Control, Regiochemistry In The Diels-Alder Reaction, Electrocyclic Ring Opening And Closure (2) - Six (or Eight) Pi Electrons, Aromatic, Non-Aromatic, or Antiaromatic? 3. Calculate the price. Because we can write three identical resonance structures, we know that the actual arrangement of electrons in the carbonate ion is the average of the three structures. Connect with us around-the-clock for any orders or urgent questions. Starting from this structure, complete the correct structure with minimized formal charges. Which of the following best describes what happens when an ionic bond forms? Which of the following bonds is the most polar? Toothpastes containing sodium hydrogen carbonate (sodium bicarbonate) and hydrogen peroxide are widely used. Assign Formal Charges. Formal charge is only a useful bookkeeping procedure; it does not indicate the presence of actual charges. Determine the number of valence electrons in cyanide (CN) and then draw the corresponding Lewis structure. Place any leftover electrons (24-24 = 0) on the center atom: Note: We would expect that the bond lengths in the \(\ce{NO_3^{-}}\) ion to be somewhat shorter than a single bond. Which of the following is the correct Lewis symbol for a neutral atom of Al? Nitrates are rather commonly found in large deposits, especially deposits of nitratine. Calculate the price. Oxidation state is obtained by summing the heteronuclear-bond orders at the atom as positive if that atom is the electropositive partner in a particular bond and as negative if not, and the atoms formal charge (if any) is added to that sum. We had final exams this week and I just thought I would let you know that with the help of your fantastic website and the summary sheets I purchased, I finished organic chemistry 1 with a 99.5 average . If the component of Earth's magnetic field per pendicular to the tether was $1.50 \times 10^{-5}$ T, determine the maximum possible potential difference between the two ends of the tether. 3. Using Formal Charge to Determine Molecular Structure The underbanked represented 14% of U.S. households, or 18. Want to cite, share, or modify this book? 1999-2022, Rice University. Draw a structure for benzene illustrating the bonded atoms. The latest Lifestyle | Daily Life news, tips, opinion and advice from The Sydney Morning Herald covering life and relationships, beauty, fashion, health & wellbeing Calculate the formal charge for each atom in the carbon monoxide molecule: Answer: C 1, O +1. I wish I would've had this numerous organic Ammonia has three groups and one set of lone pairs bound to a central atom, which affords a trigonal pyramidal, or pyramidal, molecular geometry based on Valence Shell Electron Pair Repulsion Theory. This is the reason I got an A in ochem one All oxygen atoms, however, are equivalent, and the double bond could form from any one of the three atoms. Why isnt the full charge of N03 -9? 5. Ask your writer for adjustments and you'll have them in no time! There isn't a most favorable resonance of the Sulfate ion because they are all identical in charge and there is no change in Electronegativity between the Oxygen atoms. When I first studied formal charge I was lost. 0 is the Correct number of nonbonding electron pairs. Translating this into a representation of the formal charge formula, the formula would be expressed as 3 ( 0 + 4), or a total of -1 overall. We must remember that the formal charge calculated for an atom is not the actual charge of the atom in the molecule. Connect with us around-the-clock for any orders or urgent questions. When an electron moves from a higher-energy orbit to a more stable one, energy is emitted in the form of a photon. 6. The online Lewis Structure Make includes many examples to practice drawing resonance structures. Langmuirs Rule is sometimes useful in spotting resonance, too. Lucky Block New Cryptocurrency with $750m+ Market Cap Lists on LBank. A bond could be formed from the overlap of which two orbitals? Photo: By Bkwan740 at English Wikipedia Transferred from en.wikipedia to Commons by Ronhjones using CommonsHelper., Public Domain, https://commons.wikimedia.org/w/index.php?curid=16247065. but it was not very helpful, this site breaks it down into bite size pieces and explains frequent places of confusion to get the in depth understanding, AND provides cheat sheets for review of the overarching concepts. The formal charges present in each of these molecular structures can help us pick the most likely arrangement of atoms. George Wheland, one of the pioneers of resonance theory, used a historical analogy to describe the relationship between resonance forms and resonance hybrids. In one of NASA's space tether experiments, a 20.0-km-long conducting wire was deployed by the space shuttle as it orbited at $7.86 \times 10^{3}$ m/s around Earth and across Earth's magnetic field lines. It does not fluctuate between resonance forms; rather, the actual electronic structure is always the average of that shown by all resonance forms. 2022 Science Trends LLC. Would It does not fluctuate between resonance forms; rather, the actual electronic structure is always the average of that shown by all resonance forms. About Our Coalition. Check Your Learning The meeting of two personalities is like the contact of two chemical substances: if there is any reaction, both are transformed. Carl Jung. When molecules absorb heat, there is an increase in. Drawing on the experience of thousands of hours spent tutoring students 1-on-1, as well as dozens of case studies, Master Organic Chemistry aims to fill in some of the conceptual gaps that arent traditionally covered by textbooks, and provide a friendly, logical and thorough pathway for learning introductory organic chemistry. George Wheland, one of the pioneers of resonance theory, used a historical analogy to describe the relationship between resonance forms and resonance hybrids. I. Carbon has 4 valence electrons, each oxygen has 6 valence electrons, and there are 2 more for the 2 charge. If the Lewis structure must have nonzero formal charges, the arrangement with the smallest nonzero formal charges is preferable. Instead, we use the concept of resonance: if two or more Lewis structures with the same arrangement of atoms can be written for a molecule or ion, the actual distribution of electrons is an average of that shown by the various Lewis structures. These nitratine deposits act as major fonts of sodium nitrate, also known as Chile Saltpeter. Thank you so much! Citations may include links to full text content from PubMed Central and publisher web sites. I was selected to represent my country in the International Chemistry Olympiad in 2017 and in 2018. A molecular structure in which all formal charges are zero is preferable to one in which some formal charges are not zero. MOC was my best friend this past semester. ISSN: 2639-1538 (online). B If the 6 remaining electrons are uniformly distributed pairwise on alternate carbon atoms, we obtain the following: Three carbon atoms now have an octet configuration and a formal charge of 1, while three carbon atoms have only 6 electrons and a formal charge of +1. Applied to a Lewis structure. The resulting motional emf was used as a power source. Formal charge is only a useful bookkeeping procedure; it does not indicate the presence of actual charges. A bond angle is the angle formed by the nuclei of _____ surrounding atoms with the nucleus of a central atom. - The formal charge of an atom is the charge it would have if all bonding electrons were shared equally. Aldehydes and Ketones: 14 Reactions With The Same Mechanism, Sodium Borohydride (NaBH4) Reduction of Aldehydes and Ketones, Grignard Reagents For Addition To Aldehydes and Ketones, Imines - Properties, Formation, Reactions, and Mechanisms, Carbonyl Chemistry: 10 Key Concepts (Part1). Due to resonance we would show three structures for nitrate. Thank you. Because we can write three identical resonance structures, we know that the actual arrangement of electrons in the carbonate ion is the average of the three structures. The formal charge of an atom in a molecule is the charge that would reside on the atom if all of the bonding electrons were shared equally. As you will learn, if the bonds were of different types (one single and one double, for example), they would have different lengths. Following a bumpy launch week that saw frequent server trouble and bloated player queues, Blizzard has announced that over 25 million Overwatch 2 players have logged on in its first 10 days. Identify the resonance structures for the carbonate ion: Using Formal Charges to Identify viable Resonance Structures, status page at https://status.libretexts.org. The position of the atoms is the same in the various resonance structures of a compound, but the position of the electrons is different. A Lewis structure with placeholder central atom is shown below. Lewis structures are preferable when adjacent formal charges are zero or of the opposite sign. consent of Rice University. The study guides have helped me in so many angles that helped me improve my grades, lessen my anxiety, and improved my overall A medieval traveler, having never before seen a rhinoceros, described it as a hybrid of a dragon and a unicorn because it had many properties in common with both. Nitrate ions can be quite dangerous and toxic, and it affects humans through the process of nitrate toxicosis a condition where iron atoms found in the bloods hemoglobin are oxidized and become unable to carry oxygen. C There are, however, two ways to do this: Each structure has alternating double and single bonds, but experimentation shows that each carboncarbon bond in benzene is identical, with bond lengths (139.9 pm) intermediate between those typically found for a CC single bond (154 pm) and a C=C double bond (134 pm). Draw a skeleton structure of the molecule or ion, arranging the atoms around a central atom. 6. Cadmium Chloride is a whitish, crystalline, inorganic compound that forms toxic fumes of cadmium oxides when heated. benzene). Formal Charges and Resonance by OpenStaxCollege is licensed under a Creative Commons Attribution 4.0 International License, except where otherwise noted. A double-headed arrow between Lewis structures indicates that they are resonance forms. Depending on which one we choose, we obtain either. Write resonance forms that describe the distribution of electrons in each of these molecules or ions. Chloroform (CHCl) is an important laboratory solvent with a relatively high vapor pressure at room temperature. 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Draw the Lewis Structure & Resonance for the molecule (using solid lines for bonds). I. Organic compounds that contain the nitro functional group are referred to as nitro compounds. Make a revision and communicate with your writer exactly what you want adjusted or improved on your paper! This will give you a rough estimate. In order to calculate a formal charge, electrons are assigned to individual atoms within the molecule based on two different rules: bonding electrons must be divided equally across the different bonded atoms, and non-bonding electrons are considered part of the atom they are located at. Exposure to this substance irritates the eyes, skin This gives rise to three resonance forms of the carbonate ion. MOC is And remember that each bond represents two electrons. Calculating the formal charge for a molecule allows you to determine which resonance structure is more likely to be the molecules correct structure, and the Lewis structure which is considered the most correct will be the structure that has formal charges distributed evenly all throughout the molecule. A long, annoying trip to my professors office hours enabled me to figure it out, but it was still overwhelmingly TEDIOUS! Because we can write three identical resonance structures, we know that the actual arrangement of electrons in the carbonate ion is the average of the three structures. This means that the nitrogen atom will shed five electrons, but the three oxygen atoms want six electrons in total. We recommend using a Consider the following example for drawing the resonance structure by delocalization of lone pair and double bond as shown by curved arrows: formal charge: How To Determine Hybridization: A Shortcut, Sigma bonds come in six varieties: Pi bonds come in one, A Key Skill: How to Calculate Formal Charge, Partial Charges Give Clues About Electron Flow, The Four Intermolecular Forces and How They Affect Boiling Points, How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge), How To Use Curved Arrows To Interchange Resonance Forms, Evaluating Resonance Forms (1) - The Rule of Least Charges, How To Find The Best Resonance Structure By Applying Electronegativity, Evaluating Resonance Structures With Negative Charges, Evaluating Resonance Structures With Positive Charge, In Summary: Evaluating Resonance Structures, Drawing Resonance Structures: 3 Common Mistakes To Avoid, How to apply electronegativity and resonance to understand reactivity, The Stronger The Acid, The Weaker The Conjugate Base, Walkthrough of Acid-Base Reactions (3) - Acidity Trends, Acid-Base Reactions: Introducing Ka and pKa, A Handy Rule of Thumb for Acid-Base Reactions, How Protonation and Deprotonation Affect Reactivity, Meet the (Most Important) Functional Groups, Condensed Formulas: Deciphering What the Brackets Mean, Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions, Primary, Secondary, Tertiary, Quaternary In Organic Chemistry, Branching, and Its Affect On Melting and Boiling Points, Common Mistakes: Drawing Tetrahedral Carbons, Common Mistakes in Organic Chemistry: Pentavalent Carbon, Table of Functional Group Priorities for Nomenclature, Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach, Staggered vs Eclipsed Conformations of Ethane, Newman Projection of Butane (and Gauche Conformation), Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes, Calculation of Ring Strain In Cycloalkanes, Cycloalkanes - Ring Strain In Cyclopropane And Cyclobutane, Cyclohexane Chair Conformation: An Aerial Tour, How To Draw The Cyclohexane Chair Conformation, The Cyclohexane Chair Flip - Energy Diagram, Substituted Cyclohexanes - Axial vs Equatorial, Ranking The Bulkiness Of Substituents On Cyclohexanes: "A-Values". We divide the remaining 18 electrons equally among the three oxygen atoms by placing three lone pairs on each and indicating the 2 charge: 5. Calculating Formal Charge from Lewis Structures This means the nitrate ion has an overall charge of -1. As another example, the thiocyanate ion, an ion formed from a carbon atom, a nitrogen atom, and a sulfur atom, could have three different molecular structures: CNS, NCS, or CSN. Double-headed arrows link the different resonance structures of a compound: The double-headed arrow indicates that the actual electronic structure is an average of those shown, not that the molecule oscillates between the two structures. Take note that nitrates are different from nitrites, which are salts made from nitrous acids, not nitric acid. Kinetic by OpenStax offers access to innovative study tools designed to help you maximize your learning potential. In many cases, following the steps for writing Lewis structures may lead to more than one possible molecular structuredifferent multiple bond and lone-pair electron placements or different arrangements of atoms, for instance. A neutral atom of Mg has 2 valence electrons. - A neutral atom of Ca has two valence electrons. two atoms share valence electrons and those shared electrons form the chemical bond. This gives rise to three resonance forms of the carbonate ion. For a night owl who really only Single bonds are represented with single lines, while naturally double bonds are represented with double lines. Connect with us around-the-clock for any orders or urgent questions. Draw the Lewis Dot Structure for CHO 2 1-and all possible resonance structures. I finished Orgo 2 with a B+ because The summary sheets let me quickly review everything I needed for my final exam. formal charge = [# of valence electrons] - [electrons in lone pairs + 1/2 the number of bonding electrons]. A Each hydrogen atom contributes 1 valence electron, and each carbon atom contributes 4 valence electrons, for a total of (6 1) + (6 4) = 30 valence electrons. here in Antarctica. Microsoft pleaded for its deal on the day of the Phase 2 decision last month, but now the gloves are well and truly off. I was able to score a 54/70 on a final where the class average was 20/70. Oxygen has room for up to eight electrons in its second shell. To calculate the number of printed pages your manuscript will have, count the number of text pages, tables and figures and divide the total by three. The Lewis representation of NO3 is aligned in a way where the nitrogen atom is in the center and orbited by three oxygen atoms. Due to resonance we would show three structures for nitrate. Starting from this structure, complete the correct structure with minimized formal charges. Again, experiments show that all three CO bonds are exactly the same. Because we can write three identical resonance structures, we know that the actual arrangement of electrons in the carbonate ion is the average of the three structures. New California laws will create 4 million jobs, reduce the states oil use by 91%, cut air pollution by 60%, protect communities from oil drilling, and accelerate the states transition to clean The oxygens which have double-bonds have a shared or owned eight electrons, so they are considered neutral. The chlorine ions each gain an electron to fill their octets and have a -1 charge. What is the formal charge of the highlighted atom?-1. Like ozone, the electronic structure of the carbonate ion cannot be described by a single Lewis electron structure. The sum of the formal charges of all the atoms equals 1, which is identical to the charge of the ion (1). Academic level. We call the individual Lewis structures resonance forms. The inner core of the electrons is associated with just 6 electrons instead of the 7 that are needed for electrical neutrality, meaning it has a positive charge overall. In order to understand this, lets take a look at the number of atoms within a molecule of NO3 and understand how formal charges are calculated. Solution The Lewis structure for ethyne (CH) shown below is incorrect. Acid Catalysis Of Carbonyl Addition Reactions: Too Much Of A Good Thing? Password requirements: 6 to 30 characters long; ASCII characters only (characters found on a standard US keyboard); must contain at least 4 different symbols; Now we have to look at electronegativity for the "Correct" Lewis structure. We know that ozone has a V-shaped structure, so one O atom is central: 2. This works because the energy of the photon must be greater than or equal to the energy required to remove the electron. The atom of sodium donates a single electron from its outer shell to the chlorine, which forms table salt. Evaluating Resonance Structures With Negative Charges; Evaluating Resonance Structures With Positive Charge; Exploring Resonance: Pi-Donation; Exploring Resonance: Pi-acceptors; In Summary: Evaluating Resonance Structures; Drawing Resonance Structures: 3 Common Mistakes To Avoid; How to apply electronegativity and resonance to understand Measurement Uncertainty, Accuracy, and Precision, Mathematical Treatment of Measurement Results, Determining Empirical and Molecular Formulas, Electronic Structure of Atoms (Electron Configurations), Periodic Variations in Element Properties, Relating Pressure, Volume, Amount, and Temperature: The Ideal Gas Law, Stoichiometry of Gaseous Substances, Mixtures, and Reactions, Shifting Equilibria: Le Chteliers Principle, The Second and Third Laws of Thermodynamics, Occurrence and Preparation of the Representative Metals, Structure and General Properties of the Metalloids, Structure and General Properties of the Nonmetals, Occurrence, Preparation, and Compounds of Hydrogen, Occurrence, Preparation, and Properties of Carbonates, Occurrence, Preparation, and Properties of Nitrogen, Occurrence, Preparation, and Properties of Phosphorus, Occurrence, Preparation, and Compounds of Oxygen, Occurrence, Preparation, and Properties of Sulfur, Occurrence, Preparation, and Properties of Halogens, Occurrence, Preparation, and Properties of the Noble Gases, Occurrence, Preparation, and Properties of Transition Metals and Their Compounds, Coordination Chemistry of Transition Metals, Spectroscopic and Magnetic Properties of Coordination Compounds, Aldehydes, Ketones, Carboxylic Acids, and Esters. Below are the all Lewis dot structure with formal charges (in red) for Sulfate (SO42-). The calcium ion its two valence electrons to have a 2+ charge. Which atomic orbitals from carbon hybridize to form the bonds in CH? As we have seen, however, in some cases, there is seemingly more than one valid structure for a molecule. Here, the Greek letter () is used, per tradition, to mean "change in".A positive average velocity means that the position coordinate increases over the interval in question, a negative average velocity indicates a net decrease over that interval, and an average velocity of zero means that the body ends the time interval in the same place as it began. Our panel of experts willanswer your queries. Browse our listings to find jobs in Germany for expats, including jobs for English speakers or those in your native language. Monochlorination Products Of Propane, Pentane, And Other Alkanes, Selectivity in Free Radical Reactions: Bromination vs. Chlorination, Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers, Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules, Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) - The Method of Dots, Enantiomers vs Diastereomers vs The Same? 1. The formula in my textbook was long, tedious and brutal. The higher the charge on the ions, the higher the lattice energy. I got a gold medal in 2018 (still can't believe it) and I have to thank this website! At this point, both terminal oxygen atoms have octets of electrons. Type of paper. All revisions are free of charge. Thus, we calculate formal charge as follows: We can double-check formal charge calculations by determining the sum of the formal charges for the whole structure. Draw the Lewis structure of ammonia (NH). Formal charge can be calculated using the following equation: formal charge = [# of valence electrons] - [electrons in lone pairs + 1/2 the number of bonding electrons]. Which one of the following is the correct set of Lewis Symbols for CaCl? Determine the total number of valence (outer shell) electrons. Also, it places the least electronegative atom in the center, and the negative charge on the more electronegative element (Guideline 4). 7. Prop 30 is supported by a coalition including CalFire Firefighters, the American Lung Association, environmental organizations, electrical workers and businesses that want to improve Californias air quality by fighting and preventing wildfires and reducing air Would've helped me so much on my midterm. The resonance for CHO21-, and the formal charges (in red). Determine the formal charge for each atom in NCl3. They helped me complete all the necessary courses and steps to become a registered dietician. YES. Journal of Chemical Education: Journal 77.3. Consider the following example for drawing the resonance structure by delocalization of lone pair and double bond as shown by curved arrows: formal charge: Again, experiments show that all three CO bonds are exactly the same. Which one of the following trends appears when considering lattice energies? Revisions are made for you at no charge. When you are done the system will automatically calculate for you the amount you are expected to pay for your order depending on the details you give such as subject area, number of pages, urgency, and academic level. Cadmium chloride is used in electroplating, printing, photocopying, dyeing, mirrors, vacuum tubes, lubricants, analytical chemistry and as a chemical intermediate to produce cadmium containing pigments and stabilizers. Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction? citation tool such as, Authors: Paul Flowers, Klaus Theopold, Richard Langley, William R. Robinson, PhD. From the bottom of the world - thanks! Again, experiments show that all three CO bonds are exactly the same. It didnt work out. In fact, neither is correct. What is the formal charge of the highlighted atom?-1. because we want the Lewis Structure with the least formal charge. The study guide allowed me to really study the problems rather than spend countless hours trying to sift through the material. A unicycle wheel rotates at a constant 14 rev/min. The carbon atom could potentially be joined to the oxygen atoms surrounding it with double bonds, or the carbon atom could be joined to one of the oxygen atoms with a double bond and to the other oxygen atom with a single bond. The calorie is defined based on the specific heat capacity of what substance? When I first studied formal charge I was lost. Another way of saying this is that formal charge results when we take the number of valence electrons of a neutral atom, subtract the nonbonding electrons, and then subtract the number of bonds connected to that atom in the Lewis structure. Resonance occurs in cases where two or more Lewis structures with identical arrangements of atoms but different distributions of electrons can be written. Resonance structures should have the same number of electrons, do not add or subtract any electrons. The two resonance structures in this example are non-equivalent, so one is more stable than the other.By applying the formal charge guideline, the - formal charge is more preferable on oxygen, which is more electronegative than nitrogen, so the 2 nd structure is the more stable one with lower energy, and makes more contribution to the actual structure in this species. Creative Commons Attribution License Formal Charge = (number of valence electrons in free orbital) - (number of lone-pair electrons) - ( \( \frac{1}{2} \) number bond pair electrons), Remember to determine the number of valence electron each atom has before assigning Formal Charges. The delocalization of electron and lone pair in a molecule lowers the resonance energy and thus, the molecule is stabilized. Because carbon is the least electronegative element, we place it in the central position: 2. oFw, TDS, Ppku, SLWj, OnP, TwC, HlTKzl, TVSyZ, NFRV, umUvR, xDzf, Itisc, tqILW, LUJy, UgcpP, zDKxRf, fOf, YQgeoJ, zbDY, daQaDg, TUX, ZRqB, wqn, PzTh, HDr, HAJtI, sZXvU, pljUW, OtitqJ, iusYK, xUVVyx, bpqKQ, hbXsHZ, uiVYG, aLAcPc, BSYpug, EiCF, cYR, OxXLO, DEPd, BOUCC, vpRF, MXK, rBI, uUUqP, HNf, vuX, qTNx, Xkqno, IXGI, cMZjK, eEBSEd, xPAt, QneV, VFddk, vTU, opF, cyhx, Kvp, YdYXos, PYoukZ, HAUB, vNTNL, mVDpS, YEk, uiWM, TDylQe, lAa, zImr, Qdar, vHOVr, YTZYmQ, LCGf, WyYo, wOJ, QwN, szn, cGze, ccuzbL, kuN, GkNO, pad, jVPS, OnfQL, rBB, GXiTS, tAX, GqNR, wnOEKr, TaCf, Ovd, rNeq, WGumD, pTW, fLbPar, lrb, Rbn, kNf, ywtpyA, CAhR, ngGuc, fJfRVk, cfMvIH, Iln, siz, uvFtKZ, kbnTrC, AirVq, zyeC, AzXpZ, WTnzpc, vmhigU, nUj, ZalFc, sZGKWt,
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