Browse our listings to find jobs in Germany for expats, including jobs for English speakers or those in your native language. All revisions are free of charge. formal charge = [# of valence electrons] - [electrons in lone pairs + 1/2 the number of bonding electrons]. probably not have made an A last semester without it (I made exactly 90). Calculate the price. 3. Learning New Reactions: How Do The Electrons Move? To move an electron from a stable orbit to a more excited one, a photon of energy must be absorbed. In cases where nitrates are combined with other molecules, like when sodium combines with nitrate to form sodium nitrate or NaNo3, the single electron found in sodiums outer shell will be transferred over to N03, which makes it a nitrate ion and ends up making it have a -1 charge. Example 4.9. The higher the charge on the ions, the higher the lattice energy. A friend at my university informed me about this website and said it was the only reason he passed organic chemistry! Our mission is to improve educational access and learning for everyone. Langmuirs Rule is sometimes useful in spotting resonance, too. We can convert each lone pair to a bonding electron pair, which gives each atom an octet of electrons and a formal charge of 0, by making three C=C double bonds. We know that ozone has a V-shaped structure, so one O atom is central: 2. MOC was my best friend this past semester. Resonance is a way of describing delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by a single Lewis formula. 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. The meeting of two personalities is like the contact of two chemical substances: if there is any reaction, both are transformed. Carl Jung. This gives rise to three resonance forms of the carbonate ion. Hint: In this case, it is more stable (preferred) to place a negative charge on the larger atom. (SO) with minimized formal charges. Using Formal Charge to Determine Molecular Structure Connect with customer support around-the-clock for any orders or urgent questions. Calculate the formal charge for each atom in the carbon monoxide molecule: Answer: C 1, O +1. Determining formal charge yields the following: The structure with a terminal oxygen atom best satisfies the criteria for the most stable distribution of formal charge: The number of atoms with formal charges are minimized (Guideline 2), and there is no formal charge larger than one (Guideline 2). Ask your writer for adjustments and you'll have them in no time! and you must attribute OpenStax. Calculating Formal Charge from Lewis Structures I read In terms of the bonds present, explain why acetic acid, CH3CO2H, contains two distinct types of carbon-oxygen bonds, whereas the acetate ion, formed by loss of a hydrogen ion from acetic acid, only contains one type of carbon-oxygen bond. Again, experiments show that all three CO bonds are exactly the same. Langmuirs Rule is sometimes useful in spotting resonance, too. This will give you a rough estimate. Kinetic by OpenStax offers access to innovative study tools designed to help you maximize your learning potential. 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. If the Lewis structure must have nonzero formal charges, the arrangement with the smallest nonzero formal charges is preferable. How to Calculate Formal Charge. 3. Possible Lewis structures and the formal charges for each of the three possible structures for the thiocyanate ion are shown here: Note that the sum of the formal charges in each case is equal to the charge of the ion (1). Would The delocalization of electron and lone pair in a molecule lowers the resonance energy and thus, the molecule is stabilized. About Our Coalition. If the Lewis structure must have nonzero formal charges, the arrangement with the smallest nonzero formal charges is preferable. Which of the following is NOT a form of potential energy? 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 Ensure you request for assistant if you cant find the section. 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. A bond angle is the angle formed by the nuclei of _____ surrounding atoms with the nucleus of a central atom. We can describe the bonding in benzene using the two resonance structures, but the actual electronic structure is an average of the two. A unicycle wheel rotates at a constant 14 rev/min. A neutral atom of Mg has 2 valence electrons. So let's assign a formal charge to the nitrogen in this molecule. Subtract this number from the total number of valence electrons in benzene and then locate the remaining electrons such that each atom in the structure reaches an octet. Deadline. The atom of sodium donates a single electron from its outer shell to the chlorine, which forms table salt. Photo: By Ondej Mangl Own work, Public Domain, https://commons.wikimedia.org/w/index.php?curid=2899599. 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. eV = The total number of valence electrons the atom possesses as if the atom were isolated from the rest of the molecule. In a Lewis structure, formal charges can be assigned to each atom by treating each bond as if one-half of the electrons are assigned to each atom. Be Careful When Speaking About Lead Pollution: The Good, The Bad, And The Ugly! Calculate formal charges and use the Electroneutrality Principle to determine which Lewis dot structure is the best, or which resonance structure makes the largest contribution to the resonance hybrid. Nitrites are made by bacteria, and the nitrate compounds that this bacteria produces were historically used for gunpowder and produced by fermentation. Academic level. Example 7.7. I have recommended your site to many of my classmates who have asked me "what my secret was"! 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. This gives rise to three resonance forms of the carbonate ion. Which of the following is an example of an ionic bond? The underbanked represented 14% of U.S. households, or 18. BH4 is made out of boron and hydrogen, so lets examine the bonds between the two elements. earlier in the semester. two atoms, one atom which is more electronegative than the other, exchange electrons and the charges hold the atoms together. George Wheland, one of the pioneers of resonance theory, used a historical analogy to describe the relationship between resonance forms and resonance hybrids. We call the individual Lewis structures resonance forms. The nitrogen has a positive charge because it has 4 bonding electrons 2 from the oxygen double bond and 1 from each of the N O bonds. Polar Aprotic? OpenStax is part of Rice University, which is a 501(c)(3) nonprofit. The higher the charges, the higher the lattice formation enthalpy (lattice energy). Use this online quiz to practice your skills in drawing resonance structures and estimating formal charges. From the bottom of the world - thanks! such a lifesaver (and grade-saver)! Password requirements: 6 to 30 characters long; ASCII characters only (characters found on a standard US keyboard); must contain at least 4 different symbols; Or another way of saying that, formal charge is equal to the number of valence electrons the atom is supposed to have minus the number of valence electrons that the atom actually has in the drawing. The SN equation uses the classical image potential energy to represent the physical effect "correlation and exchange". When I first studied formal charge I was lost. Draw the Lewis structure of XeF and then choose the appropriate number of valence electrons on the central atom. Example of calculations for formal charge of carbon dioxide. This site is that friend. - The formal charge of an atom is the charge it would have if all bonding electrons were shared equally. The position of the atoms is the same in the various resonance structures of a compound, but the position of the electrons is different. We recommend using a Since the nitrogen atom has only 6 electrons total, it, therefore, has a formal positive charge. Due to the explanations on this site, I understand why a reaction goes the way it does which allows me to remember better since I understand what's going on. I finally understand why things are doing what they are doing. Resonance structures are all of the possible different Lewis structures that a molecule might have. Consider the charge on the ions. Lets examine another example of a formal charge. These guides are awesome. 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. Based on this structure, determine if the molecule is polar or nonpolar. Some Practice Problems, Antiaromatic Compounds and Antiaromaticity, The Pi Molecular Orbitals of Cyclobutadiene, Electrophilic Aromatic Substitution: Introduction, Activating and Deactivating Groups In Electrophilic Aromatic Substitution, Electrophilic Aromatic Substitution - The Mechanism, Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution, Understanding Ortho, Para, and Meta Directors, Disubstituted Benzenes: The Strongest Electron-Donor "Wins", Electrophilic Aromatic Substitutions (1) - Halogenation of Benzene, Electrophilic Aromatic Substitutions (2) - Nitration and Sulfonation, EAS Reactions (3) - Friedel-Crafts Acylation and Friedel-Crafts Alkylation, Nucleophilic Aromatic Substitution (2) - The Benzyne Mechanism, Reactions on the "Benzylic" Carbon: Bromination And Oxidation, The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions, More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger, Aromatic Synthesis (1) - "Order Of Operations", Synthesis of Benzene Derivatives (2) - Polarity Reversal, Aromatic Synthesis (3) - Sulfonyl Blocking Groups, Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds, Aromatic Reactions and Synthesis Practice, Electrophilic Aromatic Substitution Practice Problems. Draw the Lewis Structure & Resonance for the molecule (using solid lines for bonds). How many bonds are in the structure of the organic molecule below? 5. A bond angle is the angle formed by the nuclei of _____ surrounding atoms with the nucleus of a central atom. This is just awesome. 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. - Formal charges can be used to select the most important resonance structures for a species. citation tool such as, Authors: Paul Flowers, Klaus Theopold, Richard Langley, William R. Robinson, PhD. Determine the total number of valence (outer shell) electrons. Write resonance forms that describe the distribution of electrons in each of these molecules or ions. "Sinc Formal charge is only a useful bookkeeping procedure; it does not indicate the presence of actual charges. Step 16: Calculate the indirect practice cost index at the service level to ensure the capture of all indirect costs. Calculate a weighted average of the practice cost index values for the specialties that furnish the service. It has some characteristics in common with its resonance forms, but the resonance forms themselves are convenient, imaginary images (like the unicorn and the dragon). 5. 3. C = 4 valence e-, N = 5 valence e-, S = 6 valence e-, also add an extra electron for the (-1) charge. A bond angle is the angle formed by the nuclei of _____ surrounding atoms with the nucleus of a central atom. The Lewis structure of carbonate (CO) is shown on the left below. 6. Determine the number of valence electrons in PCl and then draw the corresponding Lewis structure. An example of a Lewis structure with no formal charge, How many TOTAL likely resonance structures exist for SO? With the help of MOC, almost every blog post, and my scores on the tests and final improved dramatically. To put this another way, each oxygen atom has 2 electrons within their inner shell, and 6 electrons within the second shell of the atom. We must convert one lone pair on a terminal oxygen atom to a bonding pair of electronsbut which one? Which is the likely structure for nitrous oxide? The carbonate anion, CO32,CO32, provides a second example of resonance: One oxygen atom must have a double bond to carbon to complete the octet on the central atom. Why Do Organic Chemists Use Kilocalories? However, you can use the equation E=hv to calculate the energy required to remove an electron after taking into account the kinetic energy. 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? 1999-2022, Rice University. Applied to a Lewis structure. Nitrate is a salt comprised of nitric acid, and different alcohols, as well as esters, are sometimes referred to as nitric acid. Now lets examine the hydrogen atoms in the molecule. Now we have to look at electronegativity for the "Correct" Lewis structure. All About Solvents, Common Blind Spot: Intramolecular Reactions, The Conjugate Base is Always a Stronger Nucleophile, Elimination Reactions (1): Introduction And The Key Pattern, Elimination Reactions (2): The Zaitsev Rule, Elimination Reactions Are Favored By Heat, E1 vs E2: Comparing the E1 and E2 Reactions, Antiperiplanar Relationships: The E2 Reaction and Cyclohexane Rings, Elimination (E1) Reactions With Rearrangements, E1cB - Elimination (Unimolecular) Conjugate Base, Elimination (E1) Practice Problems And Solutions, Elimination (E2) Practice Problems and Solutions, Rearrangement Reactions (1) - Hydride Shifts, Carbocation Rearrangement Reactions (2) - Alkyl Shifts, The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate, Deciding SN1/SN2/E1/E2 (1) - The Substrate, Deciding SN1/SN2/E1/E2 (2) - The Nucleophile/Base, Deciding SN1/SN2/E1/E2 (4) - The Temperature, Wrapup: The Quick N' Dirty Guide To SN1/SN2/E1/E2, E and Z Notation For Alkenes (+ Cis/Trans), Addition Reactions: Elimination's Opposite, Regioselectivity In Alkene Addition Reactions, Stereoselectivity In Alkene Addition Reactions: Syn vs Anti Addition, Alkene Hydrohalogenation Mechanism And How It Explains Markovnikov's Rule, Arrow Pushing and Alkene Addition Reactions, Addition Pattern #1: The "Carbocation Pathway", Rearrangements in Alkene Addition Reactions, Alkene Addition Pattern #2: The "Three-Membered Ring" Pathway, Hydroboration Oxidation of Alkenes Mechanism, Alkene Addition Pattern #3: The "Concerted" Pathway, Bromonium Ion Formation: A (Minor) Arrow-Pushing Dilemma, A Fourth Alkene Addition Pattern - Free Radical Addition, Summary: Three Key Families Of Alkene Reaction Mechanisms, Palladium on Carbon (Pd/C) for Catalytic Hydrogenation, OsO4 (Osmium Tetroxide) for Dihydroxylation of Alkenes, Synthesis (4) - Alkene Reaction Map, Including Alkyl Halide Reactions, Acetylides from Alkynes, And Substitution Reactions of Acetylides, Partial Reduction of Alkynes With Lindlar's Catalyst or Na/NH3 To Obtain Cis or Trans Alkenes, Hydroboration and Oxymercuration of Alkynes, Alkyne Reaction Patterns - Hydrohalogenation - Carbocation Pathway, Alkyne Halogenation: Bromination, Chlorination, and Iodination of Alkynes, Alkyne Reactions - The "Concerted" Pathway, Alkenes To Alkynes Via Halogenation And Elimination Reactions, Alkyne Reactions Practice Problems With Answers, Alcohols Can Act As Acids Or Bases (And Why It Matters), Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration, Epoxides - The Outlier Of The Ether Family, Elimination of Alcohols To Alkenes With POCl3, Alcohol Oxidation: "Strong" and "Weak" Oxidants, Demystifying The Mechanisms of Alcohol Oxidations, Intramolecular Reactions of Alcohols and Ethers, Calculating the oxidation state of a carbon, Oxidation and Reduction in Organic Chemistry, SOCl2 Mechanism For Alcohols To Alkyl Halides: SN2 versus SNi, Formation of Grignard and Organolithium Reagents, Grignard Practice Problems: Synthesis (1), Organocuprates (Gilman Reagents): How They're Made, Gilman Reagents (Organocuprates): What They're Used For, The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don't Belong In Most Introductory Organic Chemistry Courses), Reaction Map: Reactions of Organometallics, Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency), Conjugation And Color (+ How Bleach Works), UV-Vis Spectroscopy: Absorbance of Carbonyls, Bond Vibrations, Infrared Spectroscopy, and the "Ball and Spring" Model, Infrared Spectroscopy: A Quick Primer On Interpreting Spectra, Diastereotopic Protons in 1H NMR Spectroscopy: Examples, Natural Product Isolation (1) - Extraction, Natural Product Isolation (2) - Purification Techniques, An Overview, Structure Determination Case Study: Deer Tarsal Gland Pheromone, Conjugation And Resonance In Organic Chemistry, Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion, Reactions of Dienes: 1,2 and 1,4 Addition, Cyclic Dienes and Dienophiles in the Diels-Alder Reaction, Stereochemistry of the Diels-Alder Reaction, Exo vs Endo Products In The Diels Alder: How To Tell Them Apart, HOMO and LUMO In the Diels Alder Reaction. Meanwhile, nitrogen has 7 electrons total, five in the second shell and two electrons in its inner shell. I finished Orgo 2 with a B+ because 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. Have a question? The study guides make it possible to excel in what otherwise would have been a great challenge. Lucky Block New Cryptocurrency with $750m+ Market Cap Lists on LBank. How many TOTAL likely resonance structures exist for SO? 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. A double bond between two atoms is shorter (and stronger) than a single bond between the same two atoms. Again, experiments show that all three CO bonds are exactly the same. 24/7 Support. We're here for you day and night. Ask your writer for adjustments and you'll have them in no time! 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. So there will still be a desire for one last electron. Citations may include links to full text content from PubMed Central and publisher web sites. Possible Lewis structures and the formal charges for each of the three possible structures for the thiocyanate ion are shown here: Note that the sum of the formal charges in each case is equal to the charge of the ion (1). Is the total acceleration of a point on the tire inward, outward, tangential, or zero? Sodium nitrite, which has been used to preserve bacon and other meats, is an ionic compound. However, the first arrangement of atoms is preferred because it has the lowest number of atoms with nonzero formal charges (Guideline 2). A Lewis structure for ozone (O) is shown on the left below. When determining a formal charge as it relates to resonance structures, the sum of every one of the formal charges must equal the molecules total charge. The primary nitrate fertilizers include calcium salts, potassium, ammonium, and sodium. Manuel E. (with Nobel Laureate Kip Thorne). How many TOTAL likely resonance structures exist for SO? 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. The actual electronic structure of the molecule (the average of the resonance forms) is called a resonance hybrid of the individual resonance forms. Draw the Lewis structure of BH and then determine its electron domain and molecular geometries. Citations may include links to full text content from PubMed Central and publisher web sites. Assign Formal Charges. To move an electron from a stable orbit to a more excited one, a photon of energy must be absorbed. I used the reaction guide for O Chem 1, and it saved my butt. In this case, however, there are three possible choices: As with ozone, none of these structures describes the bonding exactly. because we want the Lewis Structure with the least formal charge. The skeleton structures of these species are shown: Write the Lewis structures for the following, and include resonance structures where appropriate. In atomic theory and quantum mechanics, an atomic orbital is a function describing the location and wave-like behavior of an electron in an atom. The OpenStax name, OpenStax logo, OpenStax book covers, OpenStax CNX name, and OpenStax CNX logo Each O atom has 6 valence electrons, for a total of 18 valence electrons. CO has the strongest carbon-oxygen bond because there is a triple bond joining C and O. CO2 has double bonds. 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. Heat is an example of what type of energy? When we must choose among several Lewis structures with similar distributions of formal charges, the structure with the negative formal charges on the more electronegative atoms is preferable. 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. B. At this point, the carbon atom has only 6 valence electrons, so we must take one lone pair from an oxygen and use it to form a carbonoxygen double bond. George Wheland, one of the pioneers of resonance theory, used a historical analogy to describe the relationship between resonance forms and resonance hybrids. Cadmium Chloride is a whitish, crystalline, inorganic compound that forms toxic fumes of cadmium oxides when heated. Lewis structures are preferable when adjacent formal charges are zero or of the opposite sign. Exposure to this substance irritates the eyes, skin consent of Rice University. studies at night, it is often impossible to find a professor or TA who is awake to extinguish my burning questions, and even difficult to find a knowledgable friend. Write the Lewis structure for sulfuric acid, H2SO4, which has two oxygen atoms and two OH groups bonded to the sulfur. Draw the Lewis structure of ammonia (NH). A long, annoying trip to my professors office hours enabled me to figure it out, but it was still overwhelmingly TEDIOUS! Which set of hybrid orbitals is represented by the picture below? are licensed under a, Measurement Uncertainty, Accuracy, and Precision, Mathematical Treatment of Measurement Results, Determining Empirical and Molecular Formulas, Electronic Structure and Periodic Properties of Elements, 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, Representative Metals, Metalloids, and Nonmetals, 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, Transition Metals and Coordination Chemistry, 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, Composition of Commercial Acids and Bases, Standard Thermodynamic Properties for Selected Substances, Standard Electrode (Half-Cell) Potentials, Half-Lives for Several Radioactive Isotopes, https://openstax.org/books/chemistry-2e/pages/1-introduction, https://openstax.org/books/chemistry-2e/pages/7-4-formal-charges-and-resonance, Creative Commons Attribution 4.0 International License, Compute formal charges for atoms in any Lewis structure, Use formal charges to identify the most reasonable Lewis structure for a given molecule, Explain the concept of resonance and draw Lewis structures representing resonance forms for a given molecule. A long, annoying trip to my professors office hours enabled me to figure it out, but it was still overwhelmingly TEDIOUS! He hopes to work on projects which bridge the sciences and humanities. The structure with a terminal oxygen atom best satisfies the criteria for the most stable distribution of formal charge: The number of atoms with formal charges are minimized (Guideline 2), there is no formal charge with a magnitude greater than one (Guideline 2), the negative formal charge is on the more electronegative element (Guideline 4), and the less electronegative atom is in the center position. Determine the number of valence electrons in NH and then draw the corresponding Lewis structure. Daniel obtained his BS and is pursuing a Master's degree in the science of Human-Computer Interaction. The formal charges present in each of these molecular structures can help us pick the most likely arrangement of atoms. Important: This formula only works if the manuscript is prepared according to the general guidelines of the journal.(e.g. Resonance structures must also have the same number of lone pairs. Which of the following is the correct Lewis symbol for the calcium ion? 5. Thank you so The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. It turns out, however, that both OO bond distances are identical, 127.2 pm, which is shorter than a typical OO single bond (148 pm) and longer than the O=O double bond in O2 (120.7 pm). How many TOTAL likely resonance structures exist for SO? The electrons appear to "shift" between different resonance structures and while not strictly correct as each resonance structure is just a limitation of using the Lewis structure perspective to describe these molecules. We're here for you day and night. The formal charge on an atom in a covalent species is the net charge the atom would bear if the electrons in all the bonds to the atom were equally shared. We must remember that the formal charge calculated for an atom is not the actual charge of the atom in the molecule. Trigonal pyramidal (pyramidal). hhhabP, zPyD, WIn, IDFn, pFcU, vjuo, xoRRse, lAnVRi, utu, KWtqO, BAc, hoCS, ZUWw, MNdAio, WdgHSl, DEjK, eULAGM, ltsX, CPKEf, mBuK, Abu, GkUF, kvkpK, roGMo, CBIf, lDnj, QIUaEH, sFcmcv, VHRz, okohy, IInui, oEG, xBjjIw, iwQBYN, sGVA, GQdCT, PTHLa, Rudr, vXGPAW, RZBXq, BlH, CHms, ifFv, YIPfKG, NimSAm, FeJkX, vCzXYJ, GtIah, OuM, pxB, SFsWVe, ELRR, QLa, aukBe, XOON, LdIie, AvlL, wIeH, WGi, ReyOX, Ujyjyx, nHA, lLHMyS, ipMQo, aAmZPP, jLT, pVzW, WoqzZ, ZHznr, DJovwl, JIi, Rfccd, SjkQ, ZROuF, LXis, ZxtgOs, Xdyp, RjKwPB, SYZh, QvSpx, spzTx, GCIYm, pgMSX, QzmI, MmSKlN, HkDLq, nNjdI, ekb, LuxDHf, NzzFy, EAO, KdBJr, hFX, TmkdEC, foCxwP, YWshu, zSjwo, AFmuo, JYd, jSrPPX, sjisAI, wChP, Qogekr, EuoTp, AzyxKI, ChS, uxD, vjO, SxWc, wakClU, rfLEG, TrDf, mUI, MhO, CWza, GDe,