Copper chloride called cuprous chloride, is the lower chloride of copper, with the formula CuCl. The substance is a white solid sparingly soluble in water, but soluble in concentrated hydrochloric acid. Impure samples appear green due to the presence of copper chloride. Copper chloride was first prepared by Robert Boyle in the mid-seventeenth century from mercury chloride and copper metal: HgCl2 + 2 Cu → 2 CuCl + HgIn 1799, J. L. Proust characterized the two different chlorides of copper, he prepared CuCl by heating CuCl2 at red heat in the absence of air, causing it to lose half of its combined chlorine followed by removing residual CuCl2 by washing with water. An acidic solution of CuCl was used for analysis of carbon monoxide content in gases, for example in Hempel's gas apparatus; this application was significant during the time that coal gas was used for heating and lighting, during the nineteenth and early twentieth centuries. Copper chloride is produced industrially by the direct combination of copper metal and chlorine at 450–900 °C: 2 Cu + Cl 2 ⟶ 2 CuCl Copper chloride can be prepared by reducing copper chloride, e.g. with sulfur dioxide or a reducing sugar such as Ascorbic Acid: 2 CuCl 2 + SO 2 + 2 H 2 O ⟶ 2 CuCl + H 2 SO 4 + 2 HCl 2 CuCl 2 + C 6 H 8 O 6 ⟶ 2 CuCl + 2 HCl + C 6 H 6 O 6 Many other reducing agents can be used.
Copper chloride has the cubic zincblende crystal structure at ambient conditions. Upon heating to 408 °C the structure changes to hexagonal. Several other crystalline forms of CuCl appear at high pressures. Copper chloride is a Lewis acid, classified as soft according to the Hard-Soft Acid-Base concept. Thus, it tends to form stable complexes with soft Lewis bases such as triphenylphosphine: CuCl + P3 → 4Although CuCl is insoluble in water, it dissolves in aqueous solutions containing suitable donor molecules, it forms complexes with halide ions, for example forming H3O+ CuCl2− with concentrated hydrochloric acid. It is attacked by CN−, S2O32−, NH3 to give the corresponding complexes. Solutions of CuCl in HCl or NH3 absorb carbon monoxide to form colourless complexes such as the chloride-bridged dimer 2; the same hydrochloric acid solutions react with acetylene gas to form. Ammoniacal solutions of CuCl react with acetylenes to form the explosive copper acetylide, Cu2C2. Complexes of CuCl with alkenes can be prepared by reduction of CuCl2 by sulfur dioxide in the presence of the alkene in alcohol solution.
Complexes with dienes such as 1,5-cyclooctadiene are stable: In absence of other ligands, its aqueous solutions are unstable with respect to disproportionation into Cu and CuCl2. In part for this reason samples in air assume a green coloration; the main use of copper chloride is as a precursor to the fungicide copper oxychloride. For this purpose aqueous copper chloride is generated by comproportionation and air-oxidized: Cu + CuCl2 → 2 CuCl 4 CuCl + O2 + 2 H2O → Cu3Cl24 + CuCl2Copper chloride catalyzes a variety of organic reactions, as discussed above, its affinity for carbon monoxide in the presence of aluminium chloride is exploited in the COPureSM process. CuCl is used with carbon monoxide, aluminium chloride, hydrogen chloride in the Gatterman-Koch reaction to form benzaldehydes. In the Sandmeyer reaction. Treatment of an arenediazonium salt with CuCl leads to an aryl chloride, for example: The reaction has wide scope and gives good yields. Early investigators observed that copper halides catalyse 1,4-addition of Grignard reagents to alpha,beta-unsaturated ketones led to the development of organocuprate reagents that are used today in organic synthesis: This finding led to the development of organocopper chemistry.
For example, CuCl reacts with methyllithium to form "Gilman reagents" such as 2CuLi, which find extensive use in organic synthesis. Grignard reagents form similar organocopper compounds. Although other copper compounds such as copper iodide are now more used for these types of reactions, copper chloride is still recommended in some cases: Here, Bu indicates an n-butyl group. Without CuCl, the Grignard reagent alone gives a mixture of 1,2- and 1,4-addition products. Copper chloride is an intermediate formed from copper chloride in the Wacker process. CuCl is used as a catalyst in Atom Transfer Radical Polymerization. National Pollutant Inventory – Copper and compounds fact sheet The COPureSM Process for purifying CO utilizing a copper chloride complex
Encyclopædia Britannica, Eleventh Edition
The Encyclopædia Britannica, Eleventh Edition is a 29-volume reference work, an edition of the Encyclopædia Britannica. It was developed during the encyclopaedia's transition from a British to an American publication; some of its articles were written by the best-known scholars of the time. This edition of the encyclopedia, containing 40,000 entries, is now in the public domain, many of its articles have been used as a basis for articles in Wikipedia. However, the outdated nature of some of its content makes its use as a source for modern scholarship problematic; some articles have special value and interest to modern scholars as cultural artifacts of the 19th and early 20th centuries. The 1911 eleventh edition was assembled with the management of American publisher Horace Everett Hooper. Hugh Chisholm, who had edited the previous edition, was appointed editor in chief, with Walter Alison Phillips as his principal assistant editor. Hooper bought the rights to the 25-volume 9th edition and persuaded the British newspaper The Times to issue its reprint, with eleven additional volumes as the tenth edition, published in 1902.
Hooper's association with The Times ceased in 1909, he negotiated with the Cambridge University Press to publish the 29-volume eleventh edition. Though it is perceived as a quintessentially British work, the eleventh edition had substantial American influences, not only in the increased amount of American and Canadian content, but in the efforts made to make it more popular. American marketing methods assisted sales; some 14% of the contributors were from North America, a New York office was established to coordinate their work. The initials of the encyclopedia's contributors appear at the end of selected articles or at the end of a section in the case of longer articles, such as that on China, a key is given in each volume to these initials; some articles were written by the best-known scholars of the time, such as Edmund Gosse, J. B. Bury, Algernon Charles Swinburne, John Muir, Peter Kropotkin, T. H. Huxley, James Hopwood Jeans and William Michael Rossetti. Among the lesser-known contributors were some who would become distinguished, such as Ernest Rutherford and Bertrand Russell.
Many articles were carried over from some with minimal updating. Some of the book-length articles were divided into smaller parts for easier reference, yet others much abridged; the best-known authors contributed only a single article or part of an article. Most of the work was done by British Museum scholars and other scholars; the 1911 edition was the first edition of the encyclopædia to include more than just a handful of female contributors, with 34 women contributing articles to the edition. The eleventh edition introduced a number of changes of the format of the Britannica, it was the first to be published complete, instead of the previous method of volumes being released as they were ready. The print type was subject to continual updating until publication, it was the first edition of Britannica to be issued with a comprehensive index volume in, added a categorical index, where like topics were listed. It was the first not to include long treatise-length articles. Though the overall length of the work was about the same as that of its predecessor, the number of articles had increased from 17,000 to 40,000.
It was the first edition of Britannica to include biographies of living people. Sixteen maps of the famous 9th edition of Stielers Handatlas were translated to English, converted to Imperial units, printed in Gotha, Germany by Justus Perthes and became part this edition. Editions only included Perthes' great maps as low quality reproductions. According to Coleman and Simmons, the content of the encyclopedia was distributed as follows: Hooper sold the rights to Sears Roebuck of Chicago in 1920, completing the Britannica's transition to becoming a American publication. In 1922, an additional three volumes, were published, covering the events of the intervening years, including World War I. These, together with a reprint of the eleventh edition, formed the twelfth edition of the work. A similar thirteenth edition, consisting of three volumes plus a reprint of the twelfth edition, was published in 1926, so the twelfth and thirteenth editions were related to the eleventh edition and shared much of the same content.
However, it became apparent that a more thorough update of the work was required. The fourteenth edition, published in 1929, was revised, with much text eliminated or abridged to make room for new topics; the eleventh edition was the basis of every version of the Encyclopædia Britannica until the new fifteenth edition was published in 1974, using modern information presentation. The eleventh edition's articles are still of value and interest to modern readers and scholars as a cultural artifact: the British Empire was at its maximum, imperialism was unchallenged, much of the world was still ruled by monarchs, the tragedy of the modern world wars was still in the future, they are an invaluable resource for topics omitted from modern encyclopedias for biography and the history of science and technology. As a literary text, the encyclopedia has value as an example of early 20th-century prose. For example, it employs literary devices, such as pathetic fallacy, which are not as common in modern reference texts.
In 1917, using the pseudonym of S. S. Van Dine, the US art critic and author Willard Huntington Wright published Misinforming a Nation, a 200+
Cambridge University Press
Cambridge University Press is the publishing business of the University of Cambridge. Granted letters patent by King Henry VIII in 1534, it is the world's oldest publishing house and the second-largest university press in the world, it holds letters patent as the Queen's Printer. The press mission is "to further the University's mission by disseminating knowledge in the pursuit of education and research at the highest international levels of excellence". Cambridge University Press is a department of the University of Cambridge and is both an academic and educational publisher. With a global sales presence, publishing hubs, offices in more than 40 countries, it publishes over 50,000 titles by authors from over 100 countries, its publishing includes academic journals, reference works and English language teaching and learning publications. Cambridge University Press is a charitable enterprise that transfers part of its annual surplus back to the university. Cambridge University Press is both the oldest publishing house in the world and the oldest university press.
It originated from letters patent granted to the University of Cambridge by Henry VIII in 1534, has been producing books continuously since the first University Press book was printed. Cambridge is one of the two privileged presses. Authors published by Cambridge have included John Milton, William Harvey, Isaac Newton, Bertrand Russell, Stephen Hawking. University printing began in Cambridge when the first practising University Printer, Thomas Thomas, set up a printing house on the site of what became the Senate House lawn – a few yards from where the press's bookshop now stands. In those days, the Stationers' Company in London jealously guarded its monopoly of printing, which explains the delay between the date of the university's letters patent and the printing of the first book. In 1591, Thomas's successor, John Legate, printed the first Cambridge Bible, an octavo edition of the popular Geneva Bible; the London Stationers objected strenuously. The university's response was to point out the provision in its charter to print "all manner of books".
Thus began the press's tradition of publishing the Bible, a tradition that has endured for over four centuries, beginning with the Geneva Bible, continuing with the Authorized Version, the Revised Version, the New English Bible and the Revised English Bible. The restrictions and compromises forced upon Cambridge by the dispute with the London Stationers did not come to an end until the scholar Richard Bentley was given the power to set up a'new-style press' in 1696. In July 1697 the Duke of Somerset made a loan of £200 to the university "towards the printing house and presse" and James Halman, Registrary of the University, lent £100 for the same purpose, it was in Bentley's time, in 1698, that a body of senior scholars was appointed to be responsible to the university for the press's affairs. The Press Syndicate's publishing committee still meets and its role still includes the review and approval of the press's planned output. John Baskerville became University Printer in the mid-eighteenth century.
Baskerville's concern was the production of the finest possible books using his own type-design and printing techniques. Baskerville wrote, "The importance of the work demands all my attention. Caxton would have found nothing to surprise him if he had walked into the press's printing house in the eighteenth century: all the type was still being set by hand. A technological breakthrough was badly needed, it came when Lord Stanhope perfected the making of stereotype plates; this involved making a mould of the whole surface of a page of type and casting plates from that mould. The press was the first to use this technique, in 1805 produced the technically successful and much-reprinted Cambridge Stereotype Bible. By the 1850s the press was using steam-powered machine presses, employing two to three hundred people, occupying several buildings in the Silver Street and Mill Lane area, including the one that the press still occupies, the Pitt Building, built for the press and in honour of William Pitt the Younger.
Under the stewardship of C. J. Clay, University Printer from 1854 to 1882, the press increased the size and scale of its academic and educational publishing operation. An important factor in this increase was the inauguration of its list of schoolbooks. During Clay's administration, the press undertook a sizeable co-publishing venture with Oxford: the Revised Version of the Bible, begun in 1870 and completed in 1885, it was in this period as well that the Syndics of the press turned down what became the Oxford English Dictionary—a proposal for, brought to Cambridge by James Murray before he turned to Oxford. The appointment of R. T. Wright as Secretary of the Press Syndicate in 1892 marked the beginning of the press's development as a modern publishing business with a defined editorial policy and administrative structure, it was Wright who devised the plan for one of the most distinctive Cambridge contributions to publishing—the Cambridge Histories. The Cambridge Modern History was published
The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding environmental pressure. A liquid in a partial vacuum has a lower boiling point than when that liquid is at atmospheric pressure. A liquid at high pressure has a higher boiling point than when that liquid is at atmospheric pressure. For example, water at 93.4 °C at 1,905 metres altitude. For a given pressure, different liquids will boil at different temperatures; the normal boiling point of a liquid is the special case in which the vapor pressure of the liquid equals the defined atmospheric pressure at sea level, 1 atmosphere. At that temperature, the vapor pressure of the liquid becomes sufficient to overcome atmospheric pressure and allow bubbles of vapor to form inside the bulk of the liquid; the standard boiling point has been defined by IUPAC since 1982 as the temperature at which boiling occurs under a pressure of 1 bar.
The heat of vaporization is the energy required to transform a given quantity of a substance from a liquid into a gas at a given pressure. Liquids may change to a vapor at temperatures below their boiling points through the process of evaporation. Evaporation is a surface phenomenon in which molecules located near the liquid's edge, not contained by enough liquid pressure on that side, escape into the surroundings as vapor. On the other hand, boiling is a process in which molecules anywhere in the liquid escape, resulting in the formation of vapor bubbles within the liquid. A saturated liquid contains as much thermal energy. Saturation temperature means boiling point; the saturation temperature is the temperature for a corresponding saturation pressure at which a liquid boils into its vapor phase. The liquid can be said to be saturated with thermal energy. Any addition of thermal energy results in a phase transition. If the pressure in a system remains constant, a vapor at saturation temperature will begin to condense into its liquid phase as thermal energy is removed.
A liquid at saturation temperature and pressure will boil into its vapor phase as additional thermal energy is applied. The boiling point corresponds to the temperature at which the vapor pressure of the liquid equals the surrounding environmental pressure. Thus, the boiling point is dependent on the pressure. Boiling points may be published with respect to the NIST, USA standard pressure of 101.325 kPa, or the IUPAC standard pressure of 100.000 kPa. At higher elevations, where the atmospheric pressure is much lower, the boiling point is lower; the boiling point increases with increased pressure up to the critical point, where the gas and liquid properties become identical. The boiling point cannot be increased beyond the critical point; the boiling point decreases with decreasing pressure until the triple point is reached. The boiling point cannot be reduced below the triple point. If the heat of vaporization and the vapor pressure of a liquid at a certain temperature are known, the boiling point can be calculated by using the Clausius–Clapeyron equation, thus: T B = − 1, where: T B is the boiling point at the pressure of interest, R is the ideal gas constant, P is the vapour pressure of the liquid at the pressure of interest, P 0 is some pressure where the corresponding T 0 is known, Δ H vap is the heat of vaporization of the liquid, T 0 is the boiling temperature, ln is the natural logarithm.
Saturation pressure is the pressure for a corresponding saturation temperature at which a liquid boils into its vapor phase. Saturation pressure and saturation temperature have a direct relationship: as saturation pressure is increased, so is saturation temperature. If the temperature in a system remains constant, vapor at saturation pressure and temperature will begin to condense into its liquid phase as the system pressure is increased. A liquid at saturation pressure and temperature will tend to flash into its vapor phase as system pressure is decreased. There are two conventions regarding the standard boiling point of water: The normal boiling point is 99.97 °C at a pressure of 1 atm. The IUPAC recommended standard boiling point of water at a standard pressure of 100 kPa is 99.61 °C. For comparison, on top of Mount Everest, at 8,848 m elevation, the pressure is about 34 kPa and the boiling point of water is 71 °C; the Celsius temperature scale was defined until 1954 by two points: 0 °C being defined by the wate
Precipitation is the creation of a solid from a solution. When the reaction occurs in a liquid solution, the solid formed is called the'precipitate'; the chemical that causes the solid to form is called the'precipitant'. Without sufficient force of gravity to bring the solid particles together, the precipitate remains in suspension. After sedimentation when using a centrifuge to press it into a compact mass, the precipitate may be referred to as a'pellet'. Precipitation can be used as a medium; the precipitate-free liquid remaining above the solid is called the'supernate' or'supernatant'. Powders derived from precipitation have historically been known as'flowers'; when the solid appears in the form of cellulose fibers which have been through chemical processing, the process is referred to as regeneration. Sometimes the formation of a precipitate indicates the occurrence of a chemical reaction. If silver nitrate solution is poured into a solution of sodium chloride, a chemical reaction occurs forming a white precipitate of silver chloride.
When potassium iodide solution reacts with lead nitrate solution, a yellow precipitate of lead iodide is formed. Precipitation may occur. Precipitation may occur from a supersaturated solution. In solids, precipitation occurs if the concentration of one solid is above the solubility limit in the host solid, due to e.g. rapid quenching or ion implantation, the temperature is high enough that diffusion can lead to segregation into precipitates. Precipitation in solids is used to synthesize nanoclusters. An important stage of the precipitation process is the onset of nucleation; the creation of a hypothetical solid particle includes the formation of an interface, which requires some energy based on the relative surface energy of the solid and the solution. If this energy is not available, no suitable nucleation surface is available, supersaturation occurs. Precipitation reactions can be used for making pigments, removing salts from water in water treatment, in classical qualitative inorganic analysis.
Precipitation is useful to isolate the products of a reaction during workup. Ideally, the product of the reaction is insoluble in the reaction solvent. Thus, it precipitates. An example of this would be the synthesis of porphyrins in refluxing propionic acid. By cooling the reaction mixture to room temperature, crystals of the porphyrin precipitate, are collected by filtration: Precipitation may occur when an antisolvent is added, drastically reducing the solubility of the desired product. Thereafter, the precipitate may be separated by filtration, decanting, or centrifugation. An example would be the synthesis of chromic tetraphenylporphyrin chloride: water is added to the DMF reaction solution, the product precipitates. Precipitation is useful in purifying products: crude bmim-Cl is taken up in acetonitrile, dropped into ethyl acetate, where it precipitates. Another important application of an antisolvent is in ethanol precipitation of DNA. In metallurgy, precipitation from a solid solution is a useful way to strengthen alloys.
An example of a precipitation reaction: Aqueous silver nitrate is added to a solution containing potassium chloride, the precipitation of a white solid, silver chloride, is observed. AgNO 3 + KCl ⟶ AgCl ↓ + KNO 3 The silver chloride has formed a solid, observed as a precipitate; this reaction can be written emphasizing the dissociated ions in a combined solution. This is known as the ionic equation. Ag + + NO 3 − + K + + Cl − ⟶ AgCl ↓ + K + + NO 3 − A final way to represent a precipitate reaction is known as a net ionic reaction. Many compounds containing metal ions produce precipitates with distinctive colors; the following are typical colors for various metals. However, many of these compounds can produce colors different from those listed. Other compounds form white precipitates. Precipitate formation is useful in the detection of the type of cation in a salt. To do this, an alkali first reacts with the unknown salt to produce a precipitate, the hydroxide of the unknown salt. To identify the cation, the color of the precipitate and its solubility in excess are noted.
Similar processes are used in sequence – for example, a barium nitrate solution will react with sulfate ions to form a solid barium sulfate precipitate, indicating that it is that sulfate ions are present. Digestion, or precipitate ageing, happens when a freshly formed precipitate is left at a higher temperature, in the solution from which it precipitates, it results in bigger particles. The physico-chemical process underlying digestion is called Ostwald ripening. Coprecipitation Salting in Salting out Effervescence Zumdahl, Steven S.. Chemical Principles. New York: Houghton Mifflin. ISBN 0-618-37206-7. Precipitation reactions of certain cations Digestion Instruments A Thesis on pattern formation in precipitation reactions
Silver nitrate is an inorganic compound with chemical formula AgNO3. This compound is a versatile precursor to many other silver compounds, such as those used in photography, it is far less sensitive to light than the halides. It was once called lunar caustic because silver was called luna by the ancient alchemists, who believed that silver was associated with the moon. In solid silver nitrate, the silver ions are three-coordinated in a trigonal planar arrangement. Albertus Magnus, in the 13th century, documented the ability of nitric acid to separate gold and silver by dissolving the silver. Magnus noted. Silver nitrate can be prepared by reacting silver, such as a silver bullion or silver foil, with nitric acid, resulting in silver nitrate and oxides of nitrogen. Reaction byproducts depend upon the concentration of nitric acid used. 3 Ag + 4 HNO3 → 3 AgNO3 + 2 H2O + NO Ag + 2 HNO3 → AgNO3 + H2O + NO2This is performed under a fume hood because of toxic nitrogen oxides evolved during the reaction.
A typical reaction with silver nitrate is to suspend a rod of copper in a solution of silver nitrate and leave it for a few hours. The silver nitrate reacts with copper to form hairlike crystals of silver metal and a blue solution of copper nitrate: 2 AgNO3 + Cu → Cu2 + 2 AgSilver nitrate decomposes when heated: 2 AgNO3 → 2 Ag + O2 + 2 NO2Qualitatively, decomposition is negligible below the melting point, but becomes appreciable around 250 °C and decompose at 440 °C. Most metal nitrates thermally decompose to the respective oxides, but silver oxide decomposes at a lower temperature than silver nitrate, so the decomposition of silver nitrate yields elemental silver instead. Silver nitrate is the least expensive salt of silver, it is non-hygroscopic, in contrast to silver silver perchlorate. It is stable to light, it dissolves in numerous solvents, including water. The nitrate can be replaced by other ligands, rendering AgNO3 versatile. Treatment with solutions of halide ions gives a precipitate of AgX.
When making photographic film, silver nitrate is treated with halide salts of sodium or potassium to form insoluble silver halide in situ in photographic gelatin, applied to strips of tri-acetate or polyester. Silver nitrate is used to prepare some silver-based explosives, such as the fulminate, azide, or acetylide, through a precipitation reaction. Treatment of silver nitrate with base gives dark grey silver oxide: 2 AgNO3 + 2 NaOH → Ag2O + 2 NaNO3 + H2O The silver cation, Ag+, reacts with halide sources to produce the insoluble silver halide, a cream precipitate if Br- is used, a white precipitate if Cl− is used and a yellow precipitate if I− is used; this reaction is used in inorganic chemistry to abstract halides: Ag+ + X− → AgXwhere X− = Cl−, Br−, or I−. Other silver salts with non-coordinating anions, namely silver tetrafluoroborate and silver hexafluorophosphate are used for more demanding applications; this reaction is used in analytical chemistry to confirm the presence of chloride, bromide, or iodide ions.
Samples are acidified with dilute nitric acid to remove interfering ions, e.g. carbonate ions and sulfide ions. This step avoids confusion of silver sulfide or silver carbonate precipitates with that of silver halides; the color of precipitate varies with the halide: yellow. AgBr and AgI photo-decompose to the metal, as evidence by a grayish color on exposed samples; the same reaction was used on steamships in order to determine whether or not boiler feedwater had been contaminated with seawater. It is still used to determine if moisture on dry cargo is a result of condensation from humid air, or from seawater leaking through the hull. Silver nitrate is used in many ways in e.g. for deprotection and oxidations. Ag+ binds alkenes reversibly, silver nitrate has been used to separate mixtures of alkenes by selective absorption; the resulting adduct can be decomposed with ammonia to release the free alkene. Silver Nitrate is soluble in water but is poorly soluble in most organic solvents, except acetonitrile.
In histology, silver nitrate is used for silver staining, for demonstrating reticular fibers and nucleic acids. For this reason it is used to demonstrate proteins in PAGE gels, it can be used as a stain in scanning electron microscopy. Silver salts have antiseptic properties. In 1881 Credé introduced the use of dilute solutions of AgNO3 in newborn babies' eyes at birth to prevent contraction of gonorrhea from the mother, which could cause blindness. Fused silver nitrate, shaped into sticks, was traditionally called "lunar caustic", it is used as a cauterizing agent, for example to remove granulation tissue around a stoma. General Sir James Abbott noted in his journals that in India in 1827 it was infused by a British surgeon into wounds in his arm resulting from the bite of a mad dog to cauterize the wounds and prevent the onset of rabies. Silver nitrate is used to cauterize superficial blood vessels in the nose to help prevent nose bleeds. Dentists sometimes use silver nitrate-infused swabs to heal oral ulcers.
Silver nitrate is used by some podiatrists to kill cells located in the nail bed. The Canadian physician C. A. Douglas Ringrose researched the use of silver nitrate for sterilization procedures, believing that silver nitrate could be used to block and corrode the fallopian tubes; the technique was ineffective. Much research has been done in evaluating the
Simplified molecular-input line-entry system
The simplified molecular-input line-entry system is a specification in the form of a line notation for describing the structure of chemical species using short ASCII strings. SMILES strings can be imported by most molecule editors for conversion back into two-dimensional drawings or three-dimensional models of the molecules; the original SMILES specification was initiated in the 1980s. It has since been extended. In 2007, an open standard called. Other linear notations include the Wiswesser line notation, ROSDAL, SYBYL Line Notation; the original SMILES specification was initiated by David Weininger at the USEPA Mid-Continent Ecology Division Laboratory in Duluth in the 1980s. Acknowledged for their parts in the early development were "Gilman Veith and Rose Russo and Albert Leo and Corwin Hansch for supporting the work, Arthur Weininger and Jeremy Scofield for assistance in programming the system." The Environmental Protection Agency funded the initial project to develop SMILES. It has since been modified and extended by others, most notably by Daylight Chemical Information Systems.
In 2007, an open standard called "OpenSMILES" was developed by the Blue Obelisk open-source chemistry community. Other'linear' notations include the Wiswesser Line Notation, ROSDAL and SLN. In July 2006, the IUPAC introduced the InChI as a standard for formula representation. SMILES is considered to have the advantage of being more human-readable than InChI; the term SMILES refers to a line notation for encoding molecular structures and specific instances should be called SMILES strings. However, the term SMILES is commonly used to refer to both a single SMILES string and a number of SMILES strings; the terms "canonical" and "isomeric" can lead to some confusion when applied to SMILES. The terms are not mutually exclusive. A number of valid SMILES strings can be written for a molecule. For example, CCO, OCC and CC all specify the structure of ethanol. Algorithms have been developed to generate the same SMILES string for a given molecule; this SMILES is unique for each structure, although dependent on the canonicalization algorithm used to generate it, is termed the canonical SMILES.
These algorithms first convert the SMILES to an internal representation of the molecular structure. Various algorithms for generating canonical SMILES have been developed and include those by Daylight Chemical Information Systems, OpenEye Scientific Software, MEDIT, Chemical Computing Group, MolSoft LLC, the Chemistry Development Kit. A common application of canonical SMILES is indexing and ensuring uniqueness of molecules in a database; the original paper that described the CANGEN algorithm claimed to generate unique SMILES strings for graphs representing molecules, but the algorithm fails for a number of simple cases and cannot be considered a correct method for representing a graph canonically. There is no systematic comparison across commercial software to test if such flaws exist in those packages. SMILES notation allows the specification of configuration at tetrahedral centers, double bond geometry; these are structural features that cannot be specified by connectivity alone and SMILES which encode this information are termed isomeric SMILES.
A notable feature of these rules is. The term isomeric SMILES is applied to SMILES in which isotopes are specified. In terms of a graph-based computational procedure, SMILES is a string obtained by printing the symbol nodes encountered in a depth-first tree traversal of a chemical graph; the chemical graph is first trimmed to remove hydrogen atoms and cycles are broken to turn it into a spanning tree. Where cycles have been broken, numeric suffix labels are included to indicate the connected nodes. Parentheses are used to indicate points of branching on the tree; the resultant SMILES form depends on the choices: of the bonds chosen to break cycles, of the starting atom used for the depth-first traversal, of the order in which branches are listed when encountered. Atoms are represented by the standard abbreviation of the chemical elements, in square brackets, such as for gold. Brackets may be omitted in the common case of atoms which: are in the "organic subset" of B, C, N, O, P, S, F, Cl, Br, or I, have no formal charge, have the number of hydrogens attached implied by the SMILES valence model, are the normal isotopes, are not chiral centers.
All other elements must be enclosed in brackets, have charges and hydrogens shown explicitly. For instance, the SMILES for water may be written as either O or. Hydrogen may be written as a separate atom; when brackets are used, the symbol H is added if the atom in brackets is bonded to one or more hydrogen, followed by the number of hydrogen atoms if greater than 1 by the sign + for a positive charge or by - for a negative charge. For example, for ammonium. If there is more than one charge, it is written as digit.