The melting point of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium; the melting point of a substance depends on pressure and is specified at a standard pressure such as 1 atmosphere or 100 kPa. When considered as the temperature of the reverse change from liquid to solid, it is referred to as the freezing point or crystallization point; because of the ability of some substances to supercool, the freezing point is not considered as a characteristic property of a substance. When the "characteristic freezing point" of a substance is determined, in fact the actual methodology is always "the principle of observing the disappearance rather than the formation of ice", that is, the melting point. For most substances and freezing points are equal. For example, the melting point and freezing point of mercury is 234.32 kelvins. However, certain substances possess differing solid-liquid transition temperatures.
For example, agar melts at 85 °C and solidifies from 31 °C. The melting point of ice at 1 atmosphere of pressure is close to 0 °C. In the presence of nucleating substances, the freezing point of water is not always the same as the melting point. In the absence of nucleators water can exist as a supercooled liquid down to −48.3 °C before freezing. The chemical element with the highest melting point is tungsten, at 3,414 °C; the often-cited carbon does not melt at ambient pressure but sublimes at about 3,726.85 °C. Tantalum hafnium carbide is a refractory compound with a high melting point of 4215 K. At the other end of the scale, helium does not freeze at all at normal pressure at temperatures arbitrarily close to absolute zero. Many laboratory techniques exist for the determination of melting points. A Kofler bench is a metal strip with a temperature gradient. Any substance can be placed on a section of the strip, revealing its thermal behaviour at the temperature at that point. Differential scanning calorimetry gives information on melting point together with its enthalpy of fusion.
A basic melting point apparatus for the analysis of crystalline solids consists of an oil bath with a transparent window and a simple magnifier. The several grains of a solid are placed in a thin glass tube and immersed in the oil bath; the oil bath is heated and with the aid of the magnifier melting of the individual crystals at a certain temperature can be observed. In large/small devices, the sample is placed in a heating block, optical detection is automated; the measurement can be made continuously with an operating process. For instance, oil refineries measure the freeze point of diesel fuel online, meaning that the sample is taken from the process and measured automatically; this allows for more frequent measurements as the sample does not have to be manually collected and taken to a remote laboratory. For refractory materials the high melting point may be determined by heating the material in a black body furnace and measuring the black-body temperature with an optical pyrometer. For the highest melting materials, this may require extrapolation by several hundred degrees.
The spectral radiance from an incandescent body is known to be a function of its temperature. An optical pyrometer matches the radiance of a body under study to the radiance of a source, calibrated as a function of temperature. In this way, the measurement of the absolute magnitude of the intensity of radiation is unnecessary. However, known temperatures must be used to determine the calibration of the pyrometer. For temperatures above the calibration range of the source, an extrapolation technique must be employed; this extrapolation is accomplished by using Planck's law of radiation. The constants in this equation are not known with sufficient accuracy, causing errors in the extrapolation to become larger at higher temperatures. However, standard techniques have been developed to perform this extrapolation. Consider the case of using gold as the source. In this technique, the current through the filament of the pyrometer is adjusted until the light intensity of the filament matches that of a black-body at the melting point of gold.
This establishes the primary calibration temperature and can be expressed in terms of current through the pyrometer lamp. With the same current setting, the pyrometer is sighted on another black-body at a higher temperature. An absorbing medium of known transmission is inserted between this black-body; the temperature of the black-body is adjusted until a match exists between its intensity and that of the pyrometer filament. The true higher temperature of the black-body is determined from Planck's Law; the absorbing medium is removed and the current through the filament is adjusted to match the filament intensity to that of the black-body. This establishes a second calibration point for the pyrometer; this step is repeated to carry the calibration to hi
International Standard Serial Number
An International Standard Serial Number is an eight-digit serial number used to uniquely identify a serial publication, such as a magazine. The ISSN is helpful in distinguishing between serials with the same title. ISSN are used in ordering, interlibrary loans, other practices in connection with serial literature; the ISSN system was first drafted as an International Organization for Standardization international standard in 1971 and published as ISO 3297 in 1975. ISO subcommittee TC 46/SC 9 is responsible for maintaining the standard; when a serial with the same content is published in more than one media type, a different ISSN is assigned to each media type. For example, many serials are published both in electronic media; the ISSN system refers to these types as electronic ISSN, respectively. Conversely, as defined in ISO 3297:2007, every serial in the ISSN system is assigned a linking ISSN the same as the ISSN assigned to the serial in its first published medium, which links together all ISSNs assigned to the serial in every medium.
The format of the ISSN is an eight digit code, divided by a hyphen into two four-digit numbers. As an integer number, it can be represented by the first seven digits; the last code digit, which may be 0-9 or an X, is a check digit. Formally, the general form of the ISSN code can be expressed as follows: NNNN-NNNC where N is in the set, a digit character, C is in; the ISSN of the journal Hearing Research, for example, is 0378-5955, where the final 5 is the check digit, C=5. To calculate the check digit, the following algorithm may be used: Calculate the sum of the first seven digits of the ISSN multiplied by its position in the number, counting from the right—that is, 8, 7, 6, 5, 4, 3, 2, respectively: 0 ⋅ 8 + 3 ⋅ 7 + 7 ⋅ 6 + 8 ⋅ 5 + 5 ⋅ 4 + 9 ⋅ 3 + 5 ⋅ 2 = 0 + 21 + 42 + 40 + 20 + 27 + 10 = 160 The modulus 11 of this sum is calculated. For calculations, an upper case X in the check digit position indicates a check digit of 10. To confirm the check digit, calculate the sum of all eight digits of the ISSN multiplied by its position in the number, counting from the right.
The modulus 11 of the sum must be 0. There is an online ISSN checker. ISSN codes are assigned by a network of ISSN National Centres located at national libraries and coordinated by the ISSN International Centre based in Paris; the International Centre is an intergovernmental organization created in 1974 through an agreement between UNESCO and the French government. The International Centre maintains a database of all ISSNs assigned worldwide, the ISDS Register otherwise known as the ISSN Register. At the end of 2016, the ISSN Register contained records for 1,943,572 items. ISSN and ISBN codes are similar in concept. An ISBN might be assigned for particular issues of a serial, in addition to the ISSN code for the serial as a whole. An ISSN, unlike the ISBN code, is an anonymous identifier associated with a serial title, containing no information as to the publisher or its location. For this reason a new ISSN is assigned to a serial each time it undergoes a major title change. Since the ISSN applies to an entire serial a new identifier, the Serial Item and Contribution Identifier, was built on top of it to allow references to specific volumes, articles, or other identifiable components.
Separate ISSNs are needed for serials in different media. Thus, the print and electronic media versions of a serial need separate ISSNs. A CD-ROM version and a web version of a serial require different ISSNs since two different media are involved. However, the same ISSN can be used for different file formats of the same online serial; this "media-oriented identification" of serials made sense in the 1970s. In the 1990s and onward, with personal computers, better screens, the Web, it makes sense to consider only content, independent of media; this "content-oriented identification" of serials was a repressed demand during a decade, but no ISSN update or initiative occurred. A natural extension for ISSN, the unique-identification of the articles in the serials, was the main demand application. An alternative serials' contents model arrived with the indecs Content Model and its application, the digital object identifier, as ISSN-independent initiative, consolidated in the 2000s. Only in 2007, ISSN-L was defined in the
Diethyl ether, or ether, is an organic compound in the ether class with the formula 2O, sometimes abbreviated as Et2O. It is a colorless volatile flammable liquid, it is used as a solvent in laboratories and as a starting fluid for some engines. It was used as a general anesthetic, until non-flammable drugs were developed, such as halothane, it has been used as a recreational drug to cause intoxication. Most diethyl ether is produced as a byproduct of the vapor-phase hydration of ethylene to make ethanol; this process uses solid-supported phosphoric acid catalysts and can be adjusted to make more ether if the need arises. Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethanol is mixed with a strong acid sulfuric acid, H2SO4; the acid dissociates in the aqueous environment producing hydronium ions, H3O+. A hydrogen ion protonates the electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge: CH3CH2OH + H3O+ → CH3CH2OH2+ + H2OA nucleophilic oxygen atom of unprotonated ethanol displaces a water molecule from the protonated ethanol molecule, producing water, a hydrogen ion and diethyl ether.
CH3CH2OH2+ + CH3CH2OH → H2O + H+ + CH3CH2OCH2CH3This reaction must be carried out at temperatures lower than 150 °C in order to ensure that an elimination product is not a product of the reaction. At higher temperatures, ethanol will dehydrate to form ethylene; the reaction to make diethyl ether is reversible, so an equilibrium between reactants and products is achieved. Getting a good yield of ether requires that ether be distilled out of the reaction mixture before it reverts to ethanol, taking advantage of Le Chatelier's principle. Another reaction that can be used for the preparation of ethers is the Williamson ether synthesis, in which an alkoxide performs a nucleophilic substitution upon an alkyl halide, it is important as a solvent in the production of cellulose plastics such as cellulose acetate. Diethyl ether has a high cetane number of 85–96 and is used as a starting fluid, in combination with petroleum distillates for gasoline and Diesel engines because of its high volatility and low flash point.
Ether starting fluid is sold and used in countries with cold climates, as it can help with cold starting an engine at sub-zero temperatures. For the same reason it is used as a component of the fuel mixture for carbureted compression ignition model engines. In this way diethyl ether is similar to one of its precursors, ethanol. Diethyl ether is a common laboratory aprotic solvent, it has limited solubility in water and dissolves 1.5 g/100 g water at 25 °C. This, coupled with its high volatility, makes it ideal for use as the non-polar solvent in liquid-liquid extraction; when used with an aqueous solution, the diethyl ether layer is on top as it has a lower density than the water. It is a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents. Due to its application in the manufacturing of illicit substances, it is listed in the Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances as well as substances such as acetone and sulfuric acid.
William T. G. Morton participated in a public demonstration of ether anesthesia on October 16, 1846 at the Ether Dome in Boston, Massachusetts. However, Crawford Williamson Long, is now known to have demonstrated its use as a general anesthetic in surgery to officials in Georgia, as early as March 30, 1842, Long publicly demonstrated ether's use as a surgical anesthetic on six occasions before the Boston demonstration. British doctors were aware of the anesthetic properties of ether as early as 1840 where it was prescribed in conjunction with opium. Diethyl ether supplanted the use of chloroform as a general anesthetic due to ether's more favorable therapeutic index, that is, a greater difference between an effective dose and a toxic dose. Diethyl ether increases tracheobronchial secretions. Diethyl ether could be mixed with other anesthetic agents such as chloroform to make C. E. mixture, or chloroform and alcohol to make A. C. E. Mixture. In the 21st century, ether is used; the use of flammable ether was displaced by nonflammable fluorinated hydrocarbon anesthetics.
Halothane was the first such anesthetic developed and other used inhaled anesthetics, such as isoflurane and sevoflurane, are halogenated ethers. Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects. Prior to 2005 it was on the World Health Organization's List of Essential Medicines for use as an anesthetic. Ether was once used in pharmaceutical formulations. A mixture of alcohol and ether, one part of diethyl ether and three parts of ethanol, was known as "Spirit of ether", Hoffman's Anodyne or Hoffman's Drops. In the United States this concoction was removed from the Pharmacopeia at some point prior to June 1917, as a study published by William Procter, Jr. in the American Journal of Pharmacy as early as 1852 showed that there were differences in formulation to be found between commercial manufacturers, between international pharmacopoeia, from Hoffman's original recipe. The anesthetic and intoxicating effects of ether have made it a recreational drug.
Diethyl ether in anesthetic dosage is an inhalant which has a long history
Cobalt chloride is an inorganic compound of cobalt and chlorine, with the formula CoCl2. It is a sky blue crystalline solid; the compound forms several hydrates CoCl2•nH2O, for n = 1, 2, 6, 9. Claims of the formation of tri- and tetrahydrates have not been confirmed; the dihydrate is purple and hexahydrate is pink. It is supplied as the hexahydrate CoCl2·6H2O, one of the most used cobalt compounds in the lab; because of the ease of the hydration/dehydration reaction, the resulting color change, cobalt chloride is used as an indicator for water in desiccants. Niche uses of cobalt chloride include its role in organic synthesis and electroplating objects with cobalt metal. Cobalt chloride has been classified as a substance of high concern by the European Chemicals Agency as it is a suspected carcinogen. At room temperature, anhydrous cobalt chloride has the CdCl2 structure in which the cobalt ions are octahedrally coordinated. At about 706 C, the coordination is believed to change to tetrahedral; the vapor pressure has been reported as 7.6 mm Hg at the melting point.
Cobalt chloride is soluble in water. Under atmospheric pressure, the mass concentration of a saturated solution of CoCl2 in water is about 54% at the boiling point, 120.2 °C. Diluted aqueous solutions of CoCl2 contain the species 2+, besides chloride ions. Concentrated solutions are red at room temperature but become blue at higher temperatures; the crystal unit of the solid hexahydrate CoCl2•6H2O contains the neutral molecule trans-CoCl24 and two molecules of water of crystallization. This species dissolves in water and alcohol; the anhydrous salt is hygroscopic and the hexahydrate is deliquescent. Cobalt chloride can be prepared in aqueous solution from cobalt hydroxide or cobalt carbonate and hydrochloric acid: CoCO3 + 2 HCl → CoCl2 + CO2 Co2 + 2 HCl → CoCl2 + 2H2OThe solid dihydrate and hexahydrate can be obtained by evaporation. Cooling saturated aqueous solutions yields the dihydrate between 120.2 °C and 51.25 °C, the hexahydrate below 51.25 °C. Water ice, rather than cobalt chloride, will crystallize from solutions with concentration below 29%.
The monohydrate and the anhydrous forms can be obtained by cooling solutions only under high pressure, above 206 °C and 335 °C, respectively. The anhydrous compound can be prepared by heating the hydrates. On rapid heating or in a closed container, each of the 6-, 2-, 1- hydrates melts into a mixture of the next lower hydrate and a saturated solution -- at 51.25 °C, 206 °C, 335 °C, respectively. On slow heating in an open container, water evaporates out of each of the solid 6-, 2-, 1- hydrates, leaving the next lower hydrate -- at about 40 °C, 89 °C, 126 °C, respectively. Dehydration can be effected with trimethylsilyl chloride: CoCl2•6H2O + 12 3SiCl → CoCl2 + 62O + 12 HClThe anhydrous compound can be purified by sublimation in vacuum. In the laboratory, cobalt chloride serves as a common precursor to other cobalt compounds. Aqueous solutions of the salt behave like other cobalt salts since these solutions consist of the 2+ ion regardless of the anion. For example, such solutions give a precipitate of Cobalt sulfide CoS upon treatment with hydrogen sulfide H2S.
The hexahydrate and the anhydrous salt are weak Lewis acids. The adducts are either octahedral or tetrahedral. With pyridine, one obtains an octahedral complex: CoCl2·6H2O + 4 C5H5N → CoCl24 + 6 H2OWith triphenylphosphine, a tetrahedral complex results: CoCl2·6H2O + 2 P3 → CoCl22 + 6 H2OSalts of the anionic complex CoCl42− can be prepared using tetraethylammonium chloride: CoCl2 + 2 Cl → 2The 2− ion is the blue ion that forms upon addition of hydrochloric acid to aqueous solutions of hydrated cobalt chloride, which are pink. Reaction of the anhydrous compound with sodium cyclopentadienide gives cobaltocene Co2; this 19-electron species is a good reducing agent, being oxidised to the yellow 18-electron cobaltacenium cation +. Compounds of cobalt in the +3 oxidation state exist, such as cobalt fluoride CoF3, nitrate Co3, sulfate Co23. On the other hand, cobalt chlorides can be obtained if the cobalt is bound to other ligands of greater Lewis basicity than chloride, such as amines. For example, in the presence of ammonia, cobalt chloride is oxidised by atmospheric oxygen to hexamminecobalt chloride: 4 CoCl2·6H2O + 4 NH4Cl + 20 NH3 + O2 → 4 Cl3 + 26 H2OSimilar reactions occur with other amines.
These reactions are performed in the presence of charcoal as a catalyst, or with hydrogen peroxide H2O2 substituted for atmospheric oxygen. Other basic ligands, including carbonate and oxalate, induce the formation of Co derivatives. Simple carboxylates and halides do not. Unlike Co complexes, Co complexes are slow to exchange ligands, so they are said to be kinetically inert; the German chemist Alfred Werner was awarded the Nobel prize in 1913 for his studies on a series of these cobalt compounds, work that led to an understanding of the structures of such coordination compounds. Reaction of 1-norbonyllithium with the CoCl2·THF in pentane produces the brown, thermally stable cobalt tetralkyl — a rare example of a stable transition metal/saturated alkane compound, different products are obtained in other solvents. In 2005–06, cobalt chloride was the eighth-most-prevalent allergen in p
In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies between different classes of hydrates, some of which were so labeled before their chemical structure was understood. In organic chemistry, a hydrate is a compound formed by the addition of water or its elements to another molecule. For example: ethanol, CH3–CH2–OH, is the product of the hydration reaction of ethene, CH2=CH2, formed by the addition of H to one C and OH to the other C, so can be considered as the hydrate of ethene. A molecule of water may be eliminated, for example by the action of sulfuric acid. Another example is chloral hydrate, CCl3–CH2, which can be formed by reaction of water with chloral, CCl3–CH=O. Many organic molecules, as well as inorganic molecules, form crystals that incorporate water into the crystalline structure without chemical alteration of the organic molecule; the sugar trehalose, for example, exists as a dihydrate. Protein crystals have as much as 50% water content.
Molecules are labeled as hydrates for historical reasons not covered above. Glucose, C6H12O6, was thought of as C66 and described as a carbohydrate. Methanol is sold as "methyl hydrate", implying the incorrect formula CH3OH2, while the correct formula is CH3–OH. Hydrates are inorganic salts "containing water molecules combined in a definite ratio as an integral part of the crystal" that are either bound to a metal center or that have crystallized with the metal complex; such hydrates are said to contain water of crystallization or water of hydration. If the water is heavy water, where the hydrogen involved is the isotope deuterium the term deuterate may be used in place of hydrate. A colorful example is cobalt chloride, which turns from blue to red upon hydration, can therefore be used as a water indicator; the notation "hydrated compound⋅nH2O", where n is the number of water molecules per formula unit of the salt, is used to show that a salt is hydrated. The n is a low integer, though it is possible for fractional values to occur.
For example, in a monohydrate n is one, in a hexahydrate n is 6. Numerical prefixes of Greek origin are: A hydrate which has lost water is referred to as an anhydride. A substance that does not contain any water is referred to as anhydrous; some anhydrous compounds are hydrated so that they are said to be hygroscopic and are used as drying agents or desiccants. Clathrate hydrates are water ice with gas molecules trapped within. An important example is methane hydrate. Nonpolar molecules such as methane can form clathrate hydrates with water under high pressure. Although there is no hydrogen bonding between water and guest molecules when methane is the guest molecule of the clathrate, guest-host hydrogen bonding forms when the guest is a larger organic molecule such as tetrahydrofuran. In such cases the guest-host hydrogen bonds result in the formation of L-type Bjerrum defects in the clathrate lattice; the stability of hydrates is determined by the nature of the compounds, their temperature, the relative humidity
The density, or more the volumetric mass density, of a substance is its mass per unit volume. The symbol most used for density is ρ, although the Latin letter D can be used. Mathematically, density is defined as mass divided by volume: ρ = m V where ρ is the density, m is the mass, V is the volume. In some cases, density is loosely defined as its weight per unit volume, although this is scientifically inaccurate – this quantity is more called specific weight. For a pure substance the density has the same numerical value as its mass concentration. Different materials have different densities, density may be relevant to buoyancy and packaging. Osmium and iridium are the densest known elements at standard conditions for temperature and pressure but certain chemical compounds may be denser. To simplify comparisons of density across different systems of units, it is sometimes replaced by the dimensionless quantity "relative density" or "specific gravity", i.e. the ratio of the density of the material to that of a standard material water.
Thus a relative density less than one means. The density of a material varies with pressure; this variation is small for solids and liquids but much greater for gases. Increasing the pressure on an object decreases the volume of the object and thus increases its density. Increasing the temperature of a substance decreases its density by increasing its volume. In most materials, heating the bottom of a fluid results in convection of the heat from the bottom to the top, due to the decrease in the density of the heated fluid; this causes it to rise relative to more dense unheated material. The reciprocal of the density of a substance is called its specific volume, a term sometimes used in thermodynamics. Density is an intensive property in that increasing the amount of a substance does not increase its density. In a well-known but apocryphal tale, Archimedes was given the task of determining whether King Hiero's goldsmith was embezzling gold during the manufacture of a golden wreath dedicated to the gods and replacing it with another, cheaper alloy.
Archimedes knew that the irregularly shaped wreath could be crushed into a cube whose volume could be calculated and compared with the mass. Baffled, Archimedes is said to have taken an immersion bath and observed from the rise of the water upon entering that he could calculate the volume of the gold wreath through the displacement of the water. Upon this discovery, he leapt from his bath and ran naked through the streets shouting, "Eureka! Eureka!". As a result, the term "eureka" entered common parlance and is used today to indicate a moment of enlightenment; the story first appeared in written form in Vitruvius' books of architecture, two centuries after it took place. Some scholars have doubted the accuracy of this tale, saying among other things that the method would have required precise measurements that would have been difficult to make at the time. From the equation for density, mass density has units of mass divided by volume; as there are many units of mass and volume covering many different magnitudes there are a large number of units for mass density in use.
The SI unit of kilogram per cubic metre and the cgs unit of gram per cubic centimetre are the most used units for density. One g/cm3 is equal to one thousand kg/m3. One cubic centimetre is equal to one millilitre. In industry, other larger or smaller units of mass and or volume are more practical and US customary units may be used. See below for a list of some of the most common units of density. A number of techniques as well as standards exist for the measurement of density of materials; such techniques include the use of a hydrometer, Hydrostatic balance, immersed body method, air comparison pycnometer, oscillating densitometer, as well as pour and tap. However, each individual method or technique measures different types of density, therefore it is necessary to have an understanding of the type of density being measured as well as the type of material in question; the density at all points of a homogeneous object equals its total mass divided by its total volume. The mass is measured with a scale or balance.
To determine the density of a liquid or a gas, a hydrometer, a dasymeter or a Coriolis flow meter may be used, respectively. Hydrostatic weighing uses the displacement of water due to a submerged object to determine the density of the object. If the body is not homogeneous its density varies between different regions of the object. In that case the density around any given location is determined by calculating the density of a small volume around that location. In the limit of an infinitesimal volume the density of an inhomogeneous object at a point becomes: ρ = d m / d V, where d V is an elementary volume at position r; the mass of the body t
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.