1.
X-ray crystallography
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By measuring the angles and intensities of these diffracted beams, a crystallographer can produce a three-dimensional picture of the density of electrons within the crystal. From this electron density, the positions of the atoms in the crystal can be determined, as well as their chemical bonds, their disorder. The method also revealed the structure and function of biological molecules, including vitamins, drugs, proteins. X-ray crystallography is still the method for characterizing the atomic structure of new materials. In a single-crystal X-ray diffraction measurement, a crystal is mounted on a goniometer, the goniometer is used to position the crystal at selected orientations. The crystal is illuminated with a finely focused monochromatic beam of X-rays, poor resolution or even errors may result if the crystals are too small, or not uniform enough in their internal makeup. X-ray crystallography is related to other methods for determining atomic structures. Similar diffraction patterns can be produced by scattering electrons or neutrons, for all above mentioned X-ray diffraction methods, the scattering is elastic, the scattered X-rays have the same wavelength as the incoming X-ray. By contrast, inelastic X-ray scattering methods are useful in studying excitations of the sample, Crystals, though long admired for their regularity and symmetry, were not investigated scientifically until the 17th century. Johannes Kepler hypothesized in his work Strena seu de Nive Sexangula that the symmetry of snowflake crystals was due to a regular packing of spherical water particles. The Danish scientist Nicolas Steno pioneered experimental investigations of crystal symmetry, hence, William Hallowes Miller in 1839 was able to give each face a unique label of three small integers, the Miller indices which remain in use today for identifying crystal faces. In the 19th century, a catalog of the possible symmetries of a crystal was worked out by Johan Hessel, Auguste Bravais, Evgraf Fedorov, Arthur Schönflies. Wilhelm Röntgen discovered X-rays in 1895, just as the studies of crystal symmetry were being concluded, physicists were initially uncertain of the nature of X-rays, but soon suspected that they were waves of electromagnetic radiation, in other words, another form of light. Single-slit experiments in the laboratory of Arnold Sommerfeld suggested that X-rays had a wavelength of about 1 angstrom, however, X-rays are composed of photons, and thus are not only waves of electromagnetic radiation but also exhibit particle-like properties. Albert Einstein introduced the concept in 1905, but it was not broadly accepted until 1922. Therefore, these properties of X-rays, such as their ionization of gases. Nevertheless, Braggs view was not broadly accepted and the observation of X-ray diffraction by Max von Laue in 1912 confirmed for most scientists that X-rays were a form of electromagnetic radiation, Crystals are regular arrays of atoms, and X-rays can be considered waves of electromagnetic radiation. Atoms scatter X-ray waves, primarily through the atoms electrons and this phenomenon is known as elastic scattering, and the electron is known as the scatterer
2.
Jmol
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Jmol is computer software for molecular modelling chemical structures in 3-dimensions. Jmol returns a 3D representation of a molecule that may be used as a teaching tool and it is written in the programming language Java, so it can run on the operating systems Windows, macOS, Linux, and Unix, if Java is installed. It is free and open-source software released under a GNU Lesser General Public License version 2.0, a standalone application and a software development kit exist that can be integrated into other Java applications, such as Bioclipse and Taverna. A popular feature is an applet that can be integrated into web pages to display molecules in a variety of ways, for example, molecules can be displayed as ball-and-stick models, space-filling models, ribbon diagrams, etc. Jmol supports a range of chemical file formats, including Protein Data Bank, Crystallographic Information File, MDL Molfile. There is also a JavaScript-only version, JSmol, that can be used on computers with no Java, the Jmol applet, among other abilities, offers an alternative to the Chime plug-in, which is no longer under active development. While Jmol has many features that Chime lacks, it does not claim to reproduce all Chime functions, most notably, Chime requires plug-in installation and Internet Explorer 6.0 or Firefox 2.0 on Microsoft Windows, or Netscape Communicator 4.8 on Mac OS9. Jmol requires Java installation and operates on a variety of platforms. For example, Jmol is fully functional in Mozilla Firefox, Internet Explorer, Opera, Google Chrome, fast and Scriptable Molecular Graphics in Web Browsers without Java3D
3.
Hydrocarbon
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In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon, and thus are group 14 hydrides. Hydrocarbons from which one atom has been removed are functional groups. Aromatic hydrocarbons, alkanes, alkenes, cycloalkanes and alkyne-based compounds are different types of hydrocarbons, the classifications for hydrocarbons, defined by IUPAC nomenclature of organic chemistry are as follows, Saturated hydrocarbons are the simplest of the hydrocarbon species. They are composed entirely of single bonds and are saturated with hydrogen, the formula for acyclic saturated hydrocarbons is CnH2n+2. The most general form of saturated hydrocarbons is CnH2n+2, where r is the number of rings and those with exactly one ring are the cycloalkanes. Saturated hydrocarbons are the basis of petroleum fuels and are found as linear or branched species. Substitution reaction is their characteristics property, hydrocarbons with the same molecular formula but different structural formulae are called structural isomers. As given in the example of 3-methylhexane and its higher homologues, chiral saturated hydrocarbons constitute the side chains of biomolecules such as chlorophyll and tocopherol. Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms and those with double bond are called alkenes. Those with one double bond have the formula CnH2n and those containing triple bonds are called alkyne. Those with one triple bond have the formula CnH2n−2, aromatic hydrocarbons, also known as arenes, are hydrocarbons that have at least one aromatic ring. Hydrocarbons can be gases, liquids, waxes or low melting solids or polymers, in terms of shells, carbon consists of an incomplete outer shell, which comprises 4 electrons, and thus has 4 electrons available for covalent or dative bonding. Some hydrocarbons also are abundant in the solar system, lakes of liquid methane and ethane have been found on Titan, Saturns largest moon, confirmed by the Cassini-Huygens Mission. Hydrocarbons are also abundant in nebulae forming polycyclic aromatic hydrocarbon compounds, hydrocarbons are a primary energy source for current civilizations. The predominant use of hydrocarbons is as a fuel source. In their solid form, hydrocarbons take the form of asphalt, mixtures of volatile hydrocarbons are now used in preference to the chlorofluorocarbons as a propellant for aerosol sprays, due to chlorofluorocarbons impact on the ozone layer. Methane and ethane are gaseous at ambient temperatures and cannot be liquefied by pressure alone. Propane is however easily liquefied, and exists in propane bottles mostly as a liquid, butane is so easily liquefied that it provides a safe, volatile fuel for small pocket lighters
4.
Benzene
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Benzene is an important organic chemical compound with the chemical formula C6H6. The benzene molecule is composed of 6 carbon atoms joined in a ring with 1 hydrogen atom attached to each, because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a constituent of crude oil and is one of the elementary petrochemicals. Because of the cyclic continuous pi bond between the atoms, benzene is classed as an aromatic hydrocarbon, the second -annulene. Benzene is a colorless and highly flammable liquid with a sweet smell and it is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced. Because benzene has a high number, it is an important component of gasoline. Because benzene is a carcinogen, most non-industrial applications have been limited. The word benzene derives historically from gum benzoin, a resin known to European pharmacists. An acidic material was derived from benzoin by sublimation, and named flowers of benzoin, the hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene. Michael Faraday first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, in 1833, Eilhard Mitscherlich produced it by distilling benzoic acid and lime. He gave the compound the name benzin, in 1845, Charles Mansfield, working under August Wilhelm von Hofmann, isolated benzene from coal tar. Four years later, Mansfield began the first industrial-scale production of benzene, gradually, the sense developed among chemists that a number of substances were chemically related to benzene, comprising a diverse chemical family. In 1855, Hofmann used the word aromatic to designate this family relationship, in 1997, benzene was detected in deep space. The empirical formula for benzene was known, but its highly polyunsaturated structure. In 1865, the German chemist Friedrich August Kekulé published a paper in French suggesting that the structure contained a ring of six carbon atoms with alternating single and double bonds, the next year he published a much longer paper in German on the same subject. Kekulés symmetrical ring could explain these facts, as well as benzenes 1,1 carbon-hydrogen ratio. Here Kekulé spoke of the creation of the theory and he said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake seizing its own tail. This vision, he said, came to him years of studying the nature of carbon-carbon bonds
5.
Proton nuclear magnetic resonance
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In samples where natural hydrogen is used, practically all the hydrogen consists of the isotope 1H. A full 1H atom is called protium, simple NMR spectra are recorded in solution, and solvent protons must not be allowed to interfere. However, a solvent without hydrogen, such as carbon tetrachloride, CCl4 or carbon disulphide, CS2, historically, deuterated solvents were supplied with a small amount of tetramethylsilane as an internal standard for calibrating the chemical shifts of each analyte proton. TMS is a molecule, with all protons being chemically equivalent, giving one single signal. It is volatile, making sample recovery easy as well, modern spectrometers are able to reference spectra based on the residual proton in the solvent. Deuterated solvents are now commonly supplied without TMS, deuterated solvents permit the use of deuterium frequency-field lock to offset the effect of the natural drift of the NMRs magnetic field B0. In order to provide deuterium lock, the NMR constantly monitors the deuterium signal resonance frequency from the solvent and makes changes to the B0 to keep the resonance frequency constant. Additionally, the signal may be used to accurately define 0 ppm as the resonant frequency of the lock solvent. Proton NMR spectra of most organic compounds are characterized by chemical shifts in the range +14 to -4 ppm, the integration curve for each proton reflects the abundance of the individual protons. The spectrum of ethyl chloride consists of a triplet at 1.5 ppm, the spectrum of benzene consists of a single peak at 7.2 ppm due to the diamagnetic ring current. Together with Carbon-13 NMR, proton NMR is a tool for molecular structure characterization. Chemical shift values, symbolized by δ, are not precise, deviations are in ±0.2 ppm range, sometimes more. The exact value of chemical shift depends on structure and the solvent, temperature, magnetic field in which the spectrum is being recorded. Hydrogen nuclei are sensitive to the hybridization of the atom to which the atom is attached. Nuclei tend to be deshielded by groups which withdraw electron density, deshielded nuclei resonate at higher δ values, whereas shielded nuclei resonate at lower δ values. Examples of electron withdrawing substituents are -OH, -OCOR, -OR, -NO2 and these cause a downfield shift of approximately 2–4 ppm for H atoms on Cα and of less than 1–2 ppm for H atoms on Cβ. Cα is an aliphatic C atom directly bonded to the substituent in question, carbonyl groups, olefinic fragments and aromatic rings contribute sp2 hybridized carbon atoms to an aliphatic chain. This causes a shift of 1–2 ppm at Cα
6.
Journal of the American Chemical Society
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The Journal of the American Chemical Society is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the Journal of Analytical and Applied Chemistry and the American Chemical Journal and it publishes original research papers in all fields of chemistry. Since 2002, the journal is edited by Peter J. Stang, in 2014, the journal moved to a hybrid open access publishing model. The Journal of the American Chemical Society is abstracted and indexed in Chemical Abstracts Service, Scopus, EBSCOhost, Thomson-Gale, ProQuest, PubMed, Web of Science, and SwetsWise. According to the Journal Citation Reports, it had a factor of 12.113 for 2014
7.
Aromatic hydrocarbon
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An aromatic hydrocarbon or arene is a hydrocarbon with sigma bonds and delocalized pi electrons between carbon atoms forming a circle. In contrast, aliphatic hydrocarbons lack this delocalization, the term aromatic was assigned before the physical mechanism determining aromaticity was discovered, the term was coined as such simply because many of the compounds have a sweet or pleasant odour. The configuration of six carbon atoms in compounds is known as a benzene ring, after the simplest possible such hydrocarbon. Aromatic hydrocarbons can be monocyclic or polycyclic, some non-benzene-based compounds called heteroarenes, which follow Hückels rule, are also called aromatic compounds. In these compounds, at least one atom is replaced by one of the heteroatoms oxygen, nitrogen. Benzene, C6H6, is the simplest aromatic hydrocarbon, and it was the first one named as such, the nature of its bonding was first recognized by August Kekulé in the 19th century. Each carbon atom in the cycle has four electrons to share. One goes to the atom, and one each to the two neighbouring carbons. The structure is alternatively illustrated as a circle around the inside of the ring to show six electrons floating around in delocalized molecular orbitals the size of the ring itself. This depiction represents the equivalent nature of the six carbon–carbon bonds all of bond order 1.5, the electrons are visualized as floating above and below the ring with the electromagnetic fields they generate acting to keep the ring flat. The proper use of the symbol is debated, it is used to describe any cyclic π system in some publications, jensen argues that, in line with Robinsons original proposal, the use of the circle symbol should be limited to monocyclic 6 π-electron systems. In this way the symbol for a six-center six-electron bond can be compared to the Y symbol for a three-center two-electron bond. A reaction that forms a compound from an unsaturated or partially unsaturated cyclic precursor is simply called an aromatization. Many laboratory methods exist for the synthesis of arenes from non-arene precursors. Many methods rely on cycloaddition reactions, alkyne trimerization describes the cyclization of three alkynes, in the Dötz reaction an alkyne, carbon monoxide and a chromium carbene complex are the reactants. Diels–Alder reactions of alkynes with pyrone or cyclopentadienone with expulsion of carbon dioxide or carbon monoxide also form arene compounds, in Bergman cyclization the reactants are an enyne plus a hydrogen donor. Arenes are reactants in many organic reactions, in aromatic substitution one substituent on the arene ring, usually hydrogen, is replaced by another substituent. The two main types are electrophilic aromatic substitution when the reagent is an electrophile and nucleophilic aromatic substitution when the reagent is a nucleophile
8.
Double bond
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A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that is two carbon atoms, can be found in alkenes. Many types of double bonds exist between two different elements, for example, in a carbonyl group with a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds, imines and sulfoxides, in skeletal formula the double bond is drawn as two parallel lines between the two connected atoms, typographically, the equals sign is used for this. Double bonds were first introduced in chemical notation by prominent Russian chemist Alexander Butlerov, double bonds involving carbon are stronger than single bonds and are also shorter. Double bonds are also electron-rich, which makes them reactive, the type of bonding can be explained in terms of orbital hybridization. In ethylene each carbon atom has three sp2 orbitals and one p-orbital, the three sp2 orbitals lie in a plane with ~120° angles. The p-orbital is perpendicular to this plane, when the carbon atoms approach each other, two of the sp2 orbitals overlap to form a sigma bond. At the same time, the two p-orbitals approach and together form a pi-bond. For maximum overlap, the p-orbitals have to parallel, and, therefore. This property gives rise to cis-trans isomerism, double bonds are shorter than single bonds because p-orbital overlap is maximized. With 133 pm, the ethylene C=C bond length is shorter than the C−C length in ethane with 154 pm. The double bond is stronger,636 kJ mol−1 versus 368 kJ mol−1. In an alternative representation, the double bond results from two overlapping sp3 orbitals as in a bent bond, in molecules, with alternating double bonds and single bonds, p-orbital overlap can exist over multiple atoms in a chain, giving rise to a conjugated system. Conjugation can be found in such as dienes and enones. In cyclic molecules, conjugation can lead to aromaticity, in cumulenes, two double bonds are adjacent. Double bonds are common for period 2 elements carbon, nitrogen, and oxygen, metals, too, can engage in multiple bonding in a metal ligand multiple bond. Double bonded compounds, alkene homologs, R2E=ER2 are now known for all of the heavier group 14 elements, unlike the alkenes these compounds are not planar but adopt twisted and/or trans bent structures
9.
Homoaromaticity
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Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is interrupted by a single sp3 hybridized carbon atom. This formal discontinuity is apparently bridged by p-orbital overlap, maintaining a cycle of π electrons that is responsible for this preserved chemical stability. The concept of homoaromaticity was pioneered by Saul Winstein in 1959, to date, homoaromatic compounds are known to exist as cationic and anionic species, and some studies support the existence of neutral homoaromatic molecules, though these are less common. The homotropylium cation is perhaps the best studied example of a homoaromatic compound, the term homoaromaticity derives from the structural similarity between homoaromatic compounds and the analogous homo-conjugated alkenes previously observed in the literature. The IUPAC Gold Book requires that Bis-, Tris-, etc. prefixes be used to describe compounds in which two, three, etc. sp3 centers separately interrupt conjugation of the aromatic system. The concept of homoaromaticity has its origins in the debate over the non-classical carbonium ions that occurred in the 1950s, Saul Winstein, a famous proponent of the non-classical ion model, first described homoaromaticity while studying the 3-bicyclohexyl cation. In a series of experiments, Winstein et al. observed that the solvolysis reaction occurred empirically faster when the tosyl leaving group was in the equatorial position. The group ascribed this difference in rates to the anchimeric assistance invoked by the cis isomer. This result thus supported a non-classical structure for the cation, Winstein subsequently observed that this non-classical model of the 3-bicyclohexyl cation is analogous to the previously well-studied aromatic cyclopropenyl cation. Like the cyclopropenyl cation, positive charge is delocalized over three equivalent carbons containing two π electrons and this electronic configuration thus satisfies Huckels rule for aromaticity. The group thus proposed the name tris-homocyclopropenyl—the tris-homo counterpart to the cyclopropenyl cation, the criterion for aromaticity has evolved as new developments and inisights continue to contribute to our understanding of these remarkably stable organic molecules. The required characteristics of these molecules has remained the subject of some controversy. Classically, aromatic compounds were defined as planar molecules that possess a cyclically delocalized system of π electrons, most importantly, these conjugated ring systems are known to exhibit enormous thermochemical stability relative to predictions based on localized resonance structures. Consequently, the criterion for homoaromatic delocalization remains similarly ambiguous and somewhat controversial, after initial reports of a homoaromatic structure for the tris-homocyclopropenyl cation were published by Winstein, many groups began to report observations of similar compounds. Much of the evidence for homoaromaticity comes from observations of unusual NMR properties associated with this molecule. From this observation, Pettit, et al. concluded that the structure of the cyclooctatrienyl cation must be incorrect. Upon further consideration, Pettit was inclined to represent the compound as the homotropylium ion and this structure shows how delocalization is cyclic and involves 6 π electrons, consistent with Huckels rule for aromaticity. The magnetic field of the NMR could thus induce a current in the ion
10.
Aromaticity
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Aromatic molecules are very stable, and do not break apart easily to react with other substances. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, since the most common aromatic compounds are derivatives of benzene, the word “aromatic” occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many aromatic compounds exist. In living organisms, for example, the most common aromatic rings are the bases in RNA and DNA. An aromatic functional group or other substituent is called an aryl group, the earliest use of the term aromatic was in an article by August Wilhelm Hofmann in 1855. Hofmann used the term for a class of compounds, many of which have odors. In terms of the nature of the molecule, aromaticity describes a conjugated system often made of alternating single and double bonds in a ring. This configuration allows for the electrons in the pi system to be delocalized around the ring, increasing the molecules stability. The molecule cannot be represented by one structure, but rather a hybrid of different structures. These molecules cannot be found in one of these representations, with the longer single bonds in one location. Rather, the molecule exhibits bond lengths in between those of single and double bonds and this commonly seen model of aromatic rings, namely the idea that benzene was formed from a six-membered carbon ring with alternating single and double bonds, was developed by August Kekulé. The model for benzene consists of two forms, which corresponds to the double and single bonds superimposing to produce six one-and-a-half bonds. Benzene is a stable molecule than would be expected without accounting for charge delocalization. As is standard for resonance diagrams, the use of an arrow indicates that two structures are not distinct entities but merely hypothetical possibilities. Neither is a representation of the actual compound, which is best represented by a hybrid of these structures. A C=C bond is shorter than a C−C bond, but benzene is perfectly hexagonal—all six carbon–carbon bonds have the same length, intermediate between that of a single and that of a double bond. In a cyclic molecule with three alternating double bonds, cyclohexatriene, the length of the single bond would be 1.54 Å. However, in a molecule of benzene, the length of each of the bonds is 1.40 Å, a better representation is that of the circular π-bond, in which the electron density is evenly distributed through a π-bond above and below the ring
11.
Resonance (chemistry)
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In chemistry, resonance or mesomerism is a way of describing delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by one single Lewis structure. A molecule or ion with such delocalized electrons is represented by several contributing structures, each contributing structure can be represented by a Lewis structure, with only an integer number of covalent bonds between each pair of atoms within the structure. Several Lewis structures are used collectively to describe the molecular structure. Electron delocalization lowers the energy of the substance and thus makes it more stable than any of the contributing structures. The difference between the energy of the actual structure and that of the contributing structure with the lowest potential energy is called the resonance energy or delocalization energy. An isomer is a molecule with the chemical formula but with different arrangements of atoms in space. Resonance contributors of a molecule, on the contrary, can differ by the arrangements of electrons. Therefore, the resonance hybrid cannot be represented by a combination of isomers, benzene undergoes substitution reactions, rather than addition reactions as typical for alkenes. He proposed that the bond in benzene is intermediate of a single and double bond. The mechanism of resonance was introduced into quantum mechanics by Werner Heisenberg in 1926 in a discussion of the states of the helium atom. He compared the structure of the atom with the classical system of resonating coupled harmonic oscillators. Linus Pauling used this mechanism to explain the partial valence of molecules in 1928, the alternative term mesomerism popular in German and French publications with the same meaning was introduced by C. K. Ingold in 1938, but did not catch on in the English literature. The current concept of effect has taken on a related. The double headed arrow was introduced by the German chemist Fritz Arndt who preferred the German phrase zwischenstufe or intermediate stage, the real structure is an intermediate of these structures represented by a resonance hybrid. The contributing structures are not isomers and they differ only in the position of electrons, not in the position of nuclei. Each Lewis formula must have the number of valence electrons. Bonds that have different bond orders in different contributing structures do not have typical bond lengths, the real structure has a lower total potential energy than each of the contributing structures would have. This means that it is more stable than each separate contributing structure would be and it is a common misconception that resonance structures are actual transient states of the molecule, with the molecule oscillating between them or existing as an equilibrium between them
12.
Simplified molecular-input line-entry system
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The simplified molecular-input line-entry system is a specification in 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 modified and extended. In 2007, a standard called OpenSMILES was developed in the open-source chemistry community. Other linear notations include the Wiswesser Line Notation, ROSDAL and SLN, the original SMILES specification was initiated by David Weininger at the USEPA Mid-Continent Ecology Division Laboratory in Duluth in the 1980s. The Environmental Protection Agency funded the project to develop SMILES. It has since modified and extended by others, most notably by Daylight Chemical Information Systems. In 2007, a 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 generally considered to have the advantage of being slightly more human-readable than InChI, the term SMILES refers to a line notation for encoding molecular structures and specific instances should strictly be called SMILES strings. However, the term SMILES is also used to refer to both a single SMILES string and a number of SMILES strings, the exact meaning is usually apparent from the context. The terms canonical and isomeric can lead to confusion when applied to SMILES. The terms describe different attributes of SMILES strings and are not mutually exclusive, typically, a number of equally 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, of the many possible strings, these algorithms choose only one of them. This SMILES is unique for each structure, although dependent on the algorithm used to generate it. These algorithms first convert the SMILES to a representation of the molecular structure. A common application of canonical SMILES is indexing and ensuring uniqueness of molecules in a database, there is currently 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, and these are structural features that cannot be specified by connectivity alone and SMILES which encode this information are termed isomeric SMILES
