It is one such subset of modern chemical nomenclature, that of polycyclic fused. The iupac nomemclature of polycyclic compounds jstage. Uci chem 125 advanced organic chemistry spring 2016 lec 2. Polycyclic alkanes there are four basic types of polycyclic systems based on how the rings are connected together. Weve done tons of iupac nomenclature for simple molecules, but once we start introducing multiple rings, things get trickier. However, many cyclic compounds have an element other than carbon atoms in the ring. If the rings are fused, the compounds are called bi, tri, tetra or polycyclic alkanes representing condensed and bridged systems as well as spiro compounds. According to iupac nomenclature of substituted aromatic compounds, the substituent name is placed as a prefix to the name of aromatic compounds. Similar compounds include chrysene, pyrene, benzoapyrene. By definition, polycyclic aromatic hydrocarbons have multiple cycles, precluding benzene from being considered a pah. A majority of these compounds, however, are referred to by singular names that are unique. If one of the substituents can be incorporated into a name, the name is used, and that incorporated substituent is given the 1position.
Aromatic compounds with only one group attached to the benzene ring. In a polycyclic compound, a ring orthofused to different sides of two other rings that are themselves ortho fused together i. Baeyer convention of nomenclature are briefly described below for bicyclic. The data supplied in this structure index comply with iupac rules for naming fused ring systems, detailed in the nomenclature of organic compounds 8 and.
So far we have studied only aromatic compounds with carboncontaining rings. The nomenclature of fusedring arenes and heterocycles. Although polycyclic compounds are important, they are highly complex and typically have common names accepted by iupac. Other authors consider pahs to start with the tricyclic species phenanthrene and. Gold book terms 127 from the chemical nomenclature and structure representation viii a. A few monosubstituted compounds are named by using a group name as a prefix to benzene, as shown by the combined names listed below. Short summary of iupac nomenclature of organic compounds introduction the purpose of the iupac system of nomenclature is to establish an international standard of naming compounds to facilitate communication. Generalized ane nomenclature is divided into carbane nomenclature, which covers the traditional substitutive nomenclature for carbon parent hydrides, and heterane nomenclature, which relates to atoms other than carbon, the heteroatoms in the nomenclature. The systems can be further classified according to the number of rings present e. Polycyclic aromatic hydrocarbons pahs formation in grilled meat productsanalysis and modeling with artificial neural networks. Polycyclic aromatic hydrocarbons pahs are a class of hazardous organic compounds consisting of three or more fused benzene rings in linear, angular, and cluster arrangements. The two simplest unsaturated compoundsethylene ethene and acetylene ethyne were once used as anesthetics and were introduced to the medical field in 1924. Clicking on the structures in the following table will lead to threedimensional representations of these compounds. Associated identifiers there is no information about former or incorrectly used identifiers.
When the name of a component in a fusion name contains locants numerals or letters that do not apply. Compounds from fused benzene or aromatic heterocyclic rings are themselves aromatic naphthalene. Iupac names for spiro alkanes have the format spiroa. In replacement nomenclature, the heterocycles name is composed of the carbocycles name and a prefix that denotes the heteroatom. There are three systems for naming heterocyclic compounds. The nomenclature of compounds of this type is beyond the scope of this course. Guidance for facilities reporting chemicals from the polycyclic aromatic compounds category under epcra section 3. Overview of polycyclic aromatic compounds pac article pdf available in polycyclic aromatic compounds 3524 march 2015 with 1,5 reads how we measure reads.
The alkanes are classified as continuous chain that is, unbranched if all the carbon atoms in the chain are linked to no more than two other car. Count the total number of carbons across the entire molecule. An aromatic compound is any compound that contains a benzene ring or has certain benzenelike properties. Polycyclic aromatic compounds pacs can have multiple sources in the athabasca oil sands region aosr. Where possible, cas numbers aresupplied tofacilitateliterature searches. The current study was designed to identify and explore the potential of nitrogen heterocyclic pacs npacs as source indicators in snowpack, lake sediment and passive air samples from the aosr during 20142015. The main ring is shown in bold in examples for vb2 to vb4. The pentacyclic compound iii was called dinaphthanthracene.
Can use o, p, m, or numbers when naming disubstitued aromatic rings. Aromatic compounds definition, example, properties. Recent advances on diversity oriented heterocycle synthesis of fused quinolines and its biological evaluation. This tells you the alkane parent name that goes at the end. To advance source identification of ctscderived pacs, we use comprehensive two. Hydrocarbon nomenclature of alkenes and alkynes britannica. However, efforts to assess the environmental fate and impacts of ctscderived pacs are hindered by the ubiquity of routinely monitored pacs released from other environmental sources.
Nomenclature of polycyclic aromatic compounds chapter 19. These compounds, called heterocyclic compounds, are discussed in chapter 15 organic acids and bases and some of their derivatives, section 15. If the benzene ring has more than two substituents, the substituents are numbered. Nomenclature of cycloalkanes mcc organic chemistry. You may need a pdf reader to view some of the files on this page. The aromatic heterocycles have been grouped into those with six.
Nomenclature of polycyclic hydrocarbons springerlink. Chapter 2, sect 2024 september, 2004 iupac provisional. The goal of the system is to give each structure a unique and unambiguous name, and to correlate each name with a unique and unambiguous. The components are named according to rules a21, b1 and b2. The replacement nomenclature thus, aza, oxa, and thia are prefixes for a nitrogen ring atom, an oxygen ring atom, and a sulfur ring atom, respectively. Hydrocarbon hydrocarbon nomenclature of alkenes and alkynes. Nomenclature, structure, properties nomenclature and structure.
However, the common names do not generally follow the basic iupac nomenclature rules. Benzene ring numbering system cyclic compound original numbering polycyclic. The nomenclature of substituted benzene ring compounds is less systematic than that of the alkanes, alkenes and alkynes. Includes only the 21 chemicals listed as components of this polycyclic aromatic compounds category, to be reported as the category and not as individual chemical substances. Count the number of carbons to the left, and to the right of your spirocarbon center. However, when naming bicyclic compounds, you must start at the bridgehead and move toward the largest ring. Bicyclic ring systems a bridged bicycloalkane is a bicycloalkane whose molecule has two carbon atoms shared by all three rings identifiable in the molecule.
Source samples including petroleum coke petcoke, haul road dust, and. Higher alkenes and alkynes are named by counting the number of carbons in the longest continuous chain that includes the double or triple bond and appending an ene alkene or yne alkyne suffix to the stem name of the. Alkanes can be joined at the ends to make ring compounds. The two simplest unsaturated compounds ethylene ethene and acetylene ethyne were once used as anesthetics and were introduced to the medical field in 1924. Compounds were not arbitrarily drawn and named simply to enumerate all possibleisomers. Characterization of polycyclic aromatic compounds in. This usually originates from the compounds occurrence, its. Short summary of iupac nomenclature of organic compounds. For example, a benzene ring attached to a onenitro group is named as nitrobenzene.
Includes emission factors and examples of mixtures. Naphthalene, with its two rings, is considered the simplest polycyclic aromatic hydrocarbon by us epa and cdc for policy contexts. There are slight differences in the way in which they are named. The international union of applied and pure chemistry iupac has issued rules and recommendations on chemical nomenclature including organic compounds like pah since 1957. A fused aromaticring compound consisting only of carbon and hydrogen. If we were naming nonbicyclic compounds, you definitely would want the lowest number on each substituent. Ethylene and acetylene are synonyms in the iupac nomenclature system for ethene and ethyne, respectively.
The nomenclature of polycyclic aromatic hydrocarbons pah and their derivatives has undergone substantial changes since the beginning of the 20th century. If two rings share two or more common atoms, the compound is called a bicyclic compound. Heterocyclic nomenclature a selection of the structures, names and standard numbering of the more common heteroaromatic systems and some common non aromatic heterocycles are given here as a necessary prelude to the discussions which follow in subsequent chapters. Coal tarbased sealcoat ctsc products are an urban source of polycyclic aromatic compounds pacs to the environment.
831 522 301 443 347 969 1321 662 24 755 524 844 1428 349 1396 562 1193 1397 1457 323 875 1181 242 1396 491 684 641 1009 1000 1070 235 1275 1213 407 1445 38 1272 541 488 875 1336 1317 104 821 806 366 213