Danh pháp IUPAC complete

TABLE OF CONTENTS en da tio ns i CHAPTER P-1 NOMENCLATURE OF ORGANIC COMPOUNDS Introduction Scope of nomenclature of organic compounds Preferred, preselected and retained names Operations in nomenclature General rules Types of nomenclature Name writing Introduction Mononuclear and polynuclear acyclic parent hydrides Monocyclic hydrides Polyalicyclic (von Baeyer) systems Spiro compounds Fused and bridged fused systems Phane nomenclature Fullerenes Ring assemblies Prefixes denoting substituent groups derived from parent hydrides vis ion al Re P-20 P-21 P-22 P-23 P-24 P-25 P-26 P-27 P-28 P-29 PARENT HYDRIDES co CHAPTER P-2 m m P-10 P-11 P-12 P-13 P-14 P-15 P-16 CHAPTER P-3 CHARACTERISTIC (FUNCTIONAL) GROUPS PA C P-33 P-34 P-35 Introduction Modification of the degree of hydrogenation of parent hydrides Prefixes for substituent groups derived from parent hydrides with a modified degree of hydrogenation Suffixes Parent structures other than parent hydrides and corresponding prefixes for substituent groups Prefixes denoting characteristic groups Pr o P-30 P-31 P-32 CHAPTER P-4 RULES FOR NAME CONSTRUCTION IU P-40 P-41 P-42 Page of 1306 Introduction Seniority order of classes Seniority order of acids DRAFT October 2004 ii Seniority order of suffixes Seniority order of parent structures The principal chain in substituent groups Substitution rules for parent structures with retained names en da tio ns P-43 P-44 P-45 P-46 CHAPTER P-5 CONSTRUCTING PREFERRED IUPAC NAMES P-50 P-51 P-52 Introduction Selecting the preferred type of nomenclature Selecting preferred IUPAC names and preselected names (see P-12) for parent hydrides names Selecting the preferred method for modifying the degree of hydrogenation for parent hydrides Selecting the preferred suffix (principal group) Selecting preferred retained names Selecting preferred substituent group names Selecting preferred names for tautomeric compounds Name construction P-53 co m m P-54 P-55 P-56 P-57 P-58 Re CHAPTER P-6 APPLICATIONS TO SPECIFIC CLASSES OF COMPOUNDS Introduction Substitutive nomenclature: prefix mode Amines and imines Hydroxy compounds, ethers, peroxols, peroxides and chalcogen analogues Ketones , pseudo ketones and heterones, and chalcogen analogues Acids and derivatives Amides, hydrazides, nitriles, aldehydes Oxoacids used as parents for organic compounds Nomenclature of other classes of compounds Organometallic compounds vis ion al P-60 P-61 P-62 P-63 P-64 P-65 P-66 P-67 P-68 P-69 General methodology Radicals Anions Cations Zwitterions Radicals ions Delocalized radicals and ions Preferred names IU PA C P-70 P-71 P-72 P-73 P-74 P-75 P-76 P-77 Pr o CHAPTER P-7 RADICALS, IONS, AND RELATED SPECIES DRAFT October 2004 Page of 1306 iii en da tio ns CHAPTER P-8 ISOTOPICALLY MODIFIED COMPOUNDS P-80 P-81 P-82 P-83 P-84 Introduction Symbols and definitions Isotopically substituted compounds Isotopically labelled compounds Comparative examples of formulae and names of isotopically modified compounds m CHAPTER P-9 SPECIFICATION OF CONFIGURATION AND CONFORMATION Introduction CIP Priority and sequence rules Configurational stereodescriptors Applications of stereodescriptors Conformation and conformational stereodescriptors co m P-90 P-91 P-92 P-93 P-94 Re CHAPTER P-10 PARENT STRUCTURES FOR NATURAL PRODUCTS AND RELATED COMPOUNDS Introduction Nomenclature for natural products based on parent hydrides (alkaloids, steroids, terpenes, carotenes, corrinoids, tetrapyrroles, and similar compounds) Carbohydrate nomenclature Amino acids and peptides Cyclitols Nucleosides Nucleotides Lipids ion al P-100 P-101 Pr o vis P-102 P-103 P-104 P-105 P-106 P-107 Appendix Seniority list of elements and ‘a’ terms used in replacement (‘a’) nomenclature in decreasing order of seniority IU PA C Appendix Usual detachable prefixes used in substitutive nomenclature Page of 1306 DRAFT October 2004 Preferred IUPAC names List of tables, September , 2004 iv Chapter 1.4 1.5 1.6 General rules Elements included in these recommendations, page Nomenclature operations, page Standard bonding numbers for the elements of Groups 13, 14, 15, 16, and 17, page 24 Basic numerical terms (multiplying prefixes), page 25 Skeletal replacement ‘a’ prefixes, page 64 Prefixes and infixes in functional replacement nomenclature, page 71 Chapter m 1.1 1.2 1.3 en da tio ns LIST OF TABLES Parent hydrides Systematic names of mononuclear hydrides of Groups 13, 14, 15, 16, and 17 with normal bonding numbers, page 2.2 Retained names of mancude heteromonocyclic parent hydrides, page 11 2.3 Retained names of saturated heteromonocyclic parent hydrides used as preferred names and in general nomenclature, page 12 2.4 Hantzsch-Widman system prefixes (in decreasing order of seniority), page 13 2.5 Hantzsch-Widman system stems, page 14 2.6 Retained names for von Baeyer parent hydrides, page 41 2.7 Retained names of hydrocarbon parent components in descending order of seniority, page 75 2.8 Retained names of heterocyclic parent components in descending order of seniority, page 81 2.9 Names for nitrogeneous parent components modified by by P and As replacement page 84 2.10 Retained names for substituent groups derived from parent hydrides, page 227 vis ion al Re co m 2.1 Chapter 3.3 PA C 3.4 Retained names of partially saturated heteromonocyclic parent hydrides, page 21 Retained names of prefixes for partially saturated polycyclic parent hydrides, page 33 Basic suffixes, in decreasing order of seniority for citation as the principal characteristic group, page 35 Affixes for radical and ionic centers in parent structures, page 38 Pr o 3.1 3.2 Characteristic (functional) groups Chapter IU 4.1 4.2 Rules for name construction General compound classes listed in decreasing order of seniority for choosing and naming the principal class (radicals and ions) or characteristic group in an organic compound, page Prefixes and infixes, in decreasing order of seniority, used to generate suffixes in preferred IUPAC names by functional replacement, page DRAFT October 2004 Page of 1306 Preferred IUPAC names List of tables, September , 2004 4.4 Carboxylic and sulfonic acids suffixes generated for IUPAC preferred names by functional replacement, in decreasing order of seniority, page Complete list of suffixes and functional replacement analogues for IUPAC preferred names, in decreasing order of seniority, page 12 Chapter Constructing preferred IUPAC names 5.1 5.2 Retained heteromonocyclic names modified by ‘hydro’ prefixes, page 20 Characteristic groups always cited as prefixes in substitutive nomenclature, page 53 Chapter Application to specific classes of compounds m m Re Retained names of mononuclear parent cations of Groups 15, 16 and 17, page 33 Suffixes for cationic characteristic groups, page 35 Retained names used as preferred names and in general nomenclature, page 80 Preferred IUPAC names for radicals and ions derived from functionalized and functional parents, page 88 al 7.1 7.2 7.3 7.4 Radical and ions, and related species co Chapter Chapter 8.1 Isotopically modified compounds Comparative examples of Formulas and names of isotopically modified compounds, page 18 Chapter 10 10.3 List of recommended names of stereoparent structures, page Retained names (with recommended three-letter abbreviations in parentheses) and structures (in the aldehydic acyclic form) of the aldoses with three to six carbon atoms, page 54 Structures, with systematic and trivial names, of the 2-ketoses with three to six carbon atoms, page 55 Retained names of α-amino acids, page 103 Amino acids with trivial names (other than those in Table 10.3), page 109 IU PA C 10.3 10.4 Parent structures for natural products and related compounds Pr o 10.1 10.2 ion 6.2 Suffixes to denote peroxols (hydroperoxides) modified by functional replacement nomenclature (in decreasing order of seniority as principal group), page 58 Halides and pseudohalides, page 139 vis 6.1 Page of 1306 en da tio ns 4.3 v DRAFT October 2004 Preferred IUPAC Names Chapter 1, September, 2004 en da tio ns CHAPTER P-1 NOMENCLATURE OF ORGANIC COMPOUNDS P-10 P-11 P-12 P-13 P-14 P-15 P-16 Introduction Scope of nomenclature of organic compounds Preferred, preselected and retained names Operations in nomenclature General rules Types of nomenclature Name writing m P-10 Introduction IU PA C Pr o vis ion al Re co m For nomenclature purposes, a structure containing at least one carbon atom is considered to be an organic compound The formation of a systematic name for an organic compound requires selection and then naming of a parent structure This basic name may then be modified by prefixes, infixes, and, in the case of a parent hydride, suffixes, which convey precisely the structural changes required to generate the compound in question from the parent structure In contrast to such systematic names, there are traditional names which are widely used in industry and academic circles Examples are acetic acid, benzene and pyridine Therefore, when they meet the requirements of utility and when they fit into the general pattern of systematic nomenclature, these traditional names are retained A major new principle is elaborated in these Recommendations The concept of ‘preferred IUPAC names’ is developed and systematically applied Up to now, the nomenclature developed and recommended by IUPAC has emphasized the generation of unambiguous names in accord with the historical development of the subject In 1993, due to the explosion in the circulation of information and the globalization of human activities, it was deemed necessary to have a common language that will prove important in legal situations, with manifestations in patents, export-import regulations, environmental and health and safety information, etc However, rather than recommend only a single ‘unique name’ for each structure, we have developed rules for assigning ‘preferred IUPAC names’, while continuing to allow alternatives in order to preserve the diversity and adaptability of the nomenclature to daily activities in chemistry and in science in general Thus, the existence of preferred IUPAC names does not prevent the use of other names to take into account a specific context or to emphasize structural features common to a series of compounds Preferred IUPAC names belong to ‘preferred IUPAC nomenclature’ Any name other than a preferred IUPAC name, as long as it is unambiguous and follows the principles of the IUPAC recommendations herein, is acceptable as a ‘general’ IUPAC name, in the context of ‘general’ IUPAC nomenclature The concept of preferred IUPAC names is developed as a contribution to the continuing evolution of the IUPAC nomenclature of organic compounds This book (Recommendations 2004) covers and extends the principles, rules and conventions described in two former publications: Nomenclature of Organic Chemistry, 1979 Edition (ref 1) and A Guide to IUPAC Nomenclature of Organic Compounds, Recommendations 1993 (ref 2) In a few instances, the 1979 rules and the 1993 recommendations have been modified to achieve consistency within the entire system In case of divergence among the various recommendations, Recommendations 2004 prevail DRAFT October 2004 Page of 1306 Preferred IUPAC Names Chapter 1, September, 2004 P-11 Scope of nomenclature for organic compounds en da tio ns For nomenclature purposes we consider all compounds containing carbon as organic compounds Oxygen and nitrogen are two elements usually associated with carbon to form the system of functions or characteristic groups Other elements, among them the halogens and sulfur, complete the basic core of elements found in organic compounds Substitutive nomenclature was first applied to compounds containing this set of atoms The success of this type of nomenclature was such that it was extended to all elements of Groups 14, 15, 16, 17 and, in Group 13, to boron; it is now fully extended to all elements of Group 13 Table 1.1 Elements included in these recommendations 14 15 B boron C carbon N nitrogen Al aluminium Si silicon Ga gallium Ge germanium In indium Sn tin S sulfur Cl chlorine As arsenic Se selenium Br bromine Sb antimony Te tellurium I iodine Bi bismuth Po polonium As astatine m F fluorine co P phosphorus Re Pb lead 17 O oxygen ion Tl thallium 16 m 13 al Groups IU PA C Pr o vis The ending ‘ane’, characteristic of alkanes, was borrowed from methane, ethane, etc., and glued to terms forming the roots of the names of the various elements, for example sulfane, H2S; phosphane, PH3; silane, SiH4; alumane, AlH3 The resulting names constitute the basis of substitutive nomenclature; this treatment of parent hydrides is called generalized ‘ane’ nomenclature because all the rules applicable to alkanes are applicable to all hydrides of the elements of Groups 13, 14, 15, 16 and 17 The nomenclature of hydrides of carbon may be conveniently termed ‘carbane nomenclature’; whereas the term ‘heterane nomenclature’ covers the hydrides of elements other than carbon Names of mononuclear parent hydrides are listed in Table 2.1 in Chapter Organometallic compounds, i.e., compounds in which one or more carbon atom(s) is (are) directly attached to a metal atom, were always regarded as organic compounds for nomenclature purposes This association is maintained in these recommendations (see P-69), for the metals, semimetals, and nonmetals included in Groups 13, 14, 15, 16, and 17 The nomenclature for other organic derivatives of the elements in Groups through 12 is considered as part of the nomenclature of inorganic compounds The construction of systematic names is based on general nomenclature operations and rules, and on operations and rules specific to different types of nomenclature These aspects are discussed in the following sections Page of 1306 DRAFT October 2004 Preferred IUPAC Names Chapter 1, September, 2004 P-12 Preferred, preselected and retained IUPAC names ion al Re co m m en da tio ns P-12.1 ‘Preferred IUPAC names’ are names that are preferred among two or more names for the same structure generated from two or more recommended IUPAC rules or the many synonyms that have been coined and used over the years Preferred IUPAC names, or PINs, for short, are names selected according to the set of principles, conventions, and rules given herein They originate from the strict application of the rules; in this sense, they can be referred to as ‘single names’ All preferred IUPAC names are identified by the parenthetical abbreviation ‘(PIN)’ following the name Names used in the past, but now discarded or no longer recommended, are sometimes mentioned as a link to past rules and recommendations and are identified by words such as ‘not’ or ‘formerly’ or phrases like ‘no longer recommended’ It is necessary to select a preferred alternative in many instances in the construction of the names of organic compounds Preferred IUPAC names are given to parent structures and to characteristic groups denoted by prefixes and suffixes They also result from the choice to be made among the different types of nomenclature, for example, substitutive nomenclature, functional class nomenclature and multiplicative nomenclature; and among the different types of operations, for example substitutive, additive and subtractive Most commonly, a parent structure is a parent hydride, i.e., a structure containing, in addition to one or more hydrogen atoms, a single atom of an element, for example, methane; or a number of atoms (alike or different) linked together to form an unbranched chain, for example, pentane; or a monocyclic or polycyclic ring system, for example, cyclohexane and quinoline Methane is a retained name (see P-12.3) that is preferred to the systematic name ‘carbane’, a name never recommended to replace methane, but used to derive the names ‘carbene’ and carbyne for the radicals :CH2 and :CH·, respectively The name ‘pentane’ is formed by application of P-21.2.1 and is marked as the preferred IUPAC name, or PIN, even though no rule has been cited giving an alternative name The same reasoning applies to cyclohexane, a IUPAC name resulting from the application of P-22.1.1 The name ‘quinoline’ is a retained name that is preferred to the systematic alternative fusion names ‘1-benzopyridine’ and ‘benzo[b]pyridine’ methane (preferred IUPAC name or PIN, a retained name) carbane Pr o CH4 vis Examples: PA C CH3-CH2-CH2-CH2-CH3 IU cyclohexane (PIN) pentane (preferred IUPAC name or PIN) N quinoline (PIN, a retained name) 1-benzopyridine (a systematic fusion name) benzo[b]pyridine (a systematic fusion name) DRAFT October 2004 Page of 1306 Preferred IUPAC Names Chapter 1, September, 2004 en da tio ns It is sometimes convenient to employ parent hydrides of more complex structure, such as ring or ring-chain assemblies, for example biphenyl and styrene The name ‘1,1′-biphenyl’ results from the application of Rule P-28.2.1; it is the preferred IUPAC name and the locants 1,1′ are compulsory; the name ‘biphenyl’, without locants, can be used in general IUPAC nomenclature The name ‘styrene’ is a retained name and is preferred to the systematic substitutive names ‘vinylbenzene’, ‘ethenylbenzene’, ‘phenylethene’ and ‘phenylethylene’, that are acceptable in general IUPAC nomenclature as being clear and unambiguous CH=CH2 styrene (PIN, a retained name) vinylbenzene ethenylbenzene phenylethene phenylethylene co m m 1,1′-biphenyl (PIN) biphenyl Re A special class of parent structures having retained names (see P-12.3) is called functional parents, for example acetone and acetic acid These two names are preferred IUPAC names; the corresponding systematic alternatives, propan-2-one and ethanoic acid, may be used in general IUPAC nomenclature CH3-CO-CH3 al CH3-COOH ion acetone (PIN) propan-2-one acetic acid (PIN) ethanoic acid vis In order to generate the parent structure from a compound to be named, various formal operations must be carried out For example, in naming the structure below, the parent hydride ‘pentane’ is formally derived by replacing the oxygen and chlorine atoms by the appropriate number Pr o O ║ ClCH2-CH2-CH2-C-CH3 IU PA C of hydrogen atoms For constructing the name, the formal operation is reversed; the suffix ‘one’ and the prefix ‘chloro’, indicating substitution of the hydrogen atoms of pentane, are attached to the name of the parent hydride to give the name ‘5-chloropentan-2-one’ Suffixes and prefixes can represent a number of different types of formal operations on the parent structure Frequently, the suffix or prefix denotes the attachment of a characteristic group (functional group), for example, ‘one’ or ‘oxo’ for =O A prefix may also describe a group derived from a parent hydride, for example ‘pentyl’, from pentane, for CH3-CH2-CH2-CH2-CH2− The substitutive operation, described in P-13.1, is the operation used most extensively in organic nomenclature Indeed, the comprehensive nomenclature system based largely on the application of this operation to parent structures is, for convenience, termed substitutive nomenclature, although Page of 1306 DRAFT October 2004 Preferred IUPAC Names Chapter 1, September, 2004 IU PA C Pr o vis ion al Re co m m en da tio ns this nomenclature also involves many of the other types of operations described in P-13 Substitutive nomenclature is the set of substitutive names and principles, conventions, and rules used for name construction Examples of substitutive and other nomenclature operations are shown in Table 1.2 Another type of nomenclature expresses the principal characteristic group not as a suffix but as a term denoting the functional class cited in a name as a separate word; in Table 1.2, the name ‘ethyl propyl ether’ is a typical functional class name based on the functional class name ‘ether’ The corresponding substitutive name ‘1-ethoxypropane’ is constructed by using the prefix ‘ethoxy’ and the parent hydride name ‘propane’ Substitutive and functional class names are written differently Generally, substitutive names are unitary names that combine prefixes, names of parent hydrides, endings and suffixes in one word On the contrary, a functional class name is written as separate words, even though the part describing the parent hydride or the modified parent hydride is the result of the same operations used to construct substitutive names The great majority, if not all, of organic compounds can be named in accordance with the principles of substitutive and functional class operations However, in these recommendations, where there is a choice, names obtained by the substitutive operation are preferred IUPAC names In Table 1.2, examples 1, and illustrates this preference The substitutive names ethoxypropane and 2chloropentan-2-one are preferred to the functional class names based on the names of the corresponding class, ether and ketone, ethyl propyl ether and 2-chloropropyl methyl ketone On the contrary, a functional class name is preferred for the ester trimethyl phosphite over the substitutive name trimethoxyphosphane Esters, along with acid halides and anhydrides are preferably named by using functional class nomenclature; substitutive nomenclature is not adapted to naming these classes Other types of operations are widely used, alone or along with substitutive nomenclature The skeletal replacement operation (often referred to as ‘a’ replacement) is used as a necessary complement in order to introduce heteroatoms into cyclic hydrocarbons and to avoid the proliferation of prefixes in names for acyclic systems For example, the name formed by skeletal replacement ‘2,5,8,11-tetraoxatridecane’ is preferred to the substitutive name ‘1-ethoxy-2-[2(methoxyethoxy)ethoxy]ethane’ Additive and subtractive operations have been extended for naming radicals and ions They are the sole method for modification of the degree of hydrogenation, by adding or subtracting pairs of hydrogen atoms Examples and illustrate the preference for substitutive operations over additive or subtractive operations The conjunctive operation eliminates hydrogen atoms from two different compounds and then combines them; this method is used to name parent hydrides composed of repeated identical units or to link rings and chains under specific conditions Example in Table 1.2 illustrates such an operation; in IUPAC nomenclature, however, a substitutive name is always preferred to a conjunctive name, for example ‘1H-indol-1ylacetic acid’ is preferred to ‘1H-indole-1-acetic acid’ DRAFT October 2004 Page 10 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 m −CH= CH3-O− CH3-O-C(=NH)− CH3-O-CS− CH3-O-CO− CH3-P(O)(NCO)– CH3-O-S− CH3-O-S(=NH)− CH3O-SO-O− CH3-O-SO2− CH3O-SO2-NH− CH3-O-SO2− PA C Pr o 2-methylphenyl* = o-tolyl IU 3-methylphenyl* = m-tolyl 4-methylphenyl* = p-tolyl methyl(phenyl)arsinoyl* P-29.3.2.2 P-63.2.2.2 P-65.6.3.3.1 P-65.6.3.3.1 P-65.6.3.2.2 P-67.1.4.1.1 P-63.3.2 P-65.3.2.3 P-67.1.4.4.2 P-65.3.2.3; P-67.1.4.4.1 P-67.1.4.4.2 P-65.3.2.3; P-67.1.4.4.1 P-29.3.1 P-66.1.1.4.1 P-29.4 P-29.4 P-29.4 CH3-SeSe– CH3-SS– CH3-TeTe– −CH2− −O-CH2-O− −S-CH2-S− P-63.3.1 P-63.3.1 P-63.3.1 P-29.6 P-63.2.2.1.3 P-63.2.2.1.3 CH2=C(CH3)− P-32.1.1 (CH3)2CH− P-29.4; P-29.6 (CH3)2C= (CH3)2C-O– CH2= C=N-O– P-29.4; P-29.6 P-63.2.2.1.1 P-29.3.1 P-61.9 CH≡ CH3-OO− P-29.3.1 P-63.3.1 Re co m CH3− CH3-NH-SO− CH3-CH2-CH2-CH(CH3)− CH3-CH2-CH(CH3)-CH2− (CH3)2CH-CH2-CH2− al vis ion methanyl: see methyl* methanylidene: see methylidene* methanylidyne: see methylidyne* methanylylidene* methoxy* (not methyloxy) C-methoxycarbonimidoyl* methoxycarbonothioyl* methoxycarbonyl* (not carbomethoxy) methoxy(isocyanato)phosphoryl* methoxysulfanyl* (not methoxythio) S-methoxysulfinimidoyl* (methoxysulfinyl)oxy* methoxysulfonyl* = methoxysulfuryl (methoxysulfonyl)amino* methoxysulfuryl = methoxysulfonyl* methoxythio: see methoxysulfanyl* methyl* (not methanyl) (methylamino)sulfinyl* 1-methylbutyl = pentan-2-yl* 2-methylbutyl* 3-methylbutyl* (not isopentyl) methyldioxy: see methylperoxy* methyldiselanyl* methyldisulfanyl* methylditellanyl* methylene* (not methanediyl) methylenebis(oxy)* (not methylenedioxy) methylenebis(sulfanediyl)* 1-methylethenyl = prop-1-en-2-yl* =isopropenyl 1-methylethyl = propan-2-yl* = isopropyl 1-methylethylidene = propan-2-ylidene* = isopropylidene (1-methylethyl)oxy = propan-2-yloxy* methylidene* (not methanylidene) (λ2-methylideneamino)oxy* (not fulminato) methylidyne* (not methanylidyne) methylperoxy* (not methyldioxy) methyloxy (see methoxy*) en da tio ns 18 CH3 (C6H5)(CH3)As(O)− DRAFT October 2004 P-29.6 P-29.6 P-29.6 P-67.1.4.1.1 Page 1292 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 19 CH3-P(O)< P-67.1.4.1.1 (CH3)3C− P-29.4; P-29.6 en da tio ns methylphosphonoyl* 2-methylpropan-2-yl = tert-butyl* (unsubstsituted) = 1,1-dimethylethyl (2-methylpropan-2-yl)oxy = tert-butoxy* 2-methylpropan-2-ylium-1-yl* (CH3)3C-O− CH3-C+(CH3)-CH2– P-63.2.2.2 P-73.6 2-methylprop-2-enoyl* = methacryloyl CH2=C(CH3)-CO− P-65.1.7.3.1 1-methylprop2-en-1-yl = but-3-en-2-yl* 1-methylpropyl = butan-2-yl* (1-methylpropyl)oxy = butan-2-yloxy* = sec-butoxy CH2=CH-CH-CH3 CH3-CH2-C(CH3)− CH3-CH2-(CH3)CH-O− | ion vis Pr o PA C morpholin-4-yl* (not morpholino) m CH3-Se− P-63.2.2.1.2; P-63.2.5 CH3-S(=NH)(O)− CH3-+S< P-65.6.3.2.2.2 P-73.6 CH3-Te− P-63.2.2.1.2; P-63.2.5 co P-73.6 P-63.2.2.1.2 P-63.3.2 P-65.6.3.2.2.2 SiH3-SiH2-SiH2-SiH(CH3)− CH3-S-SO2− CH3-SSS− C=N-O− O N P-29.4 P-65.6.3.3.1 P-68.4.1.3 P-61.9 P-29.3.3 CO _ P-65.1.7.4.2 naphthalene-1-carbonyl* = 1-naphthoyl P-65.1.7.4.2 IU naphthalene-2-carbonyl* = 2-naphthoyl Page 1293 of 1306 P-73.6 CH3-+S< CH3-S− CH3-S-O– CH3-S(=NH)− Re al methylselanyl* (not methylseleno) methylseleninyl: see methaneseleninyl* methylseleno: see methylselanyl* methylsulfaniumdiyl* = methylsulfoniumdiyl methylsulfanyl* (not methylthio) (methylsulfanyl)oxy* S-methylsulfinimidoyl: see methanesulfinimidoyl* methylsulfinyl: see methanesulfinyl* S-methylsulfonimidoyl: see methanesulfonimidoyl* methylsulfoniumdiyl = methylsulfaniumdiyl* methylsulfonyl: see methanesulfonyl* methyltellanyl* (not methyltelluro) methyltelluro: see methyltellanyl* 1-methyltetrasilan-1-yl* methylthio: see methylsulfanyl* (methylthio)oxy: see methylsulfanyl)oxy* (methylthio)sulfonyl = (methylsulfanyl)sulfonyl* methyltrisulfanyl* = methyltrithio (λ2-methylideneamino)oxy* morpholino: see morpholin-4-yl* N m + H 3C 1-methylpyridin-1-ium-4-yl* P-32.1.1 P-29.3.2.2 P-63.2.2.1.1 DRAFT October 2004 Preferred IUPAC Names Appendix 2, September, 2004 20 naphthalen-1-yl* - 1-naphthyl naphthalen-2-yl* = 2-naphthyl naphthalene-2(1H)-ylidene* (also 1(2H)-isomer) 2 P-29.3.4.1;P-29.6 P-29.3.4.1 P-29.3.4.2 m naphthalene-2,3-diylidene* m en da tio ns co C10H7-CO− C10H7-CO− C10H7− C10H7− Re 1-naphthoyl = naphthalene-1-carbonyl* 2-naphthoyl = naphthalene-2-carbonyl* 1-naphthyl = naphthalen-1-yl* 2-naphthyl = naphthalen-2-yl* P-65.1.7.3.1 P-65.1.7.3.1 P-29.3.4.1; P-29.6 P-29.3.4.1; P- N PA C Pr o vis ion nitramido* nitridophosphoryl = phosphoronitridoyl* nitrilo* (not azanetriyl) nitro* aci-nitro: see hydroxy(oxo)-λ5-azanylidene* nitrooxy* nitroryl = azoryl* nitroso* nonanoyl* nonan-1-yl: see nonyl* nonan-1-ylidene: see nonylidene* nonan-1-ylidyne: see nonylidyne* nonyl* (not nonan-1-yl) nonylidene* (not nonan-1-ylidene) nonylidyne* (not nonanylidyne) al nicotinoyl = pyridine-3-carbonyl* octadecanoyl* = stearoyl IU octadecan-1-yl: see octadecyl* (Z)-octadec-9-enoyl* = oleoyl octadecyl* (not octadecan-1-yl) octanoyl* octan-1-yl: see octyl* CO P-65.1.7.3.1 _ O2N-NH– P(≡N)< –N< O2N− P-67.1.4.3 P-67.1.4.1 P-62.2.1.2.3 P-61.5.1 O2N-O– −N(O)< O=N− CH3-[CH2]7-CO– P-67.1.4.3 P-67.1.4.1.1 P-61.5.1 P-65.1.7.4.1 CH3-[CH2]8− CH3-[CH2]7-CH= CH3-[CH2]7-C≡ P-29.3.2.1 P-29.3.2.1 P-29.3.2.1 CH3-[CH2]16-CO− P-65.1.7.3.1 CH3-[CH2]7-CH=CH-[CH2]7-COCH3-[CH2]17− CH3-[CH2]7-CO− DRAFT October 2004 P-65.1.7.3.1 P-29.3.1 P-65.1.7.4.1 Page 1294 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 21 P-29.3.2.1 P-29.3.2.1 P-29.3.2.1 P-65.1.7.3.1 P-65.2.3.3 ion al Re co m m en da tio ns octan-1-ylidene: see octylidene* octan-1-ylidyne: see octylidyne* octyl* (not octan-1-yl) CH3-[CH2]7− octylidene* (not octan-1-ylidene) CH3-[CH2]6-CH= octylidyne* (not octan-1-ylidyne) CH3-[CH2]6-C≡ oleoyl = (Z)-octadec-9-enoyl* CH3-[CH2]7-CH=CH-[CH2]7-CO− oxaldehydoyl* = hydrooxalyl (not formylcarbonyl) HOC-CO− oxalo* = carboxycarbonyl (not carboxyformyl, nor hydroxyl(oxo)acetyl) HO-CO-CO− oxaloamino* = (carboxycarbonyl)amino HO-CO-CO-NH− oxalooxy* = (carboxycarbonyl)oxy HO-CO-CO-O− oxalosulfanyl* = (carboxycarbonyl)sulfanyl HO-CO-CO-S− −CO-CO− oxalyl* = ethanedioyl = dioxoethane-1,2-diyl oxalylbis(azanediyl)* –HN-CO-CO-NH– oxalylbis(azanediylidene)* =N-CO-CO-N= oxalyldinitrilo* >N-CO-CO-N< oxamoyl* (not carbamoylcarbonyl, nor carbamoylformyl, nor amino(oxo)acetyl) H2N-CO-CO− oxamoylamino* = carbamoylformamido = aminooxoacetamido H2N-CO-CO-NH– oxamoylazanediyl* H2N-CO-CO-N< oxamoylimino* H2N-CO-CO-N= − O– oxido* oxo* (not keto) O= oxoacetyl: see hydrooxalyl* O=NH2− oxo-λ5-azanyl* (oxo-λ5-azanylidyne)methyl* (not fulminato) ONC– vis oxolan-3-yl-4-ylidene* PA C Pr o oxomethylidene* oxo-λ5-phosphanylidene* oxo-λ5-phosphanylidyne* 2-oxopropyl* = acetonyl 2-oxopropylidene* (not acetonylidene) 2-oxopropylidyne* (not acetonylidyne) oxy* palmitoyl = hexadecanoyl* IU pentanedioyl* = glutaryl pentanoyl* pentan-1-yl: see pentyl* pentan-2-yl* = 1-methylbutyl pentan-1-ylidene: see pentylidene* pentan-3-ylidene* = 1-ethylpropylidene pentan-1-ylidyne: see pentylidyne* Page 1295 of 1306 P-65.2.3.3 P-65.2.3.3 P-65.2.3.3 P-65.2.3.3 P-65.2.3.3 P-66.1.5.3 P-66.1.5.3 P-66.1.5.3 P-65.2.3.3 P-66.1.5.3 P-66.1.5.3 P-66.1.5.3 P-72.6.2 P-64.5 P-62.5 P-61.9; P-66.5.3 O P-29.3.3 =C=O HP(O)= P(O)≡ CH3-CO-CH2− CH3-CO-CH= CH3-CO-C≡ −O− P-65.2.1.8 P-67.1.4.1.1 P-67.1.4.1.1 P-56.1.2; 64.5.1 P-56,1,2 P-56.1.2 P-63.2.2.1.1 CH3-[CH2]14-CO− P-65.1.7.3.1 −CO-CH2-CH2-CH2-CO− CH3-CH2-CH2-CH2-CO− P-65.1.7.3.1 P-65.1.7.4.1 CH3-CH2-CH2-CH(CH3)− P-29.4 (CH3-CH2)2C= DRAFT October 2004 P-29.3.2.2; P-29.4 Preferred IUPAC Names Appendix 2, September, 2004 22 P-67.1.4.1.1 m P(O)(OOH)< C6H5-O− C6H5− C6H5-NH− C6H5-NH-SO2− C6H5-N=N− C6H5-CO− P-63.2.2.2 P-29.6 P-62.2.1.1.3 P-66.1.1.4.1 P-68.3.1.3.1.2 P-65.1.7.1.2 C6H5-P(O)Cl− C6H5-N=N− P-67.1.4.1.1 P-68.3.1 ion al Re phenoxy* (not phenyloxy) phenyl* phenylamino = anilino* (phenylamino)sulfonyl = phenylsulfamoyl* phenylazo = phenyldiazenyl* phenylcarbonyl = benzoyl* phenyl(chlorophosphonoyl) = phenylphosphonochloridoyl* phenyldiazenyl* = phenylazo 10 co 1 vis 1,2-phenylene* (not benzene-1,2-diyl) P-29.6 P-29.6 P-29.6 C6H5-CH=CH− P-29.6 C6H5-CH2− C6H5-CH= C6H5-C≡ P-29.6 P-29.6 P-29.6 C6H5P(O)(Cl)− C6H5-CH=CH-CO− C6H5-Se− C6H5-Se-O− P-67.1.4.1.1 P-67.1.7.3.1 P-63.2.2.1.2; P-63.2.5 P-63.4.2 IU PA C Pr o 1,3-phenylene* (not benzene-1,3-diyl) 1,4-phenylene* (not benzene-1,4-diyl) 2-phenylethenyl* = 2-phenylvinyl = styryl phenyloxy: see phenoxy* phenylmethyl = benzyl* phenylmethylidene =benzylidene* phenylmethylidyne = benzylidyne* phenylphosphonochloridoyl* = phenyl(chlorophosphonoyl) 3-phenylprop-2-enoyl* = cinnamoyl phenylselanyl* (not phenylseleno) (phenylselanyl)oxy* phenylseleno: see phenylselanyl* phenylselenonyl: see benzeneselenonyl* P-29.3.4.1;P-29.6 m phenanthren-9-yl* =9-phenanthryl (also 1-, 2-, 3-, and 4- isomers) P-65.1.7.4.1 P-29.3.2.1 P-29.3.2.1 P-29.3.2.1 P-63.2.2.1.1 P-61.3.2 P-61.3.2 P-61.3.2 P-61.3.2 P-63.3.1 en da tio ns CH3-CH2-CH=CH-CO− CH3-CH2-CH2-CH2-CH2− CH3-CH2-CH2-CH2-CH= CH3-CH2-CH2-CH2-C≡ CH3-[CH2]3-CH2-O− O3Br– O3Cl− O3F– O3I− −OO− pent-2-enoyl* pentyl* (not pentan-1-yl) pentylidene* (not pentan-1-ylidene) pentylidyne* (not pentan-1-ylidyne) pentyloxy* perbromyl* perchloryl* perfluoryl* periodyl* peroxy* (not dioxy) peroxycarboxy: see carbonoperoxoyl* peroxyphosphoryl = phosphoroperoxoyl* DRAFT October 2004 Page 1296 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 23 phosphinane-3,5,diyl* C6H5-S− C6H5-Se-O− P-66.1.1.4.1 en da tio ns C6H5-CH=CH– HP< −P< H3P+− H2P− H4P− HP= −P= co C6H5-NH-SO2− phenylsulfamoyl* = (phenylamino)sulfonyl =anilinosulfonyl phenylsulfanyl* (not phenylthio) (phenylsulfanyl)oxy* phenylsulfinoselenoyl: see benzenesulfinoselenoyl* phenylsulfinyl; see benzenesulfinyl* phenylsulfonyl: see benzenesulfonyl* phenyltellanyl* (not phenyltelluro) (phenyltellanyl)oxy* phenyltelluro: see phenyltellanyl* phenylthio: see phenylsulfanyl* 2-phenylvinyl = 2-phenylethenyl* = styryl phosphanediyl* (not phosphinediyl) phosphanetriyl* (not phosphinetriyl) phosphaniumyl* = phosphonio phosphanyl* (not phosphino) λ5-phosphanyl* = phosphoranyl phosphanylidene* phosphanylylidene* P-63.2.2.1.2 P-63.4.2 C6H5-Te− C6H5-Te-O− m m P-63.2.2.1.2 P-63.4.2 P-29-6 P-68.3.2.4.2.2 P-68.3.2.4.2.2 P-73.6 P-29.3.1 P-68.3.2.4.2.2 P-68.3.2.4.2.2 P-68.3.2.4.2.2 Re PH Pr o vis ion al phosphinimidoyl* = imidophosphinoyl phosphino: see phosphanyl* phosphinothioyl* phosphinoyl* phospho* phosphonato* phosphonio = phosphaniumyl* phosphono* phosphonooxy* phosphonothioyl* = hydro(thiophosphoryl) phosphonoyl* = hydrophosphoryl phosphooxy* phosphoramidochloridoyl* = chloroamidophosphoryl phosphoranyl = λ5-phosphanyl* phosphorodichloridoyl* = dichlorophosphoryl IU PA C phosphoronitridoyl* = nitridophosphoryl phosphorocyanidoisocyanatidothioyl* = cyano(isocyanato)phosphorothioyl = cyano(isocyanato)(thiophosphoryl) phosphorohydrazidimidoyl* = hydrazidimidophosphoryl phosphoroperoxoyl* = peroxyphosphoryl phosphoroso* phosphoro(thioperoxoyl)* = (thioperoxy)phosphoryl phosphorothioyl* = thiophosphoryl Page 1297 of 1306 P-29.3.3 H2P(=NH)− P-67.1.4.1.1 H2P(S)− H2P(O)– PO2P– (−O)P(O)− H3P+− (HO)2P(O)− (HO)2P(O)-O− >PH(S) HP(O)< O2P-O− P(O)(NH2)Cl– H4P− P(O)Cl2– P-67.1.4.1.1 P-67.1.4.1.1 P-61.5.5 P-72.6.1 P-73.6 P-67.1.4.1.1 P-67.1.4.1.3 P-67.1.4.1.1, P-67.1.4.1.2 P-67.1.4.1.1, P-67.1.4.1.2 P-67.1.4.3 P-67.1.4.1.1 P-68.3.2.4.2.2 P-67.1.4.1.1 P(≡N)< P-67.1.4.1.1 −P(S)(CN)(NCO) P-67.1.4.1.1 >P(=NH)(NHNH2) >P(O)(OOH) –PO >P(O)(OSH) or >P(O)(SOH) >P(S)– DRAFT October 2004 P-67.1.4.1.1 P-67.1.4.1.1 P-61.5.5 P-67.1.4.1.1 P-67.1.4.1.1 Preferred IUPAC Names Appendix 2, September, 2004 24 −P(O)< CO phthaloyl = benzene-1,2-dicarbonyl* (not 1,2-phenylenedicarbonyl) P-67.1.4.1.1 _ en da tio ns phosphoryl* P-65.1.7.3.1 CO _ piperidino: see piperidin-1-yl* PA C propanethioyl* = thiopropionyl propanimidoyl* = propionimidoyl propanoyl* = propionyl propanoylamino = propanamido* = propionamido = propionylamino propanoyloxy* = propionyloxy propan-1-yl: see propyl* propan-2-yl* = isopropyl = 1-methylethyl propan-1-ylidene: see propylidene* m P-29.6 co P-29.6 P-29.6 P-68.2.2 P-68.2.2 P-68.2.2 P-68.2.2 −PbH= H3Pb− P-68.2.2 P-68.2.2 H2Pb= HPb≡ P-68.2.2 P-68.2.2 CH3-CH2-CO-NH− −(HN)C-CH2-C(NH)− −CO-CH2-CO− −CH2-CH2-CH2− −CH2-CH(CH3)− P-66.1.1.4.2 P-65.1.7.4.1 P-65.1.7.3.1 P-29.3.2.2 P-29.3.2.2 al Re H2Pb< =Pb= >Pb< −PbH< ion vis Pr o propane-1-1-1-triyl IU NH m piperidin-4-yl* = 4-piperidyl (and 2- and 3- isomers) 1-piperidyl = piperidin-1-yl* (not piperidino) 4-piperidyl = piperidin-4-yl* plumbanediyl* (not plumbylene) plumbanediylidene* plumbanetetrayl* plumbanetriyl* plumbanyl:see plumbyl* plumbanylidene : see plumbylidene* plumbanylidyne: see plumbylidyne* plumbanylylidene* plumbyl* (not plumbanyl) plumbylene: see plumbanediyl* plumbylidene* (not plumbanylidene) plumbylidyne* (not plumbanylidyne) propanamido* = propanoylamino = propionamido = propionylamino propanediimidoyl* = malonimidoyl propanedioyl* = malonyl propane-1,3-diyl* (not trimethylene) propane-1,2-diyl* = 1-methylethane-1,2-diyl (not propylene) P-29.6 N piperidin-1-yl* = 1-piperidyl (not piperidino) CH3CH2C P-29.3.2.2 CH3-CH3-CS– CH3-CH2-C(=NH)– CH3-CH2-CO− CH3-CH2-CO-NH− P-65.1.7.4.1 P-65.1.7.4.1 P-65.1.7.3.1 P-66.1.1.4.2 CH3-CH2-CO-O− P-65.6.3.2.2 (CH3)2CH− P-29.4; P-29.6 DRAFT October 2004 Page 1298 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 25 (CH3)2C= (CH3)2CH-O− │ CH3-CH2-C= propan-1-yl-1-ylidene* propan-1-ylidyne: see propylidyne* prop-2-enehydrazonoyl* = acrylohydrazonoyl P-65.1.7.3.2 CH2=CH-CO− CH2=CH-CSe− CH3-CH=CH− P-65.1.7.3.1 P-65.1.7.3.3 P-32.3 CH2=C(CH3)− CH2=CH-CH2− CH2=CH-CH= CH2=CH-C≡ CH3-CH2-CO-NH− P-32.1.1 P-32.3 P-32.3 P-32.3 P-66.1.1.4.2 CH3-CH2-C(=NH)CH3-CH2-CO− P-65.1.7.4.1 P-65.1.7.3.1 CH3-CH2-CO-NH− CH3-CH2-CO-O− CH3-CH2-CH2-O− P-66.1.1.4.2 P-65.6.3.2.2 P-63.2.2.2 CH3-CH2-CH2− CH3-CH2-C= CH3-CH2-C≡ P-29.3.2.1 P-29.3.2.1 P-29.3.2.1 m co Re + N P-73.6 vis piperidino = piperidin-1-ium-1-yl* CH2=CH-C(=NNH2)− ion propyloxy: see propoxy* al propyl* (not propan-1-yl) propylidene* (not propan-1-ylidene) propylidyne* (not propan-1-ylidyne) PA C Pr o pyridin-1-ium-1-yl* = pyridinio pyridin-1(4H)-yl* P-73.6 N IU P-29.3.4.1 1 N pyridin-2-yl* = 2-pyridyl (and 3- and 4- isomers) P-29.3.4.1; P-29.6 N pyridine-3-carbonyl* = nicotinoyl Page 1299 of 1306 P-29.3.2.2 m prop-2-enoyl* = acryloyl prop-2-eneselenoyl* = selenoacryloyl prop-1-en-1-yl* prop-1-en-2-yl* = 1-methylethen-1-yl = isopropenyl prop-2-en-1-yl* = allyl prop-2-en-1-ylidene* = allylidene prop-2-en-1-ylidyne* = allylidyne propionamido= propanamido* = propionylamino = propanoylamino propionimidoyl = propanimidoyl* propionyl = propanoyl* propionylamino = propanamido* = propanoylamino = propionamido propionyloxy = propanoyloxy* propoxy* (not propyloxy) P-29.4; P-29.6 P-63.2.2.2 en da tio ns propan-2-ylidene* = 1-methylethylidene = isopropylidene propan-2-yloxy* = isopropoxy P-65.1.7.3.1 CO _ DRAFT October 2004 Preferred IUPAC Names Appendix 2, September, 2004 26 N 2-pyridyl = pyridin-2-yl* (and 3-, 4-isomers) pyruvoyl: see 2-oxopropanoyl* CO _ CH3-CO-CO− N quinolin-2-yl* = 2-quinolyl (and 3-, 4-, 5-, 6-, 7-, and 8- isomers) 2-quinolyl = quinolin-2-yl* P-29.3.4.1; P-29.6 P-65.1.7.4.1 P-29.6 P-29.6 ion vis Pr o P-63.1.5 P-73.6 P-63.1.5 P-67.1.4.1.1 P-64.6.1 co m m −Se− H2+Se– HSe− HP(O)(SeH)– Se= P-65.3.2.1 P-65.3.2.3 CH3-CSe– CH2=CH-CSe− NC-Se− SeHC– HO-Se– P-65.1.7.2.3 P-65.1.7.3.3 P-65.2.2 P-65.1.7.2.3 P-63.4.2.2 HO-Se-CH2− Se(=NH)(=S)< H2+Se– HO-SeO2− Se(O)(=NNH2)– SeO2< Se= P-63.4.2.2 P-65.3.2.3 P-73.6 P-65.3.2.1 P-65.3.2.3 P-65.3.2.3 P-64.6.1 H2N-CO-NHNH− P-68.3.1.2.4 Re HO-SeO− >Se=O al selanediyl* (not seleno) selaniumyl* = selenonio selanyl* (not hydroseleno) selanylphosphinoyl* selanylidene* = selenoxo seleneno: see hydroxyselanyl* selenino* (preferred when unmodified) seleninyl* seleno: see selanediyl* selenoacetyl = ethaneselenoyl* selenoacryloyl = prop-2-enselenoyl* selenocyanato* selenoformyl = metahnetelluroyl* selenohydroperoxy = hydroxyselanyl* (OS-selenohydroperoxy)methyl (hydroxyselanyl)methyl* = selenonimidothioyl* selenonio = selaniumyl* selenono* (preferred when unmodified) selenonohydrazonoyl* selenonyl* selenoxo = selanylidene* semicarbazido = 2-carbamoylhydrazin-1-yl* = 2-(aminocarbonyl)hydrazin-1-yl semicarbazono = 2-carbamoylhydrazin-1-ylidene* silanediyl* (not silylene) silanediyldiethane-1,2-diyl* = silanediyldiethylene silanediyldiethylene = silanediyldiethane-1,2-diyl* silanediylidene* silanetetrayl* silanetriyl* silanyl: see silyl* silanylidene : see silylidene* silanylidyne: see silylidyne* H2N-CO-NHN= H2Si< −CH2-CH2-SiH2-CH2-CH2− −CH2-CH2-SiH2-CH2-CH2− =Si= >Si< −SiH< P-68.3.1.2.5 P-68.2.2 P-29.5 P-29.5 P-68.2.2 P-68.2.2 P-68.2.2 IU PA C P-65.1.7.3.1 en da tio ns pyridin-4-carbonyl* = isonicotinoyl DRAFT October 2004 Page 1300 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 27 −SiH= ion vis Pr o PA C IU Page 1301 of 1306 P-68.2.2 en da tio ns H3Si− P-68.2.2 H2Si= HSi≡ H3Si-O− SiH3-SiH(SiH3)-SiH2-SiH2− H2Sn< =Sn= >Sn< −SnH< m m −SnH= H3Sn− P-68.2.2 P-68.2.2 P-68.2.6.2 P-29.4 P-68.2.2 P-68.2.2 P-68.2.2 P-68.2.2 P-68.2.2 P-68.2.2 P-29.3.1 P-68.2.2 P-65.1.7.3.1 P-68.3.2.4.2.2 P-68.3.2.4.2.2 P-73.6 P-68.3.2.4.2.2 P-68.3.2.4.2.2 P-68.3.2.4.2.2 P-68.3.2.4.2.2 H2Sb(=NH)− P-67.1.4.1.1 H2Sb(S)− H2Sb(O)– (−O)Sb(O)− H3Sb+− (HO)2Sb(O)− HSb(O)< H4Sb− Sb(≡N)< (H2N)2Sb(S)− >Sb(=NNH2)− >Sb(O)– P-67.1.4.1.1 P-67.1.4.1.1 P-72.6.1 P-73.6 P-67.1.4.1.1 P-67.1.4.1.1 P-68.3.2.4.2.2 P-67.1.4.1.1 P-67.1.4.1.1 P-67.1.4.1.1 P-67.1.4.1.1 co H2Sn= HSn≡ CH3-[CH2]16-CO− HSb< −Sb< H3Sb+− H2Sb− H4Sb− HSb= −Sb= Re al silanylylidene* siloxy: see silyloxy* silyl* (not silanyl) silylene: see silanediyl* silylidene* (not silanylidene) silylidyne* (not silanylidyne) silyloxy* (not siloxy) 3-silyltetrasilan-1-yl* stannanediyl* (not stannylene) stannanediylidene* stannanetetrayl* stannanetriyl* stannanyl: see stannyl* stannanylidene : see stannylidene* stannanylidyne: see stannylidyne* stannanylylidene* stannyl* (not stannanyl) stannylene: see stannanediyl* stannylidene* (not stannanylidene) stannylidyne* (not stannanylidyne) stearoyl = octadecanoyl* stibanediyl* (not stibinediyl) stibanetriyl* (not stibinetriyl) stibaniumyl* = stibonio stibanyl* (not stibino) λ5-stibanyl* = stiboranyl stibanylidene* stibanylylidene* stibinediyl : see stibanediyl* stibinetriyl : see stibanetriyl* stibinimidoyl* = dihydrostiborimidoyl stibino: see stibanyl* stibinothioyl* = dihydrostiborothioyl stibinoyl* stibonato* stibonio = stibaniumyl* stibono* stibonoyl* stiboranyl = λ5-stibanyl* stiboronitridoyl* stiborodiamidothioyl* stiborohydrazonoyl* = hydrazonostiboryl stiboryl* (not antimonyl) styryl = 2-phenylethen-1-yl* = 2-phenylvinyl succinyl = butanedioyl* succinimidoyl = butanediimidoyl* sulfamoyl* = aminosulfonyl sulfanediyl* (not thio) sulfanediylbis(methylene)* = sulfanediyldimethylene sulfanediyldimethylene = sulfanediylbis(methylene)* C6H5-CH=CH− −CO-CH2-CH2-CO− (HN=)C-CH2-CH2-C(=NH)– H2N-SO2− −S− −CH2-S-CH2− −CH2-S-CH2− DRAFT October 2004 P-29.6 P-65.1.7.3.1 P-65.1.7.3.2 P-65.3.2.3 P-63.1.5 P-63.2.2.1.3 P-63.2.2.1.3 Preferred IUPAC Names Appendix 2, September, 2004 28 m HS-O-CO-O− P-65.2.1.7 P(O)(O-SH)< P-67.1.4.1.1 co ion vis Pr o PA C IU sulfonylbis(sulfanediyl)* sulfonyldimethylene: see sulfonylbis(methylene)* P-65.2.4.1.5 P-65.1.5.1; P-65.2.1.6 P-65.2.1.6 P-64.6.1 P-65.2.1.8 P-63.4.2.2 m HS-O– P-67.1.4.1.1 P-65.3.2.3 HS-CS-S-CS− P-65.2.4.1.5 PH(S)(SH)– P-67.1.4.1.1 − S– S=(NH)< P-72.6.2 P-65.3.2.3 HO-S(O)− −S(S)− −SO− HO-SO2− − O-SO2– –S(O)(=NH)– H2S+− H2S+− –S(=NNH2)2– –S(=NH)2– –S(S)2– –S(O)(=NNH2)– –S(O)(S)– −SO2− −CH2-SO2-CH2− −O-SO2-O− P-65.3.2.1 P-65.3.2.3 P-65.3.2.3 P-65.3.2.1 P-72.6.1 P-67.1.4.4.1 P-73.6 P-73.6 P-67.1.4.4.1 P-67.1.4.4.1 P-65.3.2.3; P-67.1.4.4.1 P-65.3.2.3 ;P-67.1.4.4.1 P-65.3.2.3; P-67.1.4.4.1 P-65.3.2.3; P-67.1.4.4.1 P-65.3.2.3 P-65.3.2.3 −S-SO2-S− P-65.3.2.3 Re PH(S)(SH)– HS-SO-O− al (sulfanyloxy)phosphoryl* = (SO-thioperoxy)phosphoryl sulfanylphosphinothioyl* =sulfanyl(thiophosphinoyl) (sulfanylsulfinyl)oxy* [(sulfanylthiocarbonyl)sulfanyl]thiocarbonyl = [(dithiocarboxy)sulfanyl]carbonothioyl* = [(sulfanylcarbonothioyl)sulfanyl]carbonothioyl {not [(dithiocarboxy)sulfanyl]thioformyl} sulfanyl(thiophosphinoyl) = sulfanylphosphinothioyl* sulfeno: see hydroxysulfanyl* sulfide* sulfimidoyl* sulfinamoyl: see aminosulfinyl* sulfino* (preferred when unmodified) sulfinothioyl* sulfinyl* = thionyl sulfo* (preferred when unmodified) sulfonato * sulfonimidoyl* = sulfurimidoyl sulfonio = sulfoniumyl = sulfaniumyl* sulfoniumyl = sulfaniumyl* = sulfonio sulfonodihydrazonoyl* = sulfurodihydrazonoyl sulfonodiimidoyl* = sulfurodiimidoyl sulfonodithioyl* = sulfurodithioyl sulfonohydrazonoyl* = sulfurohydrazonoyl sulfonothioyl* = sulfurothioyl sulfonyl* = sulfuryl sulfonylbis(methylene)* (not sulfonyldimethylene) sulfonylbis(oxy)* (not sulfonyldioxy) HS-CS-S-CS− HS-CO– HS-CO-O– S= S=C= P-73.6 P-63.1.5 P-67.1.4.2.1 P-66.1.5.1.3.3 P-65.2.1.6 en da tio ns H2S+− HS− (HS)BH– HN=C(SH)-NH− HS-CS– sulfaniumyl* = sulfoniumyl = sulfonio sulfanyl* (not mercapto) sulfanylboranyl* (C-sulfanylcarbonimidoyl)amino* sulfanylcarbonothioyl = dithiocarboxy* [(sulfanylcarbonothioyl)sulfanyl]carbonothioyl = [(dithiocarboxy)sulfanyl]carbonothioyl* = [(sulfanylthiocarbonyl)sulfanyl]thiocarbonyl {not [(dithiocarboxy)sulfanyl]thioformyl} sulfanylcarbonyl* (sulfanylcarbonyl)oxy* sulfanylidene* = thioxo sulfanylidenemethylidene* = thioxomethylidene sulfanyloxy* = SO-thiohydroperoxy (no longer mercaptooxy) [(sulfanyloxy)carbonyl]oxy* =[(SO-thiohydroperoxy)carbonyl]oxy DRAFT October 2004 Page 1302 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 29 sulfonyldioxy: see sulfonylbis(oxy)* sulfooxy* sulfuramidoyl = aminosulfonyl = sulfamoyl* sulfurimidoyl = sulfonimidoyl* sulfurochloridoyl = chlorosulfonyl* sulfurochloridoyloxy = (chlorosulfonyl)oxy* sulfurocyanidoyl = cyanosulfonyl* sulfurodihydrazonoyl = sulfonodihydrazonoyl* sulfurodiimidoyl = sulfonodiimidoyl* sulfonodithioyl* = sulfurodithioyl sulfurohydrazonoyl = sulfonohydrazonoyl* sulfuro(isothiocyanatido)thioyl = isothiocyanatosulfonothioyl* sulfuroisothiocyanatidoyl = isocyanatosulfonyl* sulfurothioyl = sulfonothioyl* sulfuryl = sulfonyl* HO-SO2-O– H2N-SO2− –S(O)(=NH)– Cl-SO2– Cl-SO2-O− NC-SO2– –S(=NNH2)2– –S(=NH)2– –S(S)2– –S(O)(=NNH2)– −Te− HTe− Te= HO-TeO− OTe< ion vis Pr o PA C IU Page 1303 of 1306 CO P-63.1.5 P-63.1.5 P-64.6.1 P-65.3.2.1 P-65.3.2.3 P-65.1.7.3.1 NH NH C P-67.1.4.4.1 P-67.1.4.4.1 P-65.3.2.3; P-67.1.4.4.1 P-65.3.2.3 P-65.2.2 P-65.1.7.2.3 P-65.3.2.1 P-65.3.2.3 P-64.6.1 Re al OC terephthalimidoyl = benzene-1,4-dicarboximidoyl* thio: see sulfanediyl* (not sulfenyl) thioacetamido: see ethanethioamido* thioacetyl = ethanethioyl* thioazonoyl = azonothioyl* en da tio ns m co NC-Te− HTeC– HO-TeO2− O2Te< Te= terephthaloyl = benzene-1,4-dicarbonyl* 2-thienyl = thiophene-2-yl* m SCN-S(O)(S)− SCN-SO2− –S(O)(S)– −SO2− tellanediyl* (not telluro) tellanyl* (not hydrotelluro) tellanylidene* = telluroxo tellurino* (preferred when unmodified) tellurinyl* telluro: see tellanediyl* tellurocyanato* telluroformyl = methanetelluroyl* tellurono* (preferred when unmodified) telluronyl* telluroxo = tellanylidene* tetradecanoyl* tetramethylene: see butane-1,4-diyl* tetrasulfanediyl* thallanyl * P-65.3.2.3; P-67.1.4.4.2 P-65.3.2.3 P-67.1.4.4.1 P-67.1.4.4.1 P-67.1.4.4.2 P-67.1.4.4.1 P-67.1.4.4.1 P-67.1.4.4.1 P-65.3.2.3; P-67.1.4.4.1 P-65.3.2.3; P-67.1.4.4.1 C P-65.1.7.2.2 CH3-[CH2]12-CO– P-65.1.7.4.1 –S-S-S-S– H2Tl− P-68.4.1.2 P-68.1.2 S CH3-CO− >NH(S)− DRAFT October 2004 P-29.6 P-65.1.7.2.3 P-67.1.4.1.1 Preferred IUPAC Names Appendix 2, September, 2004 30 P-65.1.7.2.3 P-65.1.7.4.1 Pr o thiophene-2-yl* = 2-thienyl vis ion al Re co m m en da tio ns thiobenzamido: see benzenecarbothioamido* thiobenzoyl = benzenecarbothioyl* C6H5-CS− thiobutyryl = butanethioyl* CH3-CH2-CJH2-CS– thiocarbamoyl: see carbamothioyl* thiocarbonyl = carbonothioyl* −CS− thiocarboxy* (unspecified) H{S/O}C− (thiocarboxy)carbonyl: see 2-thiooxalo* thiochlorosyl* S=Cl– thiocyanato* NCS− thiodimethylene: see sulfanediylbis(methylene)* thioformamido: see methanethioamido* thioformyl = methanethioyl* HCS− OS-thiohydroperoxy = hydroxysulfanyl* HO-S− SO-thiohydroperoxy = sulfanyloxy* HS-O− (OS-thiohydroperoxy)carbonoselenoyl = (hydroxysulfanyl)carbonoselenoyl* HO-S-CSe− (thiohydroperoxy)carbonyl = carbono(thioperoxoyl)* HO-S-CO− or HSO-CO− (OS-thiohydroperoxy)carbonyl = (hydroxysulfanyl)carbonyl* HOS-CO− [(SO-thiohydroperoxy)carbonyl]oxy = [(sulfanyloxy)carbonyl]oxy* HS-O-CO-O− (thiohydroperoxy)phosphoryl = phosphoro(thioperoxoyl)* P(O)(OSH)< or P(O)(SOH)< (SO-thiohydroperoxy)phosphoryl = (sulfanyloxy)phosphoryl* P(O)(O-SH)< (OS-thiohydroperoxy)phosphorothioyl = (hydroxysulfanyl)phosphorothioyl*) (HO-S)P(S)< thionitroso* S=N− thionitrososulfanyl* S=N-SH– thionyl = sulfinyl*= −SO− 1-thiooxalo* (not carboxycarbonothioyl) HOOC-CS– 2-thiooxalo* (not (thiocarboxy)carbonyl H{O/S}C-CO– 1-thiooxalylsulfanyl* = (carboxycarbonothioyl)sulfanyl HO-CO-CS-S− (thioperoxy)phosphoryl = (phosphorothioperoxoyl)* >P(O)(OSH) or >P(O)(SOH) P-67.1.4.5 P-65.2.2 P-65.1.7.2.3 P-63.4.2.2 P-63.4.2.2 P-65.2.1.7 P-65.1.5.3; P-65.2.1.7 P-65.1.5.3 P-65.2.1.7 P-67.1.4.1.1 P-67.1.4.1.1 P-67.1.4.1.1 P-67.1.4.3 P-67.1.4.3 P-65.3.2.3 P-65-2.3.3 P-65.2.3.3 P-65.2.3.3 P-67.1.4.1.1 S P-29.6 H2P(S)− H2{O2S}P− >P(S)– CH3-CH2-CS– P-67.1.4.1.1 P-67.1.4.1.1 P-67.1.4.1.1 P-65.1.7.4.1 H{O/S}S HO2S2− S= S=C= P-65.3.2.1 P-65.3.2.1 P-64.6.1 P-65.2.1.8 IU PA C thiophosphinoyl = phosphinothioyl* thiophosphono* (unspecified) thiophosphoryl = phosphorothioyl* thiopropionyl = propanethioyl* thiosulfeno: see disulfanyl* thiosulfino* (unspecified thiosulfo* (unspecified) thioxo = sulfanylidene* thioxomethylidene = sulfanylidenemethylidene* P-65.2.1.5 P-65.1.5.1; P-65.2.1.6 DRAFT October 2004 Page 1304 of 1306 Preferred IUPAC Names Appendix 2, September, 2004 31 CH3 o-tolyl = 2-methylphenyl* P-29.6 m-tolyl = 3-methylphenyl* p-tolyl = methylphenyl* triazano: see triazan-1-yl* triazan-1-yl* (not triazano) 2-triazeno: see triaz-2-en-1-yl* P-29.6 P-29.6 H2N-NH-NH− triaz-2-en-1-io = traz-2-en-1-ium-1-yl* + NH2-N=NH _ triaz-2-en-1-ium-1-yl* = tria-2-en-1-io + NH2-N=NH _ Pr o P-29.3.2.2; P-68.3.1.4.1 P-73.6 P-73.6 P-32.1.1; P-68.3.1.4.1 P-68.1.2 P-67.1.4.2 P-29.6 P-68.4.1.3 P-68.4.1.2 P-29.3.2.2 P-29.3.2.2 P-68.4.1.3 P-68.4.1.2 P-68.4.1.2 P-68.4.1.3 P-68.4.1.2 HS-CS-CS− (HS)2P(S)HS-S(S)2− (C6H5)3C− P-65.2.3.3 P-67.1.4.1.1 P-65.3.2.1 P-29.6 CH3-[CH2]9-CH2− P-29.3.2.1 co HN=N-NH− H2B=BH-B− (HO)3Si– (C6H5)3C− HOOO− −OOO− (CH3)2SiH− (SiH3-NH)2SiH− HSeSeSe− −SeSeSe− −SSS− HTeTeTe− −TeTeTe− Re al vis ion triaz-2-en-1-yl* (not 2-triazeno) triborane(5)-1-yl* trihydroxysilyl* triphenylmethyl = trityl* trioxidanyl* trioxidanediyl* trisilan-2-yl* trisilazan-3-yl* triselanyl* triselanediyl* trisulfanediyl* (not trithio) tritellanyl* tritellanediyl* trithio: see trisulfanediyl* trithiooxalo* [(not (dithiocarboxy)carbonothioyl] trithiophosphono* trithiosulfo = sulfanylsulfonodithioyl* trityl* = triphenylmethyl m m triaz-2-en-1-ium-1-yl* = triaz-2-en- undecan-1-yl: see indecyl* undecyl* (not undecan-1-yl) en da tio ns PA C ureido: see carbamoylamino* ureylene: see carbonylbis(azanediyl)* vinyl = ethenyl* vinylene: see ethene-1,2-diyl* vinylidene = ethenylidene* CH2=CH− P-32.3 CH2=CH= P-32.3 yloamino* −NH• P-71.5 IU ylocarbonyl* Page 1305 of 1306 • −C=O • DRAFT October 2004 P-71.5 Preferred IUPAC Names Appendix 2, September, 2004 32 −CH2 P-71.5 ylooxy* (not ylohydroxy) (ylooxy)carbonyl* −O• −CO-O• P-71.5 P-71.5 IU PA C Pr o vis ion al Re co m m en da tio ns ylomethyl* DRAFT October 2004 Page 1306 of 1306 [...]... be used either as preferred IUPAC name or as an allowed alternatives in general nomenclature, for example, naphthalene, benzoic acid and pyridine m P-12.4 Methodology Re co In this book, names of parent structures, characteristic groups and their prefixes, and organic compounds are systematically identified as preferred IUPAC names or preselected IUPAC names; preferred IUPAC stereodescriptors are described... preferred IUPAC names it is necessary to be prescriptive about when omission of locants is permissible Thus, in preferred IUPAC names, if any locants are essential for defining the structure, then all locants should be cited For example, the omission of the locant ‘1’ in 2-chloroethanol, while permissible in general usage, is not allowed in the preferred IUPAC name 2-chloroethan-1-ol Also, in preferred IUPAC. .. of substitution or functionalization by carbon-containing groups is assigned a unique 'preselected' name to be used as the basis for deriving a preferred IUPAC name Parent names identified here as 'preselected' may not necessarily emerge as preferred IUPAC names in the context of inorganic chemical nomenclature All names listed in Table 2.1, with the exception of methane (carbane), are preselected names,... general usage, is not allowed in the preferred IUPAC name 2-chloroethan-1-ol Also, in preferred IUPAC multiplicative names and in preferred IUPAC names for ring assemblies locants are always cited, e.g., 1,1′-oxydibenzene and 1,1′-biphenyl Locants are omitted in preferred IUPAC names in the following cases PA C P-14.3.3.1 Terminal locants in names for mono- and dicarboxylic acids derived from acyclic hydrocarbons... N COOH N chlorocoronene (PIN) pyrazinecarboxylic acid (PIN) DRAFT 7 October 2004 Preferred IUPAC Names Chapter 1, September, 2004 29 Examples: decahydronaphthalene (PIN) 3 2 1 CF3-CF2-CH2-OH m CF3-CF2-CF2-COOH en da tio ns P-14.3.3.3 All locants are omitted in compounds in which all substitutable positions are completely substituted or modified in the same way The prefix ‘per-’ is no longer recommended... 1-methyltridecastannane (PIN) IU (CH3-O)3PO tridecastannane (preselected name) (HO)2P(O)-OH trimethyl phosphate (PIN) phosphoric acid (preselected name) DRAFT 7 October 2004 Page 12 of 1306 Preferred IUPAC Names Chapter 1, September, 2004 8 H2Si 5 O O 4 Si 1 CH3 2 Si O3 6 H2Si H 5 O 2 SiH2 en da tio ns 1 6 O 4 Si O3 H2 H2 2-methyl-1,3,5,2,4,6-trioxatrisilinane (PIN) 2-methylcyclotrisiloxane 1,3,5,2,4,6-trioxatrisilinane... above Replacement nomenclature and conjunctive nomenclature also require specific principles, conventions and rules On the contrary, additive and subtractive Page 11 of 1306 DRAFT 7 October 2004 Preferred IUPAC Names Chapter 1, September, 2004 7 Re co m m en da tio ns operations do not correspond to nomenclatures in their own right, but are necessary complements to other nomenclatures It is very important... IUPAC names; preferred IUPAC stereodescriptors are described and used in Chapter 9 To facilitate the construction of the names of organic compounds, preferred prefixes for use in generating preferred IUPAC names are listed in Appendix 2 along with other recommended prefixes to be used in general nomenclature P-13 Operations in nomenclature of organic compounds The substitutive operation The replacement... hydrogen atoms for another atom or group of atoms This process is expressed by a suffix or a prefix denoting the atom or group being introduced Examples: Page 13 of 1306 DRAFT 7 October 2004 Preferred IUPAC Names Chapter 1, September, 2004 9 CH3-CH3 CH3-CH2-SH ethanethiol (PIN) (substitutive suffix = ‘thiol’) en da tio ns ethane (PIN) Br benzene (PIN) bromobenzene (PIN) (substitutive prefix = ‘bromo’)... P-101.4) and must be applied only when specifically prescribed because the nomenclature of organic compounds is normally based on carbon atoms Examples: DRAFT 7 October 2004 Page 14 of 1306 Preferred IUPAC Names Chapter 1, September, 2004 10 7 1 13 BH 4 H 2 CH HB 5 en da tio ns 8 N1 H H H 2 BH 4 21 H 14 BH 5 3 3 1-carba-nido-pentaborane(5) (PIN) (replacement prefix = ‘carba’; carbon replacing boron) ... ‘preferred IUPAC nomenclature’ Any name other than a preferred IUPAC name, as long as it is unambiguous and follows the principles of the IUPAC recommendations herein, is acceptable as a ‘general’ IUPAC. .. seniority, page Complete list of suffixes and functional replacement analogues for IUPAC preferred names, in decreasing order of seniority, page 12 Chapter Constructing preferred IUPAC names 5.1... preferred IUPAC names by functional replacement, page DRAFT October 2004 Page of 1306 Preferred IUPAC names List of tables, September , 2004 4.4 Carboxylic and sulfonic acids suffixes generated for IUPAC