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Home , Azane, Bullvalene, Plumbane, Polysulfane, Sulfanyl

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Index

Page numbers in bold-type refer to the beginning of a section or to the more detailed treatment of an entry. (T) denotes that an entry refers to a table.

'(+)', stereodescriptor 572 'abietane' 522 common or exotic 268 '(–)', stereodescriptor 572 '(4-abu)', ligand-name abbreviation 472(T) of carbohydrates 497 '(±)', stereodescriptor 572 'Ac', ligand-name abbreviation 472(T) seniority 19ff.(T) > sign, definition 2 '(acac)', ligand-name abbreviation 443, 450, 'aci-nitro-' 18(T), 329, 340, 378 sign, definition 2 472(T), 590 'aconitane' 487 ~ sign, definition 2 '(acacen)', ligand-name abbreviation 472(T) 'acridarsine' 91(T) → arrow, definition 2 'ACD' 537 'acridine', exception of numbering 93(T), 'α' 'aceanthrene' 87 112 CA stereodescriptors until 1999 573ff. 'aceanthrylene' 89(T) 'acridophosphine' 91(T) citation in names 572 'acenaphthene' 87 '1H-acrindoline' 94(T) meso ring structures 573 'acenaphth(o)-' 89(T), 102 '' 328 steroids 516, 571 'acenaphthoquinone' 334 'acrylaldehyde' 328 terpenes 520, 571 'acenaphthylene' 89(T) 'acrylamide' 301 'α-carotene' 524 '-acene' 89(T) 'acrylic acid'/ 'acryloyl-' 204 'α-d' 498 'acephenanthrene' 87 'acyl', ligand name 442(T) 'α-l' 498 'acephenanthrylene' 89(T) acyl, definition 2 'α-neuraminic acid' 495 '' 327 acylals 326 α terminus, polymers 532 acetals 23(T), 24(T), 326, 411 '(acylamido)', ligand names 449 'β' of monosaccharides 503 '(acylazanido)', ligand names 449 carotenoids 524 of steroids 518 acyl cation center 176f. CA stereodescriptors until 1999 573ff. '' 299, 300 'acyloin' 335, 337 citation in names 572 '(acetamidine)', ligand name 452 acyl center 163, 164 meso ring structures 573 'acetate' 190, 271, 273 acyl steroids 516, 571 '(acetato-κO)', ligand name 445 at heteroatoms 25(T), 335, 337 terpenes 520, 571 '' 203 general naming 13 'β-alanine'/ 'β-alanyl-' 210, 490 'acetic anhydride' 258 As-acyl substituents 384, 386 'β-carotene' 524 'acetoacetamide' 301 B-acyl substituents 399, 400 'β-d' 498 'acetoacetic acid'/ 'acetoacetyl-' 209 Bi-acyl substituents 392, 393 'β-l' 498 'acetohydrazonic acid' 216 Ge-acyl substituents 404, 406 'β-muramic acid' 495 'acetoin' 336 N-acyl substituents 297, 313, 372 δ convention 4, 597 '' 335 P-acyl substituents 384, 386 'δc ' 597 'acetonedicarboxylic acid' 213 Pb-acyl substituents 404, 406 '∆', stereodescriptor, determination 583 '' 322 Sb-acyl substituents 392, 393 'ε', carotenoids 524 '(acetonitrile)', ligand name 452(T) Si-acyl substituents 404, 406 η descriptor 'acetonyl', radical name 161 Sn-acyl substituents 404, 406 definition 4 'acetonyl-', prefix 335 'adamantane' 118 description of coordination site 438, 440ff. 'acetonylium' 176 'adamantyl-' 120 κ descriptor 'acetophenone' 337 'added ' 547 definition 5 'acetoxy-' 275 'added' indicated H atom 547 description of coordination site 438 'acetoxyl' 165 333 in ligand names with η descriptors 440 'acetyl' addition compounds 'κ', carotenoids 524 halide suffix 285 lit. 536 λ convention 5, 593, 594 ligand name 442(T) molecular 36, 437 'λn ' 594f. radical name 164 additive names 'Λ', stereodescriptor, determination 583 'acetyl-' definition 3 µ descriptor amides 303 monosulfones, monosulfoxides, monosul- definition 6 carboxylic acids 204 fides, and analogs with replace- in bridge-ligand names 454 esters 275 ment names 420 in polyborane names 397 isolated group 156 O-, S-, Se, and Te-substituted S-, Se-, and µ ligands, see bridge ligands ketones 335 Te-heterocycles 416 'ξ' '(acetylacetonato)', ligand name for abbrevia- pseudoketones 338 steroids 516, 571 tion 443, 450, 472(T), 590 additive nomenclature (see also additive terpenes 520, 571 '' 55, 57 names) 36 π complexes, CIP convention 592 'acetylide' 188 '(ade)', ligand-name abbreviation 472(T) π-ligands, see hapto ligands acetylides 458 'adenine' 364, 510, 526 'ϕ', carotenoids 524 achiral core 559 '(adenine)', ligand name for abbreviation 'χ', carotenoids 524 acid azides, seniority 24(T) 472(T) 'ψ' acid halides 285 'adenosine' 510 nucleoside abbreviation 511 boric acids 254 '(adenosine)', ligand name for abbreviation carotenoids 524 boronic and borinic acids 255 472(T) ω terminus, polymers 532 carbohydrate acids 498 '(adenosine monophosphato)', ligand name seniority 24(T) for abbreviation 472(T) silicic acids 253 'adenylic acid' 511 'A', nucleoside abbreviation 510 suffixes 286(T) 'adenylyl-' 512 'A', stereodescriptor, determination 583 acids 'adipamide' 301 'abeo-' 524, 541 'Class-I' or 'Class-II 268 'adipic acid'/ 'adipoyl-' 204 609 Index

'(ado)', ligand-name abbreviation 472(T) 'alloisoleucine'/ 'alloisoleucyl-' 211 amidines 295 '(adp)', ligand-name abbreviation 472(T) 'allophanic acid'/ 'allophanyl-' 231 seniority 24(T) 'adrenaline' 365 'allophanyl-' 305 'amidino-' 233, 298(T), 317 '(aet)', ligand-name abbreviation 472(T) 'allose' 494 '-amidium' (+ E+) 173 affixes 'allothreonine'/ 'allothreonyl' 212, 491 'amido', ligand name 438, 442(T) acid halides (IUPAC) 286(T) 'alloxane' 309 'amido-', affix in S-, Se-, and N-oxoacid boronic and borinic acids 255 'allyl-' 56 names 238 definition 3 'allyl alcohol' 348 '-amid(o)-', infix in P- and As-oxoacid names polynuclear C-oxoacids 232 alphabetical order 53 245 polynuclear P- and As-oxoacids 249 affixes in S-, Se-, and N-oxoacid names 238 '-amido-' 303 polynuclear S- and Se-oxoacids 239 attached-component names 97 'amidogen' 163 S-, Se-, and N-oxoacids 238 bridge-ligand names 454 '-amidogen' 164 S-, Se-, Te-, N-, Si-, and B-oxoacids 21(T) bridge names 124 'amidosulfenyl chloride' 290 silicic acids 253 cation names 220, 234, 249, 279, 456 'amidosulfuric acid' 239 sulfonic acids and analogs (IUPAC) 224 class terms 290 '-amidoxime' 298(T), 302 'agaropectin' 507 higher-order-attached-component names 'amidrazone' 314 'AIBN' 323 106 '-amidrazone' 298(T) 'ajmalan' 487 'hydro-' 36, 541 '-amidyl' 164 '-al' 24(T), 327 in acyl names of acid halides 288, 292 '-amidylium' 177 carotenoids 524 in acyl prefixes aminals 326, 359 '(ala)', ligand-name abbreviation 472(T) of amides 303, 305, 308 '-aminato', ligand name 444 'alaninal' 328 of esters 275, 276, 277, 278 '-' 25(T), 360 'alaninate' 220 of ketones 335 amine oxides 25(T) '(alaninato)', ligand name for abbreviation infixes amine N-oxides 363 472(T) in names 19(T), 214, 359 'β-alanine'/ 'β-alanyl-' 210, 490 216, 218 N-alkylidene-substituted primary 362 'alanine'/ 'alanyl-' 210, 490 in C-oxoacid names 230 primary, secondary, and tertiary 359 '-alaninium' (+ E+) 174 in P- and As-oxoacid names 22(T), 245 seniority 25(T) alcohols 347 in peroxy acid names with suffix 19(T) '-aminium' (+ E+) 173 amino acids 491 in sulfonic acid names and analogs 'amino-' 25(T) 'Class-I' and 'Class-II' 268f. 19(T), 224, 225, 226 amines 360 common and exotic 268f. italic element symbols in ligand names 438 N-heterochains 64 functional-class nomenclature 38 ligand abbreviations in formulas of coor- '-amino-' of peptides 492 dination compounds 472(T) amides 303ff. seniority 25(T) ligand formulas in formulas of coordina- amines 360 Si compounds 404, 406 tion compounds 472(T) S-, Se-, Te-, and N-oxoacids 240 aldaric acids 497 ligand names 456, 458, 461 amino acids 210, 490 '-' 327 ligand names of polynuclear coordination acid halides 287 aldehyde hydrate 349 compounds 464, 465 alcohols 491 aldehyde 325, 330 parent-component letters 103 491 'aldehyde ' 197 parent- names 53 amides 299, 491 aldehyde oximes 325, 329 prefixes 14, 53 anhydrides 491 aldehydes 325 primary-attached-component names 105 esters 271, 491 amino acids 491 substituent prefixes hydrazides 491 of peptides 492 in amine names 360 nonstandard 492 seniority 24(T) in ester names 270, 273 stereodescriptors 571 aldehydic acids 209 in hydrazide names 314 amino acid sequence names 299, 492 'aldehydo' 330 in names 330, 341 aminoaldehyde 327 'aldimine' 368 subtractive prefixes 541 '(aminocarbonyl)-' 20(T), 24(T), 216, 298(T) alditols 497 alphanumerical locants, see locants aminocarboxylic acids, see amino acids aldonic acids 497 alphanumerical order 53 '(aminohydrazonomethyl)-' 298(T) aldose parent names 496 'altro-' 494 '(aminoiminomethyl)-' 298(T) aldoses 496 'altrose' 494 '(aminomalonato)', ligand name for abbre- aldosuloses 496 '(ama)', ligand-name abbreviation 472(T) viation 472(T) 'aldoxime' 331 ambiguities, avoidance by choice of multiply- '(aminooxy)-' 363, 375 alduronic acids 497 ing affixes 539 '(aminoseleninyl)-' 298(T) '-alene' 89(T) 'ambrane' 523 '(aminoseleno)-' 298(T) 'alka-' 55 '-amic acid' 210, 301 '(aminoselenonyl)-' 298(T) alkaloids 487, 518 '-amidato', ligand name 444 '(aminosulfinothioyl)-' and analogs 298(T) '(alkanaminido)', ligand names 449 'amide' 304, 306, 307 '(aminosulfinyl)-' 298(T) 55 '-amide' 24(T), 298(T) '(aminosulfonimidoyl)-' 298(T) 'alkanido', ligand name 442 anion 190 '(aminosulfonohydrazonoyl)-' 298(T) 'alkan(o)-', bridge name 125 '-amide hydrazone' 302 '(aminosulfonothioyl)-' and analogs 298(T) 55 amides 295 '(aminosulfonyl)-' 20(T), 225, 298(T) 'alk[x]en(o)-', bridge name 125 amino acids 491 '(aminotellurinyl)-' 298(T) alkoxycarboxylic acids 208f. boric acids 254 '(aminotelluro)-' 298(T) '', ligand name 442(T) boronic and borinic acids 255 '(aminotelluronyl)-' 298(T) alkyl, definition 2 carbohydrate acids 498 '(aminothio)-' 298(T), 363, 375 '(alkylazanido)', ligand names 449 cyclic 295 '(aminothioxomethyl)-' and analogs 298(T) alkyl halides, functional-class nomenclature primary 297f. '[aminotris(hydroxymethyl)]', ligand 38 replacement names 61 name for abbreviation 484(T) '(alkyloxy)', ligand name 442(T) secondary 299 '[aminotris(methylenephosphonato)]', ligand 55 seniority 24(T) name for abbreviation 472(T) 'alk[x]yn(o)-', bridge name 125 silicic acids 253 'aminoxyl' 163 'allene' 55, 57 suffixes 298(T) 'aminyl' 163 'allo-' 494 tertiary 299 '-aminyl' 164 'allocystathionine' 491 '-amidinato', ligand name 450, 464 '-aminylene' 164 'allo-inositol' 509 '-amidine' 298(T) '-aminylium' 177

610 Index

'-aminyliumyl', radical cation 200 anions 187 'arsenido', ligand name 443(T) 'ammine', ligand name 438, 452(T) seniority 19(T) 'arsenin' 78(T) '' 63 anion substituents, prefixes 193 'arsenite' 243 'ammonio-' 182 'anisaldehyde' 331 'arsenoso-' '' 170 'anisic acid'/ 'anisoyl-' 209 As-oxoacids 247 ligand name 453(T) 'anisidine' 364 esters 277 '-ammonium' (+ E+) 174 'anisole' 412 '(arsenosoamino)-' 308 '(amp)', ligand-name abbreviation 472(T) annulenes 67, 95, 101 'arsenous acid' 243 'amyl-' 59 anomeric center 498 'arsinate' 243 '-an', homoglycans 507 'anthra-' 89(T), 102 '1H-arsindole' 91(T) 'a' names, see replacement names '', exception of numbering 89(T), 'arsindolizine' 91(T), 93(T) 'androstane' 516 112 '' 26(T), 63, 385 '-ane' 'anthranilamide' 301 'arsine imide' 367, 386 carbomonocycles 67 'anthranilic acid' 491 'arsine oxide' 386 Hantzsch–Widman names 78(T) 'anthranilic acid'/ 'anthraniloyl-' 210 'arsine sulfide' and analogs 386 heterochains 61ff. 'anthraquinone' 334 'arsinic acid' 243 heteromonocycles 82 'anthrazine' 94(T) '-arsinic acid' 22(T), 244 chains 55 '-anthrene' 91(T) arsinic acids, seniority 22(T) spiropolycycles 134 'anthrol' 347 'arsinico-' 22(T), 153, 248, 386 von Baeyer bridged polycycles 118 'anthrone' 334 'arsinidene', ligand name 443(T) '([9]aneN3)', ligand-name abbreviation 'anthryl-' 88 'arsinidene-' 472(T), 482(T) 'anthyridine' 93(T) As-heterochains 385 '([12]aneN4)', ligand-name abbreviation 'anti ' As-oxoacids 247, 248 472(T), 474(T) CA stereodescriptors until 1999 573ff. 'arsinidenio-' 182 '([14]aneN4)', ligand-name abbreviation citation in names 572 'arsinidyne-' 472(T), 474(T) von Baeyer bridged polycycles 120, 573 As-heterochains 385 '([18]aneP4O2)', ligand-name abbreviation 'antimonate' 253 As-oxoacids 247 472(T) 'antimonic acid' 253, 395 'arsinimyl-' '([9]aneS3)', ligand-name abbreviation 'antimonous acid' 253 As-heterochains 386 472(T) antimony compounds, see Sb compounds As-oxoacids 247, 248 '([12]aneS4)', ligand-name abbreviation antimony-containing oxoacids, see Sb-oxo- 'arsinimylidene-', As-oxoacids 247, 248 472(T) acids 'arsinite' 244 '([9]aneSN2), ligand-name abbreviation 590 'antimony ion (Sb3–)' 188 'arsino', ligand name 443(T) angular bridgeheads, indicated H atom 549 'apiose' 503 'arsino-' angular center 'apo' names, carotenoids 525 As-heterochains 64, 385 angular heteroatom in peripheral num- Appendix IV 1 As-oxoacids 247, 248 bering of fused polycycles 108 'a' prefixes, see heteroatom syllables 'arsinoline' 91(T) saturated, in cyclic molecular-skeleton 'aqua', ligand name 438, 452(T) '4H-arsinolizine' 91(T), 93(T) parents 97, 547 'aR ' 561 'arsinothioyl-' and analogs 'anhydride' 258 'ar-', locants 50 As-heterochains 386 anhydrides 257 Arabic numerals, locants 49 As-oxoacids 247, 248 amino acids 491 'arabino-' 494 'arsinothioylidene-' and analogs boric acids 254, 259 'arabinose' 494 As-heterochains 386 boronic and borinic acids 255, 259 'arachic acid' 204 As-oxoacids 247, 248 carbohydrate acids 498 'arachidonic acid' 204 'arsinothioylidyne-' and analogs cyclic 23(T), 257 'aracytidine' 505 As-heterochains 386 exception of the seniority 23(T) 'arene' 85 As-oxoacids 247 of three or more different acids 263 'arenido', ligand name 442 'arsinous acid' 244 polynuclear C-oxoacids 232, 259, 262 'areno-', bridge name 128 '-arsinous acid' 22(T), 244 polynuclear P- and As-oxoacids 249, 259, '(arg)', ligand-name abbreviation 472(T) arsinous acids, seniority 22(T) 262 '(argininato)', ligand name for abbreviation 'arsinoyl-' 247 polynuclear S- and Se-oxoacids 239, 259, 472(T) 'arsinyl', ligand name 442(T) 262 'arginine'/ 'arginyl-' 210, 490 'arsinyl-' replacement names 61 '-aric acid' 497 As-heterochains 386 seniority 23(T) aromaticity, transformation convention in As-oxoacids 247, 248 silicic acids 253, 259 the CIP system 562 'arsinylidene-' symmetrical acyclic 258f. arrow names As-heterochains 386 unsymmetrical acyclic 260 oligonucleotides 512 As-oxoacids 247, 248 'anhydride with…' 260 oligosaccharides 505 'arsinylidyne-', As-oxoacids 247 'anhydro-' 38, 541 arrow →, definition 2 'arso-' monosaccharides 503 'arsa-' 543(T) As-heterochains 386 'anhydroselenide' 258 'arsane' 63, 385 As-oxoacids 247 anhydroselenides 257 'arsanilic acid' 491 esters 277 'anhydrosulfide' 258 'arsanthrene' 91(T) '(arsoamino)-' 308 anhydrosulfides 257 'arsanthridine' 91(T) 'arsolene' 77 'anhydrotelluride' 258 'arsenane' 78(T) 'arsonate' 243 anhydrotellurides 257 'arsenate' 243 'arsonic acid' 243 '-anilic acid' 210, 301 'arsenenate' 244 '-arsonic acid' 22(T), 244 '-anilide' 301 'arsenenic acid' 244 arsonic acids, seniority 22(T) anilides 301 arsenenic acids, seniority 22(T) 'arsonio-' 182 'aniline' 360 'arsenenite' 244 'arsonite' 243 'anilino-' 360 'arsenenous acid' 244 'arsonium' 170, 175 anils 362, 368 arsenenous acids, seniority 22(T) 'arsono-' anion center 'arsenic acid' 243 As-heterochains 386 at characteristic group (– H+) 190 arsenic acids, seniority 22(T) As-oxoacids 22(T), 247 at molecular-skeleton parents (– H+) 188 arsenic compounds, see As compounds esters 277 by formal addition of H– 193 arsenic-containing oxoacids, see As-oxoacids prefix 153 by formal removal of H+ 188 'arsenide' 188 '(arsonoamino)-' 308

611 Index

'arsononitridyl-' 'azelaic acid'/ 'azelaoyl-' 204 'benzidino-' 360 As-heterochains 386 'azetine' 77 'benzil' 337 As-oxoacids 247 'azi-', N-heterochains 64, 147, 373 'benzilamide' 301 'arsononitrylidene-', As-oxoacids 247 'azide' 285ff. 'benzilic acid'/ 'benziloyl-' 209 'arsonous acid' 243 anion 237 'benzimidazo-' 103 '-arsonous acid' 22(T), 244 azides, see acid halides 'benzimidic acid' 216 arsonous acids, seniority 22(T) 'azido', ligand name 438, 443(T) 'benzindene' 99, 425 'arsonoyl-' 248 'azido-' 18(T), 288, 292, 378 'benzisoxazole' and analogs 97 'arsorane' 26(T), 63, 385 affix in S-, Se-, and N-oxoacid names 238 'benz(o)-' 102, 541 'arsoranyl-', As-heterochains 385 '-azid(o)-', infix in names 'benzoate' 190, 271 'arsoroso-', As-heterochains 386 of C-oxoacids 229 '(benzo-15-crown-5)', ligand-name abbrevia- 'arsoryl-' 248 of P- and As-oxoacids 245 tion 472(T) 'aryl', ligand name 442(T) 'azidothymidine' 382 'benzofuran' 97 'aryl-' 85 'azimino-', bridge name 126(T) 'benzofuro-' and chalcogen analogs 102 aryl, definition 2 azines 23(T), 24(T), 325, 330, 333, 341 benzoheteromonocycle 96 As compounds 383 'azinic acid' 238, 329, 340, 379 'benzoic acid' 205 seniority 26(T) 'azino-' 'benzoin' 338 As-heterochains 384 bridge name 126(T) '' 322 As-heterocycles 383 hydrazides 315 'benzophenone' 337 As-oxoacids 243 hydrazones 330, 341 benzo primary attached component 96 salts 243, 249 multivalent substituent 34(T) '1H-2-benzopyran' 92(T) seniority 22(T) N-heterochains 64, 147, 373 '2H-1-benzopyran' 92(T) 'aS ' 561 'azinoyl-' 238, 363 'benzoquinone' 334 'ascorbic acid' 495, 527 'azo-' 'benzoquinone diimine' 368 '(asn)', ligand-name abbreviation 472(T) bridge name 126(T) 'benzoquinone monoimine' 369 '(asp)', ligand-name abbreviation 472(T) hydrazides 315 'benzothiophene' and chalcogen analogs 96 'asparaginate' 221 hydrazones 330, 341 'benzotrichloride' 431 '(asparaginato)', ligand name for abbrevia- multivalent substituent 34(T) 'benzoxazole' and chalcogen analogs 97 tion 472(T) N-heterochains 64, 147, 373 'benzoyl' 'asparagine' 299 'azobenzene' 373 halide suffix 285 'asparagine'/ 'asparaginyl-' 210, 490 '2,2ʹ-azobis[isobutyronitrile]' 323 ligand name 442(T) 'aspart-1-al' 328 azo compounds 372 'benzoyl-' 'aspartate' 221 'azodicarboxylic acid' 207 amides 303 '(aspartato)', ligand name for abbreviation 'azomethine imine' 195 carboxylic acids 205 472(T) azomethines 362, 368 esters 275 'aspartic acid'/ 'aspartoyl-'/ 'aspartyl-' 210, 490 'azomethine ylide' 197 isolated group 157 'aspartyl-' 492 'azonaphthalene' 373 ketones 335 'aspidospermidine' 487 'azonia-' 541, 543(T) '(benzoylacetonato)', ligand name for abbre- assignment rules 560 'azonic acid' 238 viation 474(T) 'astata-' 543(T) 'azono-' 238 'benzyl', radical name 161 'astato', ligand name 442(T) 'azonoyl-' 238 'benzyl-' 69, 153 'astato-' 18(T), 429 'azoxy-' 339 'benzyl alcohol' 348 'astatyl-' 18(T), 429 multivalent substituent 34(T) 'benzylamine' 360 'a' syllables, see heteroatom syllables N-heterochains 374 'benzylidene-' 69 'asymmetric atom', see chirality center 'azoxybenzene' 339, 374 'benzylidyne-' 71, 153 '-ate' azoxy compounds 374 'benzyne' 70 acid anion (salt) 19(T), 190, 220, 227, 234, 'AZT' 382 'betaine' 197 249 'azulene' 89(T) Bi compounds 391, 458 central-atom names 461, 464, 465f., 543(T) seniority 26(T) esters 23(T), 270, 273, 279 Bi-heterochains 392 'atisane' 523 B compounds 397 Bi-oxoacids 253 '(atmp)', ligand-name abbreviation 472(T) lit. 536 seniority 23(T) '-ato', ligand names 442, 444 seniority 27(T) 'bi-' 141, 539 '-ato-', anion (prefix) 193 B-heterocycles 391, 398 'biacetyl' 335 atomic numbers 543(T) B-oxoacids 253 'bicyclo-' 117, 541 sequence rules 566 seniority 23(T) '(big)', ligand-name abbreviation 474(T) zero, for dummy atoms in the CIP system 'barbituric acid' 309 'biguanide' 305 562 'barium salt (1:1)' 233 '(biguanid-3-ido)', ligand name for abbrevia- '(atp)', ligand-name abbreviation 472(T) base component, see parent component tion 474(T) 'atropic acid'/ 'atropoyl-' 204 Baughton system 599, 601 'biguanidine' 304 attached component '(2,3-bdta)', ligand-name abbreviation '(biim)', ligand-name abbreviation 474(T) at another attached component and at a 472(T) '(2,2ʹ-biimidazolato)', ligand name for abbre- parent component 95, 114 'benzal chloride' 431 viation 474(T) benzoheteromonocycle 96 'benzaldehyde' 327 '-biimine' 124 central 105 'benzaldoxime' 329 'biimino-', bridge name 124, 126(T) definition 3 'benzamide' 299, 300 bile pigments 529 multiple occurrence 101, 105 'benzedrine' 364 'bimetallocene' 460 names 101ff. '' 67 'bimol. monoanhydride' 259 primary, fusion side 103 'benzeneazoethene' 373 '(binap)', ligand-name abbreviation 474(T), senior (choice) 101 'benzenediazohydroxide' 375 590 attached-component locants 103 'benzenethiolate' 191 'biotin' 526 'AutoNom' 537 'benzenetrithiosulfonic acid' 224 'biphenyl' 141 axial chirality, see chirality axis, stereogenic 'benzenetriyl-' 149 '[1,1ʹ-biphenyl]-4,4ʹ-diyl-', multivalent axis 'benzen(o)-', bridge name 125, 126(T), 541 substituent 34(T) 'aza-' 541, 543(T) 'benzhydrol' 351 'biphenylene' 89(T) '', parent name 360, 368 'benzhydryl-' 69 'bis-' 539 '(azanolato)', ligand names 450 'benzhydryl alcohol' 351 '[bis(acetylacetonato)ethylenediamine]', ligand 'azaphospholine' 77 'benzidine' 360 name for abbreviation 472(T)

612 Index

'[1,2-bis(diethylphosphino)]', ligand '-borinic acid' 23(T) '-butoxy-', esters 275 name for abbreviation 476(T) borinic acids '(sec-butyl)-' 57 '(1,2-[bis(dimethylphosphino)ethane]', ligand anhydrides 259 '(tert-butyl)-' 57 name for abbreviation 476(T) B compounds 400 'butyl alcohol' 348 '[bis(dimethylphosphino)methane]', ligand B-oxoacids 254 'tert-butyl peroxide' 410 name for abbreviation 476(T) formal acid halides 292 'butyramide' 301 '[1,2-bis(diphenylphosphino)ethane]', ligand formal amides 308 'butyric acid'/ 'butyryl-' 204 name for abbreviation 476(T) hydrazides 318 'γ-butyrolactone' 268 '[bis(diphenylphosphino)methane]', ligand seniority 23(T) 'Bz', ligand-name abbreviation 474(T) name for abbreviation 476(T) 'bornane' 520 '(bzac)', ligand-name abbreviation 474(T) '[1,3-bis(diphenylphosphino)]', ligand 'bornene' 521 '(bzim)', ligand-name abbreviation 474(T) name for abbreviation 476(T) 'borneol' 351 '(bztz)', ligand-name abbreviation 474(T) 'bisma-' 543(T) 'boronate' 255 'bismuthane' 63, 392 boron compounds, see B compounds 'bismuthate' 253 boron-containing oxoacids, see B-oxoacids 'c', stereodescriptor 573 bismuth compounds, see Bi compounds 'boronic acid' 254 'C ', nucleoside abbreviation 511 bismuth-containing oxoacids, see Bi-oxo- '-boronic acid' 23(T) 'C ', stereodescriptor, determination 583 acids boronic acids ' 13C ' 599(T) '' 26(T), 63, 392 anhydrides 259 C compounds 425 'bismuthine imide' 367, 393 B compounds 400 seniority 27(T) 'bismuthine oxide' 393 B-oxoacids 254 C-oxoacids 229 'bismuthine sulfide' and analogs 393 formal acid halides 292 salts 233 'bismuthino', ligand name 443(T) formal amides 308 seniority 21(T) 'bismuthino-' 64, 392 hydrazides 318 CA 1 'bismuthonia-' 543(T) seniority 23(T) Internet 537 'bismuthonio-' 182 'borono-' 23(T), 153, 400 nomenclature guidelines 1 'bismuthonium' 170 'boroxin' 75 stereodescriptors until 1999 573ff. 'bismuthylene', ligand name 443(T) 'borthiin' 75 'cadaverine' 364 'bismuthylene-' 392 'boryl-' 400 Cahn–Ingold–Prelog system, see CIP system 'bismuthylidyne-' 392 'borylene-' 400 Cahn's example 566 '[bis(salicylidene)diethylenetriaminato]', bridge name 126(T) 'calciocene' 460 ligand name for abbreviation 'borylidyne-' 400 'calciol' 527 482(T) bridge name 126(T) 'caldine' 364 '[bis(salicylidene)ethylenediaminato]', '(bpy)', ligand-name abbreviation 474(T) 'camphanic acid'/ 'camphanoyl-' 208 ligand name for abbreviation '(4,4ʹ-bpy)', ligand-name abbreviation 474(T) 'camphene' 521 482(T), 588 'bradykinin' 493 'camphor' 521 '[bis(salicylidene)propylenediaminato]', branched polyphenyls 'camphoric acid'/ 'camphoroyl-' 205 ligand name for abbreviation ring-assembly substituents 152 CA names (see also index names), definition 3 482(T) bridged fused polycycles 95, 123 'capric acid' 204 '[bis(salicylidene)trimethylenediaminato]', charged, indicated H atom 551 'caproic acid' 204 ligand name for abbreviation indicated H atom 548ff. 'caprylic acid' 204 482(T) saturated or partially saturated 128 'carane' 520 '[bis(thiosalicylidene)ethylenediaminato]', bridged fused-polycycle substituents, pre- 'carba-' 397, 543(T) ligand name for abbreviation fixes 128, 149, 150 'carbadiazone' 316, 326, 374 484(T) bridge ligands 453, 463, 465, 467 '-carbaldehyde' 24(T), 327 'bisulfite' addition compounds, lit. 536 bridge names 125ff.,126 (T) 'carbamate' 190, 234, 271 'biuret' 305 bridges 'carbamic acid' 21(T), 230 block polymers 534 bridged fused polycycles 123 'carbamimidoyl-' 233 'Blue Book' 1, 3 choice (seniority) for bridged fused poly- 'carbamoyl-' 24(T), 157, 233, 298(T) '(bn)', ligand-name abbreviation 474(T) cycles 124 '(carbamoyloxy)-' 276 boldface printing, in names 2 choice (seniority) for von Baeyer bridged 'carbazic acid'/ 'carbazoyl-' 206, 230, 316 bond descriptor in coordination names 463, polycycles 119 'carbazide' 231, 316, 326 464, 466f. dependent 124 'carbazimidoyl-' 235 bonding number 3, 543(T), 593, 594, 597 independent 124 'carbazinic acid'/ 'carbazoyl-' 206, 230, 316 'bora-' 543(T) von Baeyer bridged polycycles 118 '9H-carbazole', exception of numbering '' 400 'broma-' 543(T) 93(T), 112 'borane(1)' 161 'bromide' 285ff. 'carbazone' 316, 326 'borane(2)' 161, 400 bromides, see acid halides 'carbazono-' 305, 316 259, 400 'bromo', ligand name 442(T) 'carbazoyl-' 233, 315 'boranthrene' 91(T) 'bromo-' 18(T), 288, 292, 429 'carbene' 161 'boranyl-' 400 '(bromoformyl)-' 288 '-carbenium' 176 'borate' 254 'bromonio-' 182 carbinol 347 '[borato(1–)]', ligand name 444 'bromonium' 170 carbocycles 425 'borazine' 75 'Bu', ligand-name abbreviation 474(T) hydrocarbon-substituted 426 'boric acid' 254, 400 'bufalone' 518 'carbodiazone' 316, 326, 374 boric acids bufanolides 516 '' 368 anhydrides 259 'bullvalene' 121 24(T), 25(T), 362, 368 B-oxoacids 254 'buta-' 540(T) '-carbodithioic acid' 20(T), 214 formal acid halides 292 'butan(o)-', bridge name 126(T) carbohydrate acids 495, 497 formal amides 308 'but[2]en(o)-', bridge name 126(T) carbohydrates 494 formal cyclic esters 271, 273 'butoxide' 191 oligonucleotides 513 formal hydrazides 318 'butoxy', radical name 165 stereodescriptors 571 salts 254 '(sec-butoxy)-', ethers 412 'carbohydrazide' 231, 316, 326 seniority 23(T) '(tert-butoxy)-', ethers 412 '-carbohydrazide' 314 'borin' 78(T) 'butoxy-' 18(T) '-carbohydrazonamide' 298(T) 'borinane' 78(T) alcohols 351 'carbohydrazone' 326 'borinate' 255 esters 277 carbohydrazones 24(T) 'borinic acid' 255 ethers 412 '-carbohydrazonic acid' 20(T), 216

613 Index

carbohydrazonic acids 216 '-carbothioyl' and analogs, acid halide suf- nonsenior 465 '-carbohydrazonoyl', acid halide suffix 286(T) fixes 286(T) seniority 435 '-carbohydrazonoyl-', acyl prefix 217 '-carbothioyl-' and analogs, acyl prefix 217 central-atom links 463 carbohydroxamic acids 216 '-carboxaldehydato', ligand name 444 central-atom names 543(T) carbohydroximic acids 216 '-carboxaldehyde' 24(T), 327 coordination compounds '-carbohydroximoyl-', acyl prefix 217 '-carboxamide' 24(T), 298(T) anionic 461 '-carbolactone' 268 '-carboxamidine' 298(T) cationic 456 'carboline' 93(T) '-carboxamido-' 303 neutral 458 carbomonocycles 67 '-carboxamidoxime' 298(T) polynuclear 464, 465f. hydrocarbon-substituted 69 '-carboxamidrazone' 298(T) centrality 32, 47 terpenes 67 '-carboximidamide' 298(T) 'cephalotaxine' 489 unsubstituted 67 '-carboximidic acid' 20(T), 216 'cevane' 488, 518 carbomonocycle substituents, prefixes 67, 148 carboximidic acids 216 'C-glycosides' 504 'carbonate' 190, 234, 271 '-carboximidoperoxoic acid' 219 'chalcone' 337 '[carbonato(2–)]', ligand name 445(T) '-carboximidoyl', acid halide suffix 286(T) characteristic group carbon compounds, see C compounds '-carboximidoyl-', acyl prefix 217 definition 3 carbon-containing oxoacids, see C-oxoacids 'carboxy', radical name 163 ending or prefix 19 (T) 'carbonic acid' 21(T), 229 'carboxy-' 20(T), 153, 156 general naming 13 carbonic acids 229 carboxylic acids 203, 205 charged bridged fused polycycles, indicated seniority 21(T) '-carboxy-' 601, 606 H atom 551 'carbonic dihalide' 230 '(carboxyamino)-' 305 charge number 'carbonic dihydrazide' 231 '-carboxylate' definition 4 'carbonimidic acid' 21(T) anion 190, 220 for ligands with noncoordinating acid 'carbonimidoyl-' esters 23(T), 270, 273, 279 functions 444 isolated group 157, 217, 233, 360, 368 '(carboxylato)', ligand name 444 global charge in coordination compounds isolated multivalent substituent 34(T) 'carboxylato-', prefix 220 434, 436 '-carbonitrile' 24(T), 322 '-carboxylic acid' 20(T), 205 in ligand names 'carbonium' 170 alkaloids 489 of 'ato' and 'ito' ligands 444 'carbonochloridic acid' 21(T), 231 '-carboxylic acid anhydride' 23(T) of cationic ligands 453 'carbonohydrazide' 231, 316, 326 '-carboxylic acid ester' 23(T) in names of coordination compounds 'carbonohydrazonoyl-', isolated group 157, '-carboxylic acid hydrazide' 24(T), 314 anionic 461 217, 233, 368 carboxylic acids cationic 456 'carbonoperoxoic acid' 21(T), 230 acyclic 203 polynuclear 464, 465f. 'carbonothioyl', ligand name 438, 452(T) at heterochains 205 chelate ligands 438 'carbonothioyl-' and analogs cyclic 203, 205 Chemical Abstracts Service, see CA isolated group 157, 217, 233, 337 salts 220 'Chemical Substance Index' 1 isolated multivalent substituents 34(T) seniority 20(T) chiral 558 'carbonyl', ligand name 438, 452(T) trivial names 204 chirality axis 'carbonyl-' carboxylic acids and analogs 203 assignment of configuration 560f. isolated group 157, 233, 337 '(carboxyoxy)-' 276 definition 559 isolated multivalent substituent 34(T) 'carbyne' 161 sequence rules 567 '-carbonyl' cardanolides 516 stereodescriptors 'aR ' or 'aS ' 561 acid halide suffix 286(T) 'cardinane' 522 chirality center radical name 164 'carene' 521 assignment of configuration 560 '-carbonyl-' 'carnosine' 491 definition 559 acid halides 288 'α-carotene' 524 sequence rules 566 amides 303, 305 'β-carotene' 524 chirality plane carboxylic acids 205 carotenes 524 assignment of configuration 560f. C-oxoacids 233 carotenoids 524 definition 559 esters 274, 276, 278 'carvacrol' 347 sequence rules 567 ketones 335 'carvacryl-' 70 stereodescriptors 'pR ' or 'pS ' 561 parent-substituent name 157 '(cat)', ligand-name abbreviation 474(T) chirality rule 560 '-carbonyl-' 601, 606 'catechol' 348 chirality sense, see configuration '[carbonylbis(oxy)]-', multivalent substitu- '(catecholato)', ligand name for abbreviation chirality symbol ent 34(T) 474(T) '∆' or 'Λ', determination 583 carbonyl-containing substituents and ana- catena compounds, lit. 536 citation in names 585 logs, prefixes 156 cation center coordination compounds 470, 582 '-carbonyl halide' 24(T), 286(T) at characteristic group (+ E+) 173 coordination polyhedron with the coordi- 'carbonyl imine' 197 at characteristic group (– H–) 176 nation number 7, 8, or 9 591 carbonyls 434 at molecular-skeleton parents (+ E+) 169 'C ' or 'A', determination 583 'carbonyl ylide' 197 at molecular-skeleton parents (– H–) 175 definition 4 '-carboperoxoic acid' 19(T), 218 at O atom or chalcogen analogs (– H–) 177 octahedral coordination polyhedron 588 carboperoxoic acids and analogs 218 by formal addition of E+ 169 'R ' or 'S ', stereogenic central atom, deter- '-carboperoxothioic acid' 218 by formal removal of H– 175 mination 583 carbopolycycles (see also carbocycles), by ring formation 179 square-planar coordination polyhedron 585 terpenes 117 by skeletal bonding of a heteroatom 178 square-pyramidal coordination polyhe- '-carboselenaldehyde' 327 in spiropolycycles 180f. dron 587 '-carboselenoaldehyde' 24(T), 327 cations 169 tetrahedral coordination polyhedron 585 '-carboselenothioic acid' 214 seniority 19(T) trigonal-bipyramidal coordination poly- 'carbostyryl' 296, 334 cation substituents, prefixes 182 hedron 586 '-carbotelluraldehyde' 327 '(cbdca)', ligand-name abbreviation 474(T) trigonal-prismatic coordination polyhe- '-carbotelluroaldehyde' 25(T), 327 '(cdta)', ligand-name abbreviation 474(T) dron 590 '-carbothialdehyde' 327 'cedrane' 522 'chiro-inositol' 509 '-carbothioaldehyde' 24(T), 327 'cellotriose' 505 'chlora-' 543(T) '-carbothioamide' and analogs 298(T) 'cellulose' 507 '(chloramido)', ligand name 443(T) '-carbothioic acid' 20(T), 214 central atom 'chlorane' 429 carbothioic acids and analogs 214 definition 3 'chlorate' and analogs 237 '-carbo(thioperoxoic) acid' 218 multiplying affixes 539 'chloric acid' and analogs 237

614 Index

'chloride' 285ff. '(cit)', ligand-name abbreviation 474(T) cations 169ff. anion 237 'citraconic acid'/ 'citraconoyl-' 204 choice (seniority) 13, 19(T) chlorides, see acid halides 'citral' 331, 521 collection 159ff. 'chlorido', ligand name 442 'citramide' 301 coordination compounds 433ff. '-chlorid(o)-' and analogs, infixes in names 'citrate' 192 esters 267ff. of C-oxoacid 229 '(citrato)', ligand name for abbreviation halogen compounds 429ff. of P- and As-oxoacids 245 474(T) hydrazides 313ff. 'chlorite' and analogs 237 'citric acid'/ 'citroyl-' 209 hydroperoxides 355ff. 'chloro', ligand name 438, 442(T) 'citronellol' 521 367ff. 'chloro-' 18(T), 288, 292, 429 ' 37Cl ' 599(T) ketones 333ff. 'chloro-' and analogs, affixes in S-, Se-, and 'Class-I' acids 268 N compounds 371ff. N-oxoacid names 238 'Class-I' alcohols and thiols 268f. N-oxoacids 237ff. 'chlorocarbonic acid' 231 'Class-II' acids 268 321ff. 'chloroform' 430 'Class-II' alcohols and chalcogen analogs 268 O compounds 409ff. 'chloroformate' 273 class names organometallic compounds 433ff. 'chloroformic acid' 231 definition 4 P compounds 383ff. '(chloroformyl)-' 233 for identical structure units, multiplicative P-oxoacids 243ff. 'chloronio-' 182 nomenclature 32 phenols 347ff. 'chloronium' 170 functional-class nomenclature 39 radical ions 199ff. 'chlorosyl-' 18(T), 429 general naming 13 radicals 161ff. 'chlorous acid' and analogs 237 hydroperoxides 355 S, Se, and Te compounds 415ff. 'chloryl-' 18(T), 429 not conjunctive nomenclature 30 S-, Se-, and Te-oxoacids 237ff. '(C5H4Me)', ligand-name abbreviation 474(T) peroxides 410 Sb and Bi compounds 391ff. choice (see also seniority) polyoxides 410 Sb- and Bi-oxoacids 253ff. bridges polysulfides and analogs 417 Si, Ge, Sn, and Pb compounds 403ff. of bridged fused polycycles 124 polysulfones and analogs 416 Si-oxoacids 253ff. of von Baeyer bridged polycycles 119 polysulfoxides and analogs 416 sulfonic acids and analogs 223ff. main ring of von Baeyer bridged poly- class term zwitterions 195ff. cycles 119 acid halides 289, 290 compulsory numbering 50 molecular-skeleton parents 41 amides 304, 306, 307 computer numbering in von Baeyer bridged poly- definition 4 nomenclature software 1, 537 cycles 119 hydrazides 316, 317 software POLCYC for von Baeyer orientation and/or numbering of fused 'cluster' 467 bridged-polycycle names 117 polycycles 109 cluster compounds 467 'conanine' 518 parent cation 185 cluster compounds, lit. 536 concatenation 153 parent component for fusion names '(C5Me5)', ligand-name abbreviation 474(T) configuration 89(T), 91(T), 98 'cobamic acid' 527 absolute 571 parent radical 167 'cobamide' 527 of steroids 516 parent structures 41 'cobamin' 527 of terpenes 520 parent substituent 154 'cobinamide' 527 stereodescriptors 571 principal group 13, 19(T) 'cobinic acid' 527 carbohydrates 498 senior attached component 101 'cobyrinamide' 527 chirality axis 560 senior compound class 13, 19(T) 'cobyrinic acid' 527 chirality center 560 'cholane' 516 'cobyrinol' 527 chirality plane 560 'cholanthrene' 87 '(cod)', ligand-name abbreviation 474(T) coordination compounds 582ff. 'cholecalciferol' 527 'codeine' 489 of anomeric center of hemiacetal 498 'cholestane' 516 'coenzyme A' 512 organometallic compounds 582ff. 'choline' 174 'colamine' 362 partially known 572 'chromane' 87 colons relative 571 'chromene' 92(T) in ligand names stereodescriptors 571 'chromenone' 334 of bridge ligands 454 specification 559 'chromenylium' 179 with η descriptors 440 stereogenic axis 560 'chrysene' 89(T) with κ descriptors 438 stereogenic center 560 '(chxn)', ligand-name abbreviation 474(T), in sets of locants 49 configurational isomers 557 476(T) common acids 268 configuration descriptors 557 'cinchonan' 488 common alcohols and thiols 268f. configuration number 'cinnamaldehyde' 328 composite prefixes citation in names 585 'cinnamamide' 301 definition 4 coordination compounds 470, 582 'cinnamic acid'/ 'cinnamoyl-' 204 formation 153 definition 4 'cinnamyl-' 69 composite substituents of coordination polyhedron 'cinnamyl alcohol' 351 addition of components 153 octahedral 587 'cinnamylidene-' 69 general naming 153 square-planar 585 'cinnoline' 93(T) substitution of a parent substituent 153 square-pyramidal 587 CIP convention, π complexes 592 compound classes tetrahedral 585 CIP system 3, 559 acid halides 285ff. trigonal-bipyramidal 586 coordination compounds 470 alcohols 347ff. trigonal-prismatic 590 extended tetrahedron, obsolete 561 aldehydes 325ff. with the coordination number 7, 8, or 9 organometallic and coordination com- amides 295ff. 591 pounds 582ff. amines 359ff. conformers 557 pilot atom, obsolete 561 anhydrides 257ff. conjunctive names 'cis' anions 187ff. acid halides 285 by IUPAC 573 As compounds 383ff. alcohols 347 CA stereodescriptors until 1999 573ff. As-oxoacids 243ff. aldehydes 326 citation in names 572 B compounds 397ff. amines 359 monocycles and ring assemblies 573 B-oxoacids 253ff. carboxamides 295 'cis-inositol' 509 C compounds 425ff. carboxylic acids and analogs 203 'cisoid ', stereodescriptor 573 C-oxoacids 229ff. definition 4 'cis' senior to 'trans', CIP system 566 carboxylic acids and analogs 203ff. imines 367

615 Index

conjunctive names (cont.) '-cyanatid(o)-' and analogs, infixes in P- and 'd ' 599(T) multiplying affixes 539 As-oxoacid names 245 stereodescriptor, obsolete 572 nitriles 322 '(cyanato-κN)', ligand name 443(T) 'd' not for '(cyanato-κO)', ligand name 443(T) amino acids 210, 490, 571 carbamic acids 229 'cyanato-' 321(T) carbohydrates 494, 571 ketones 333 acid halides 288 cyclitols 509 P- and As-oxoacids 243 affix in S-, Se-, and N-oxoacid names 238 peptides 571 Si- and B-oxoacids 253 amides 305 ' D' 599(T) sulfamic acids 239 C-oxoacids 233 '(dabco)', ligand-name abbreviation 474(T) sulfonamides and analogs 295 esters 276 '(dach)', ligand-name abbreviation 474(T), sulfonic acids and analogs 223 P- and As-oxoacids 248 476(T) conjunctive nomenclature (see also conjunc- S-, Se-, and Te-oxoacids 240 'DBA' 343 tive names) 30 'cyanic acid' 21(T), 230 '(dbm)', ligand-name abbreviation 476(T) determination of molecular-skeleton anhydrides 321 'DCC' 363 parents 41, 42, 46 formal acid halides 289 'DDQ' 30 general naming 14 formal anhydrides 260, 262, 287 'de-' 38 constitutional isomers 557 'cyanide' 285ff., 322 alkaloids 489 contraction names '-idone' and '-olone' 295, cyanides '(dea)', ligand-name abbreviation 476(T) 334 functional-class names 38, 321(T) 'deca-' 540(T) coordination compounds 433 see acid halides 'decalin' 87, 576 anionic 461 see nitriles 'decalinone' 342 central-atom names 436 'cyanido', ligand name 442 'decalone' 342 seniority 19(T) '-cyanid(o)-', infix in P- and As-oxoacid 'deci-' 539 cationic 456 names 245 definitions 3 central-atom names 436 '(cyano-κC)', ligand name 443(T) 'dehydro-' 37 seniority 19(T) '(cyano-κN)', ligand name 443(T) alkaloids 489 central-atom names 543(T) 'cyano-' 24(T), 288, 292, 321(T), 322 carotenoids 524 mononuclear 433 affix in S-, Se-, and N-oxoacid names 238 standard valences 597 neutral 458 '-cyano-' 601, 605 delta convention, see δ convention central-atom names 436 'cyanocob(III)alamin' 527 dendrimers 32 seniority 19(T) 'cyanoformaldehyde' 322 'deoxy-' 541 polymers 467, 531 '' 163, 322 monosaccharides 503 polynuclear 433, 463ff. cyanogen halides 289 nucleosides 510, 512 seniority 27(T), 434 'cyanyl' 163 '-deoxyribonucleic acid' 514 stereodescriptors 470, 582 '(cyclam)', ligand-name abbreviation 472(T), '(depe)', ligand-name abbreviation 476(T) coordination names 474(T) 'de(phosphinicooxy)-' 513 halogen compounds 18(T), 429 '(cyclen)', ligand-name abbreviation 472(T), 'di-' 540(T) inorganic acids 237, 244 474(T) 'diacetamide' 301 IUPAC variants 433 cyclitols 509 dialdoses 496 coordination number 582(T) 'cyclo' 467 'dianhydride with…' 260, 262 definition 4, 433 'cyclo-' '(diars)', ligand-name abbreviation 476(T) coordination polyhedron 470, 582 alkaloids 489 diastereoisomers 558, 559, 560, 582 coordination site 438ff. carbomonocycles 67 'diazene' 26(T) coordination valence 433 nondetachable name part 541 'diazene oxide' 330, 341 'coronene' 90(T) peptides 492 'diazeno-' 373 'corrin' 527 steroids 517 'diazenyl', ligand name 443(T) '(cot)', ligand-name abbreviation 474(T) triterpenes 523 'diazenyl-' 153, 373 'coumarin' 268, 334 'cycloalk(a)-', attached-component name 'diazo-' 18(T), 378 'Cp', ligand-name abbreviation 474(T) 103 '-diazoate' 375 'Cp* ', not ligand-name abbreviation 474(T) 'endo-cycloalk(a)-', bridge name 125 'diazonio-' 182 '(cptn)', ligand-name abbreviation 474(T) 67 '-diazonium' 177 'creatine' 491 '-', fusion names 101 diazonium cations 175 'cresol' 347 67 'diazophenone' 379 'crotonic acid'/ 'crotonoyl-' 204 cycloalkynes 67 '(dibenzoylmethanato)', ligand name for 'crotyl alcohol' 351 'cyclo-' names 79, 83f. abbreviation 476(T) '(18-crown-6)', ligand-name abbreviation 'endo-cyclopent(a)-', bridge name 126(T) 'dibenzylideneacetone' 343 474(T) 'cyclopenta[a]phenanthrene', steroid num- 'dibismuthine' 26(T) '(crypt-211)', ligand-name abbreviation bering 112 '(2)' 398 474(T) cyclophanes 117, 123 'diborane(4)' 254 '(crypt-222)', ligand-name abbreviation cyclosteroids 517 'diborane(6)' 398 474(T) 'cymene' 69 'di(tert-butyl)carbodiimide' 365 '(cryptand 211)', ligand name for abbrevia- '(cys)', ligand-name abbreviation 474(T) '(dicarbonate)' 234 tion 474(T) 'cystathionine' 212, 491 'dicarbonic acid' 21(T), 232 '(cryptand 222)', ligand name for abbrevia- '(cysteinato)', ligand name for abbreviation '-dicarboximide' 296 tion 474(T) 474(T) '-dicarboxylic acid' 205 C terminus, peptides 492 'cysteine' 571 dicarboxylic acids 203 'cubane' 118 'cysteine'/ 'cysteinyl-' 210, 490 'dicta-' 540(T) 'cumene' 69 'cystine' 571 'dicyclohexylcarbodiimide' 363 'cumene hydroperoxide' 357 'cystine'/ 'cystyl-' 210, 490 '(dien)', ligand-name abbreviation 476(T), 'cumenyl-' 70 '(cyt)', ligand-name abbreviation 474(T) 588 cumulative double bonds 'cytidine' 511 '-diene' nonstandard valences 596 'cytidylic acid' 511 carbomonocycles 67 standard valences 597 'cytidylyl-' 512 heterochains 61ff. 'cumyl-' 70 'cytosine' 309, 510 heteromonocycles 82 'curan' 488 '(cytosine)', ligand name for abbreviation hydrocarbon chains 55 'Cy', ligand-name abbreviation 474(T) 474(T) monosaccharides 503 '' 231, 304, 321 polymers 531 cyanates, functional-class names 38, 321(T) spiropolycycles 134

616 Index

steroids 517 'distibine' 26(T) duplicate atoms 562, 584 subtractive nomenclature 37 'disulfane' 355, 416 dyes, lit. 536 von Baeyer bridged polycycles 118 '(disulfate)' 239 '([14]1,3-dieneN4)', ligand-name abbrevia- 'disulfide' 27(T), 258, 260, 287, 417 tion 476(T) disulfides, of peptides 492 'E ' '(diethanolaminato)', ligand name for abbre- 'disulfinyl-', multivalent substituent 34(T) assignment of configuration 561 viation 476(T) '-disulfinyl-' and analogs, prefixes 416 CA stereodescriptors until 1999 574ff. '(N,N-diethyldithiocarbamato)', ligand name '(disulfite)' 239 citation in names 572 for abbreviation 478(T) 'disulfone' and analogs 27(T), 416 hydrazones 330, 341 '(diethylenetriamine)', ligand name for 'disulfonyl-', multivalent substituent 34(T) hydrocarbon chains 55 abbreviation 476(T), 588 '-disulfonyl-' and analogs, prefixes 416 imines 367 '(diethylenetriaminepentaacetato)', ligand 'disulfoxide' and analogs 27(T), 416 oximes 329, 340 name for abbreviation 476(T) 'disulfuric acid' 239 'E '/ 'Z ', stereodescriptor 572 '[diethylenetriaminepentakis(~ 'disulfurous acid' 239 '(ea)', ligand-name abbreviation 476(T) phosphonato)]', ligand name 'ditellane' 355 'eburnamenine' 488 for abbreviation 476(T) 'ditelluride' 27(T), 258, 260, 287, 417 '-ecane', Hantzsch–Widman names 78(T) 'diethyl ether' 35, 412 diterpenes 522 '-ecin(e)', Hantzsch–Widman names 78(T) '(diethyl ether)', ligand name 453 'dithio-', multivalent substituent 34(T) 'EDC' 363 digraph, hierarchical 561, 566, 584 '(dithio)' and analogs, ligand names 443(T) '(edda)', ligand-name abbreviation 476(T) 'dihydrazide' 316 '-dithio' and analogs, radical names 164 'EDTA' 32 'dihydroercalciol' 527 '-dithio-' and analogs, infixes '(edta)', ligand-name abbreviation 447, 476(T) '(dihydrogen)', ligand name 452(T) in carboxylic acid names 214 '(edtmpa)', ligand-name abbreviation 478(T) '(dihydroxyarsino)-' 22(T) in sulfonic acid names and analogs 224 '(egta)', ligand-name abbreviation 478(T) '(dihydroxyphosphino)-' 22(T) '-dithio-' and analogs, prefixes 417 'eicosa-' 540(T) '-diide', polyanion 194 '(dithiocarboxy)-' 20(T), 215 'elaidic acid'/ 'elaidoyl-' 204 '-diium' dithiohemiacetals 349 element names 543(T) polycation 184 '-(dithioic) acid' 20(T), 214 CA and IUPAC variants 433 skeletal bonding 178 '(dithionate)' 239 metallocene 459 diketoses 496 'dithionic acid' 239 organometallic compounds 458 'dilactide' 268 '(dithionite)' 239 element symbols, italic 'dilia-' 540(T) 'dithionous acid' 239 bond descriptor in coordination names 463 'dimer of phenylanisylmethylphosphine', '-diuide', polyanion 194 in amide names 299 ligand name for abbreviation diuloses 496 in amine names 360 476(T) '-diyl-' in ester names 270, 273 '(dimethylacetamide)', ligand name for bridged fused-polycycle substituents 128, in ligand names 438 abbreviation 476(T) 149, 150 nonstandard valences 597 '4-(dimethylamino)pyridine' 361 carbomonocycle substituents 68, 148 elision 9 '(dimethylglyoximato)', ligand name for cation substituents 182 definition 4 abbreviation 451, 476(T) fused-polycycle substituents 87, 112, 115, '-ep(i)-' in bridge name 128 '(dimethyl sulfide)', ligand name 453 149, 150 general naming 15 '(dimethyl sulfoxide)', ligand name for abbre- heterochain substituents 62ff., 147 in heterochain names 62ff. viation 476(T) heteromonocycle substituents 75, 77, 82, in IUPAC names 19(T) '(dinitrogen)', ligand name 438, 452(T) 84, 150 in names of '-dioic acid' 203 hydrocarbon-chain substituents 56, 146 attached components '(diop)', ligand-name abbreviation 476(T) ring-assembly substituents 142, 152 CA 101 '(diox)', ligand-name abbreviation 476(T) spiropolycycle substituents 134, 138, 149, IUPAC 95 'dioxidane' 355, 410 150 bridges 125, 126(T) '(dioxidoazo)-' 339 von Baeyer bridged-polycycle substituents carboxylic acids 19(T), 214, 216, 218 multivalent substituent 34(T) 120, 149, 150 C-oxoacids 230 N-heterochains 374 '-diylium' (– 2 H–) 175, 184 fused polycycles with replacement 'dioxy-', multivalent substituent 34(T) '(dma)', ligand-name abbreviation 476(T) names 115 '-dioxy', radical name 164 'DMAP' 361 heteromonocycles 76, 81, 83 '-dioxy-', peroxides 410 '(dme)', ligand-name abbreviation 476(T) P- and As-oxoacids 22(T), 245 '-dioxy-' and analogs, esters 274ff. '(dmf)', ligand-name abbreviation 476(T) peroxy acids with suffix 19(T) '(dioxygen)', ligand name 438, 452(T) '(dmg)', ligand-name abbreviation 451, 476(T) S-, Se-, and N-oxoacids 238 '(dipamp)', ligand-name abbreviation 476(T) '(dmpe)', ligand-name abbreviation 476(T) spiropolycycles 133 'diphenylamine' 361 '(dmpm)', ligand-name abbreviation 476(T) sulfonic acids and analogs 19(T), 224, '(diphosphate)' 249 '(dmso)', ligand-name abbreviation 476(T) 225, 226 '' 26(T) 'DNA' 514 von Baeyer bridged polycycles 118 'diphosphine-1,2-diyl-', multivalent substitu- 'do-' 540(T) multiplying affixes 540(T) ent 34(T) 'docosa-' 540(T) '(en)', ligand-name abbreviation 439, 478(T) 'diphosphoramide' 291 'dodeca-' 540(T) enantiomers 558, 559, 583 'diphosphoric acid' 249 donor-atom descriptor 438 enclosing marks 9 'diphosphorous tetraamide' 291, 307 'dopa' 214 brackets, for isotopically labeled com- 'diphosphorous tetrachloride' 291 double-bond isomers, indicated H atom 547 pounds 600 '(dipivaloylmethanato)', ligand name for double bonds definition 4 abbreviation 476(T) cumulative, see cumulative double bonds general naming 15 directions for use 1 noncumulative, see maximum number of in formulas of coordination compounds disaccharides 505 noncumulative double bonds 472(T) 'diselane' 355 '(dpm)', ligand-name abbreviation 476(T) in ligand names 'diselenide' 27(T), 258, 260, 287, 417 '(dppe)', ligand-name abbreviation 476(T) of anionic ligands without κ or η '' 27(T) '(dppf)', ligand-name abbreviation 476(T) descriptors 442 'disilanehexol' 254 '(dppm)', ligand-name abbreviation 476(T) of 'ato' and 'ito' ligands 444 'disilathiane' 27(T) '(dppp)', ligand-name abbreviation 476(T) of bridge ligands 454 'disilazane' 362 'dT', nucleoside abbreviation 511 of cationic ligands 453 'disiloxane' 27(T) '(dtmpa)', ligand-name abbreviation 476(T) of neutral ligands 451 'dispiro-' 133, 135, 541 '(dtpa)', ligand-name abbreviation 476(T) with η descriptors 440 'distibene' 26(T) dummy atoms 559, 562, 584 with κ descriptors 438

617 Index

enclosing marks (cont.) cyclic 267 prefix 56 in peptide names 492 exception of the seniority 23(T), 267, 273 'ethyn(o)-', bridge name 126(T) parentheses, for isotopically substituted multiplicative names 270 '-etidine', Hantzsch–Widman names 78(T) compounds 600 of a common acid and a common alcohol '-etine' 77 end groups, carotenoids 524 269 'eudesmane' 522, 576 ending of a common acid and an exotic alcohol 'eugenol' 414 compound classes 19ff.(T) 270, 273 Ewens-Bassett number, see charge number definition 4 of amino acids 491 'exo' general naming 13 of an exotic acid and any alcohol 270 CA stereodescriptors until 1999 573ff. 'endo' of a polybasic common acid and a com- citation in names 572 CA stereodescriptors until 1999 573ff. mon and/or exotic alcohol 269 von Baeyer bridged polycycles 120, 573 citation in names 572 of boric acids 254 exotic acids 268 in bridge name 125 of boronic and borinic acids 255 exotic alcohols and chalcogen analogs 268 von Baeyer bridged polycycles 120, 573 of carbohydrate acids 498 extended tetrahedron, obsolete in the CIP 'endo-cyclopent(a)-', bridge name 126(T) of monosaccharides 503 system 561 'endo-oxirano-', bridge name 128 of nucleosides 510, 512 'endo-pyrrolo-', bridge name 128 of peptides 492 '-ene' of polymers 531 'fac-' 588 carbomonocycles 67 of silicic acids 253 factorization rule 559 heterochains 61ff. oligonucleotides 512 'farnesol' 522 heteromonocycles 82 replacement names 61 'farnesyl-' 58 hydrocarbon chains 55 salts 278 'farnoquinone' 528 monosaccharides 503 seniority 23(T) 'ferrocene' 460 polymers 531 Si compounds 267, 404, 406 'ferrocenyl', ligand name 438 spiropolycycles 134 'estrane' 516 final syllable, definition 4 steroids 517 'Et', ligand-name abbreviation 478(T) Fischer projection 494, 499, 557 subtractive nomenclature 37 eta descriptor, see η descriptor 'flavone' 342 von Baeyer bridged polycycles 118 '-etane', Hantzsch–Widman names 78(T) flavylium' 179 '-enyl-' '(Et2dtc)', ligand-name abbreviation 478(T) 'fluora-' 543(T) carbomonocycle substituents 67, 148 '-ete', Hantzsch–Widman names 78(T) 'fluoranthene' 89(T) hydrocarbon-chain substituents 56, 146 '-etene' 77 '9H-fluorene' 89(T) '-enylidene-' 'etha-' 540(T) 'fluoride' 285ff. carbomonocycle substituents 68, 148 'ethane-1,2-diyl-' fluorides, see acid halides hydrocarbon-chain substituents 56, 146 multivalent substituent 34(T) 'fluoro', ligand name 442(T) '-enylidyne-' prefix 56 'fluoro-' 18(T), 288, 292, 429 hydrocarbon-chain substituents 56, 146 'ethan(o)-', bridge name 126(T), 541 'fluoronio-' 182 enzymes, lit. 536 '(ethanolaminato)', ligand name for abbre- 'fluoronium' 170 '-epane', Hantzsch–Widman names 78(T) viation 476(T) '(fod)', ligand-name abbreviation 478(T) IUPAC 78(T) 'ethanolamine' 29, 362 folic acids 493 'epi-' 125 'ethanylylidene-', bridge name 126(T) '' 327 'epidioxy-' 'ethen(o)-', bridge name 126(T) '' 231, 299, 300 bridge name 126(T) '6,14-ethenomorphinan' 488 'formamidine' 231 steroids 518 ethers 27(T) 'formate' 190, 234, 271 'epidithio-', bridge name 126(T) acyclic 411 'formazan' 314, 325 'epi-inositol' 509 functional-class nomenclature 38 formazans 24(T), 325, 330, 333, 341 '-epin(e)', Hantzsch–Widman names 78(T) of peptides 492 '' 21(T), 229 'epithio-' 'ethionine' 491 formic acids 229 bridge name 126(T) 'ethoxide' 191 formal hydrazides 314 steroids 518 'ethoxy', radical name 164 seniority 21(T) '(epithioethan(o))-', bridge name 126(T) 'ethoxy-' 18(T) 'formimidoyl-' 157, 233 '(epithiomethanothio)-', bridge name 126(T) alcohols 351 'formohydrazonoyl-' 157, 233 'epoxy-' esters 277 formulas alkaloids 489 ethers 412 of coordination compounds 472(T) bridge name 126(T), 409 '-ethoxy-', esters 275 of stereoparents, location of drawings 487 carotenoids 524 'ethyl', ligand name 442(T) primed locants in 52 nondetachable name part 541 'ethyl alcohol' 348 'formyl', halide suffix 285 prefix in stereoparent names 409 'ethylcalciol' 528 'formyl-' steroids 518 'ethyldipropylamine' 361 aldehydes 24(T), 327 '(epoxy[1,2]benzen(o))-', bridge name 126(T) '' 57 amides 303 '(epoxyethanylylidene)-', bridge name 126(T) 'ethylene-' 56, 58 C-oxoacids 233 '(epoxyimino)-', bridge name 126(T) 'ethylenediamine' 361 esters 275 '(epoxymethanoxy)-', bridge name 126(T) '(ethylenediamine)', ligand name for abbre- isolated group 156, 157 '(epoxymethenonitrilo)-', bridge name 126(T) viation 439 prefix 153 '(epoxynitrilo)-', bridge name 126(T) '(ethylenediaminediacetato)', ligand name '-formyl-' 601, 603, 605 '(epoxythio)-', bridge name 126(T) for abbreviation 476(T) 'formyl halide' 231 'ercalciol' 527 'ethylenediaminetetraacetamide' 301 '-formylium' 176 'ergocalciferol' 527 '(ethylenediaminetetraacetato)', ligand name free valence 'ergoline' 488 for abbreviation 447, 476(T) assignment of 'added' indicated H atom 'ergostane' 516 'ethylenediaminetetraacetic acid' 32, 210 553f. 'ergotaman' 488 '[ethylenediaminetetrakis(methylenephos~ assignment of indicated or 'added' indi- 'erythrinan' 488 phonato)]', ligand name for cated H atom 552 'erythro-' 496 abbreviation 478(T) locants 49, 50 'erythrose' 495 '' 347 no indicated H atom 553 'ester' 270 '[ethylene glycol-bis(2-aminoethyl)-N,N,Nʹ,Nʹ- 'friedo-' 524 esters 267 tetraacetic acid]', ligand name for 'fructan' 507 acyclic abbreviation 478(T) 'fructose' 495 classification 268 'ethylidene-' '(fta)', ligand-name abbreviation 478(T) naming 270ff. multivalent substituent 34(T) 'fucose' 503

618 Index fullerenes, lit. 536 orientation prior to numbering 107 'glyceramide' 301 '' 230, 321 replacement names 114 'glyceric acid'/ 'glyceroyl-' 209 '' 141 saturated or partially saturated 'glyceride' 271, 273 'fulvene' 69 with fusion names 112 'glycero-' 495 'fumaraldehyde' 331 with replacement names 115 'glycerol' 271, 347 'fumaramide' 301 with semitrivial or trivial names 86 '(glycinato)', ligand name for abbreviation 'fumaric acid'/ 'fumaroyl-' 204 semitrivial or trivial names 86ff. 478(T) functional-class names Si-containing 95, 114 '(glycinato-κO)', ligand name 446 acyclic monosulfones, monosulfoxides, with bridges 123 ''/ 'glycyl-' 210, 490 monosulfides, and analogs 420f. fused-polycycle substituents, prefixes 87, 'glyco-' 508 alcohols 347 112, 115, 149, 150 '' 328 azides 379 fused polycycles with bridges, see bridged 'glycolamide' 301 cyanates 321(T) fused polycycles 'glycolic acid'/ 'glycoloyl-' 209 cyanides 321(T) fusion names 'glycolipid' 271 definition 4 choice (seniority) glycolipids, see IUPAC ethers 412 of parent component 89(T), 91(T), 98 glycopeptides, see IUPAC halogen compounds 429 of the senior attached component 101 glycoproteins, see IUPAC hydroperoxides 355 definition 5 glycosides 504f. isocyanates 379 fused polycycles 95 glycosylamines 504 isocyanides 321(T), 379 general procedure 95ff. 'glycosylglycose' 505 isofulminates 321(T) porphyrins 529 'glycosyl glycoside' 505 isothiocyanates and analogs 321(T), 379 steroids 518 glycosyl halides 504 ketones 335, 337 fusion side glycosyl substituents 504 nitriles 322 parent component 103 'glycuronan' 507 peroxides 410 primary attached component 103 'glyoxal' 328 polyoxides 410 fusion site 'glyoxylamide' 301 polysulfides and analogs 417 fused polycycles 103ff. 'glyoxylic acid'/ 'glyoxyloyl-' 209 polysulfones and analogs 416 higher-order attached component 106 'gonane' 516 polysulfoxides and analogs 416 graft polymers 534 thiocyanates and analogs 321(T) graphical representations of structures 557 functional-class nomenclature (see also 'G ', nucleoside abbreviation 511 Greek letters, locants 49 functional-class names) 38 'galacto-' 495 'Green Book' 599 general naming 14 'galactose' 495 group, see characteristic group, isolated group , see characteristic group 'gallic acid'/ 'galloyl-' 209 '(gua)', ligand-name abbreviation 478(T) functional modifier, see modification 'gammacerane' 523 'guaiacol' 348, 414 'functional-parent names' Ge compounds 403, 458 'guaiane' 522 amines 359, 360 seniority 27(T) 'guanidine' 231, 304 imines 368 stereodescriptors 582, 585 '-guanidinium' (+ E+) 174 functional-parent names Ge-heterochains 405 'guanidino-' 158, 231, 305 carbonic and formic acids 229 Ge-heterocycles 403 'guanine' 309, 510 compound classes 19ff.(T) general names, definition 5 '(guanine)', ligand name for abbreviation definition 4 'geraniol' 351, 521 478(T) for identical structure units, multiplicative 'geranyl-' 58 'guanosine' 511 nomenclature 32 'geranylfarnesol' 523 '(guanosine)', ligand name for abbreviation general naming 13 'germa-' 543(T) 478(T) not conjunctive nomenclature 30 '' 27(T), 63, 405 'guanylic acid' 511 P- and As-oxoacids 243 germanium compounds, see Ge compounds 'guanylyl-' 512 S-, Se-, Te-, and N-oxoacids 237 'german(o)-', bridge name 126(T) 'gulo-' 495 seniority 41 germaselenanes 65 'gulose' 495 Si- and B-oxoacids 253 'germin' 78(T) '(guo)', ligand-name abbreviation 478(T) substitutive nomenclature 29 'germyl-' 64, 405 functional parents (see also functional-par- 'germylene-' 405 ent names), definition 6 'germylidyne-' 405 'H ', indicated H atom 547ff. fundamental fused carbopolycycles, semi- 'gibbane' 522 ' 2H' 599(T) trivial or trivial names 89(T) gibbelerins 522 ' 3H' 599(T) fundamental heterocycles, semitrivial or '(gln)', ligand-name abbreviation 478(T) halides, see acid halides trivial names 91(T) '(glu)', ligand-name abbreviation 478(T) '(halocarbonyl)-' 24(T) fundamentals 3 'gluco-' 495 halogen atoms, cationic, in heteromono- 'fural' 331 'glucose' 495 cycles 76 'furaldehyde' 331 'glutamate' 221 halogen compounds 27(T), 429 'furamide' 301 '(glutamato)', ligand name for abbreviation cyclic 430 'furan' 73, 92(T) 478(T) ionic 430 'furano-', bridge name 126(T), 128 'glutamic acid'/ 'glutamoyl-'/ 'glutamyl-' 210, Hantzsch–Widman names 76 'furazan' 75 490 definition 5 'furfural' 328, 331 'glutaminate' 221 final syllables 78(T) 'furfuryl-' 76 '(glutaminato)', ligand name for abbreviation Si-containing fused polycycles 95 'furo-' 92(T), 102 478(T) hapto ligands 440 'furoic acid'/ 'furoyl-' 205 'glutamine' 299 stereodescriptors 591 'furoin' 338 'glutamine'/ 'glutaminyl-' 210, 490 hapto symbol, see η descriptor furostanes 516 'glutamyl-' 492 'hasubanan' 488 'furyl-' 76, 88 'glutaraldehydic acid' 328 Haworth projection 494, 499, 557 '2H-furylium' 179 'glutaramide' 301 '21H-biline' 530 fused heterobicycle, see benzoheteromono- 'glutaric acid'/ 'glutaryl-' 204 '(hdtmpa)', ligand-name abbreviation 478(T) cycle '(gly)', ligand-name abbreviation 478(T) heading parent fused polycycles 85 'glycan' 507 anhydrides 257 five- and seven-membered ring compo- glycans 507 coordination compounds nents 2, 85, 123 'glyceral' 331 anionic 461 fusion names 95 'glyceraldehyde' 331, 495, 571 cationic 456

619 Index

heading parent heteromonocycle substituents, prefixes 75, '(S-hydrazinosulfonimidoyl)-' 20(T), 225 coordination compounds (cont.) 77, 82, 84, 150 '(hydrazinosulfonyl)-' 20(T), 225 neutral 458 'hetero'-polyboranes 397 'hydrazin-1-yl-2-ylidene-' polynuclear 464 hetero unit, replacement nomenclature 61 hydrazides 315 definition 5 'hetisan' 488 hydrazones 330, 341 esters 267 'hexa-' 540(T) multivalent substituent 34(T) hydrazides 313 'hexacene' 90(T) N-heterochains 64, 147, 373 hydrazones 326 '(hexafluoroacetylacetonato)', ligand name 'hydrazo-' in 'Chemical Substance Index' of CA 41 for abbreviation 478(T) hydrazides 315 isotopically modified compounds 601 'hexahelicene' 90(T) hydrazones 330, 341 metallocenes 459 '[hexamethylenediaminetetrakis(methylene~ multivalent substituent 34(T) order of prefixes 155 phosphonato)]', ligand name for N-heterochains 64, 147, 373 organometallic compounds 458 abbreviation 478(T) steroids 518 oximes 326 '(hexamethylenetetraamine)', ligand name '(hydrazodicarbonyl)-', multivalent substitu- peptides 492 for abbreviation 478(T) ent 34(T) seniority 45 'hexaphene' 90(T) '' 237 'hecta-' 540(T) 'hexose' 496 '-hydrazonamide' 298(T) '(hedp)', ligand-name abbreviation 478(T) hexoses 494 'hydrazonato', ligand name 444 'helicene' 90(T) hex-2-uloses 495 '-hydrazone' 330, 341 helicity 560 '(hfa)', ligand-name abbreviation 478(T) hydrazones octahedron 583 hierarchical digraph 561, 566, 584 of acid halides 325 helicity rule 560 higher-order attached component 101, 106 of acids 23(T) helix unit 560 'hippuric acid' 491 of aldehydes 24(T), 325 hemiacetals 24(T), 326, 347, 349 'hippuric acid'/ 'hippuroyl-' 212 seniority 24(T) hemiacetals, monosaccharides 498, 499 '(his)', ligand-name abbreviation 478(T) of amides 325 hemiaminals 326 '(histidinato)', ligand name for abbreviation of carboxylic acids 325 'hen-' 540(T) 478(T) of ketones 24(T), 333 'heneicosa-' 540(T) 'histidine'/ 'hystidyl-' 211, 490 seniority 24(T) 'henicosa-' 540(T) 'HMPA' 307 of monosaccharides 503 'hepta-' 540(T) '(hmpa)', ligand-name abbreviation 478(T) of polymers 531 'heptacene' 90(T) 'HMPT' 307 '-hydrazonic acid' 20(T), 216 'heptalene' 89(T) '(hmta)', ligand-name abbreviation 478(T) 'hydrazono-' 'heptaphene' 90(T) 'HOBt' 350 acid halides 288 'heptose' 496 'homo-' amides 303, 305 '(heteroarenido)', ligand names 448 alkaloids 489 carboxylic acids 217 heteroatom bridgeheads, indicated H atom nondetachable name part 541 C-oxoacids 233 549 steroids 517 esters 275, 276, 278 heteroatom prefixes, see heteroatom syllables triterpenes 524 hydrazides 315ff. heteroatoms 'homoadamantane' 425 hydrazones 330, 341 general naming 13 'homocysteine'/ 'homocysteinyl-' 211, 490 imines 368 standard valence 61, 73, 85, 117, 123, 133, homoglycans 507 N-heterochains 64, 147, 373 141, 543(T) homopolymers 467, 534 prefix 156f. heteroatom syllables 543(T) 'homoserine'/ 'homoseryl-' 211, 490 radicals 163 definition 5 'hopane' 524 '-hydrazon(o)-', infix in names in fused polycycles with replacement 'hydantoic acid'/ 'hydantoyl-' 214 of carboxylic acids 216 names 114 'hydantoin' 309 of C-oxoacids 230 in heterochain names 61ff. 'hydantoyl-' 305 of sulfonic acids and analogs 225 in heteromonocycle names 76, 81, 83f. hydrates 23(T) '(hydrazonomethyl)-' 233 in metallocene names 459 of aldehydes 349 '-hydrazonoyl', acid halide suffix 286(T) in names of anionic coordination com- of ketones 351 'hydrazyl' 161 pounds 461 of monosaccharides 503 'hydrido', ligand name 442 in spiropolycycle names 133 'hydrazi-', N-heterochains 64, 147, 373 'hydro', ligand name 438, 442, 442(T) in von Baeyer bridged-polycycle names 'hydrazidato', ligand name 444 'hydro-' 36 118 'hydrazide' 188, 317 alkaloids 489 multiplying affixes 539 '-hydrazide' 314 alphabetical order 53 heterochains 61 hydrazides 313 carotenoids 524 formal hydrazides 314 acyclic 314 general naming 17 heterogeneous, with regular patterns 65 amino acids 491 locants 50 homogeneous 62 boric acids 254 nonstandard valences 596 with irregularly placed heteroatoms 61 boronic and borinic acids 255 standard valences 597 with regularly placed heteroatoms 62 carbohydrate acids 498 'hydroantimonate(2–)' 188 heterochain substituents, prefixes 62ff., 147 cyclic 313 hydrocarbon-chain component, in conjunc- '-heterocycloalkin(e)', fusion names 100 exception of the seniority 23(T) tive nomenclature 30 'heterocycloalkino-', fusion names 102 replacement names 61 hydrocarbon chains 55 heteroglycans 508 seniority 24(T) branched 57, 426 heteromonocycles 73 'hydrazidine' 314 Ph-substituted 55 'cyclo-' names 83f. '-hydrazid(o)-', infix in P- and As-oxoacid unbranched 55, 426 Hantzsch–Widman names 76ff. names 245 hydrocarbon-chain substituents, prefixes replacement names 81f. '' 26(T), 63 55ff., 146 saturated or partially saturated '(hydrazine)', ligand name 452(T) with Hantzsch–Widman names 77 hydrazinecarboxylic acid, formal anhydride numerical syllables 540(T) with trivial names 75 258 'hydrochloric acid' and analogs 237 Si-containing 82ff. '[hydrazinium(1+)]', ligand name 453(T) 'hydrocyanic acid' 231, 322 trivial names 73 'hydrazino-' 'hydrogen' with cationic halogen atoms 76 hydrazides 315ff. for ligands with noncoordinating acid with metal atoms 76 N-heterochains 64, 147, 373 functions 444 with more than ten ring members 81 '-hydrazino-', S-, Se-, Te-, and N-oxoacids 240 in coordination names 456, 462 with up to ten ring members 76ff. '(hydrazinocarbonyl)-' 20(T), 24(T), 216, 315 in ester and salt names 279

620 Index

in ester names 270, 273 '-ic acidium' (+ E+) 173 ent 34(T) in salt names 220, 227, 234, 249 'icosa-' 540(T) '(iminoethanimino)-', bridge name 126(T) 'hydrogen names', inorganic acids 237, 244 '(ida)', ligand-name abbreviation 446, '(iminomethyl)-' 233 '()', ligand name 452(T) 478(T), 588 '-iminyl' 164 '' 237 '-ide' '-iminylium' 177 '' 237 anion 19(T), 189 '-inane', Hantzsch–Widman names 78(T) '(hydrogen sulfide)', ligand name 452(T) lactides 268 IUPAC 78(T) 'hydron' 169, 187 identical ring components 141 '-inato', ligand name 444 'hydroperoxide' 25(T), 355 determination of molecular-skeleton 'as-indacene' 89(T) hydroperoxides 38, 355 parents 41 's-indacene' 89(T) seniority 25(T) multiplying affixes 539 'indane' 87 'hydroperoxo', radical name 163 ring assemblies 32 '1H-indazole' 93(T) 'hydroperoxy', ligand name 442(T) identical structural units 32 '1H-indene' 89(T) 'hydroperoxy-' 25(T), 153, 219, 355, 356 'ido-' 495 'Index Guide' 1, 5, 487 '(hydroperoxycarbonyl)-' 19(T), 219 '-ido', ligand names 442, 450 index names '(hydroperoxysulfinyl)-' 19(T), 226 '-ido-', anion (prefix) 194 amide and hydrazide tautomers of car- '(hydroperoxysulfonyl)-' 19(T), 226 '-idone' 295, 334 boximidic and carbohydrazonic '(hydroperoxythio)-' 19(T), 226 'idose' 495 acids 216 hydropolychalcogenides 355 '-iduide', polyanion 194 amide and hydrazide tautomers of sul- 'hydroquinone' 347 '-idyl-', anion (prefix) 194 fonimidic and sulfonohydrazonic 'hydrotetraoxide' 355 '(ile)', ligand-name abbreviation 478(T) acids and analogs 224, 225 '(hydrotetraoxy)-' 355 '(im)', ligand-name abbreviation 478(T) CA 1 'hydrotrioxide' 355 '-imidamide' 298(T) choice (seniority) 13 '(hydrotrioxy)-' 355 'imidazo-' 92(T), 102 definition 5 '[hydrotris(3,5-dimethylpyrazolyl)borato]', '1H-imidazole' 74, 92(T) for ligand names, senior 438 ligand name for abbreviation 'imidazolidine' 74 noninversion of the name components 2 484(T) 'imidazoline' 74 order in 'Chemical Substance Index' of CA '[hydrotris(pyrazolyl)borato]', ligand name '-imide' 296, 301 45 for abbreviation 484(T) anion 190 position of locants 2, 49 'hydrotrisulfide' and analogs 355 imides 23(T), 295, 296, 301 seniority 48 '(hydrotrithio)-' and analogs 355 seniority 24(T) with modification 159 'hydroxamic acid' 376 '-imidic acid' 20(T), 216 'Index of Ring Systems' 'hydroxy', ligand name 438, 442(T) '-imidium' (+ E+) 173 bridged fused polycycles 123 'hydroxy-' 25(T), 153, 347, 350 'imido', ligand name 438, 443(T) fused polycycles 85 N-hydroxyamine 363 'imido-', affix in names heteromonocycles 73 '(hydroxyamino)-' 363, 375 of polynuclear C-oxoacids 232 ring assemblies 141 '[(hydroxyamino)iminomethyl]-' 298(T) of polynuclear P- and As-oxoacids 249 spiropolycycles 133 '(hydroxyarsinidene)-' 22(T) of polynuclear S- and Se-oxoacids 239 von Baeyer bridged polycycles 117 '(hydroxyarsinylidene)-' 22(T) of S-, Se-, and N-oxoacids 238 indicated H atom 547 '(hydroxyborylene)-' 23(T), 400 '-imid(o)-', infix in names bridged fused polycycles 123, 128 hydroxycarboxylic acids 208f. of carboxylic acids 216 cations 170, 179 '(1-hydroxyethane-1,1-diyl)diphosphonato]', of C-oxoacids 230 definition 5 ligand name for abbreviation of P- and As-oxoacids 245 fused polycycles 478(T) of sulfonic acids and analogs 225 with fusion names 97, 112 '(hydroxyimino)-' 329, 340, 363 '-imido-' 296 with replacement names 115 'hydroxyl', radical name 163 'imidodicarbonic acid' 21(T), 232 with semitrivial or trivial names 86, hydroxylamines '' 163 89(T), 91(T) alcohols 350 '-imidogen' 164 heteromonocycles 75, 77 amines 363 '-imidoperoxoic acid' 219 imines 367 formal amides 299, 304, 306, 307 'imidosulfurous acid' 21(T) ketones 333 N-heterochains 375 '-imidoyl', acid halide suffix 286(T) nondetachable name part 541 pseudoesters 267 '-imidoyl-', acyl prefix 217 nonstandard valences 594 seniority 26(T) '-iminato', ligand name 444 numbering 50 substituted, formal 375 '-imine' 25(T), 367 ring assemblies 141 'hydroxylamine-O-sulfonic acid' 238, 375 bridge name 124 spiropolycycles 136 oximes 325 imines 367 'indicated hydrogen' 547 'hydroxyoxomethyl', radical name 163 N-alkyl- and N-aryl-substituted, formal '1H-indole' 93(T) '(hydroxyphosphinidene)-' 22(T) 359, 368 'indoline' 87 '(hydroxyphosphinylidene)-' 22(T) seniority 25(T) 'indolizine' 93(T) 'N-hydroxy…carboximidamide' 298(T) 'iminio-' 182 '-in(e)' 'N-hydroxy…imidamide' 298(T) '-iminium' (+ E+) 173 fused heteropolycycles with semitrivial 'hypoboric acid' 254 'iminium ylide' 197 names 92 'hypochlorite' and analogs 237 'imino-' 25(T) Hantzsch–Widman names 78(T) 'hypochlorous acid' 287, 289, 291 acid halides 288 infixes 'hypochlorous acid' and analogs 237 amides 305 carboxylic acids 19(T), 214, 216, 218 'hyponitrate' 238 amines 360 C-oxoacids 229 'hyponitric acid' 238 bridge name 124, 126(T) definition 5 'hyponitrite' 238 carboxylic acids 217 in IUPAC names 19(T) '[hyponitrito(2–)]', ligand name 445(T) C-oxoacids 233 P- and As-oxoacids 22(T), 245 'hyponitrous acid' 238 esters 275, 276, 278 peroxy acids with suffix 19(T) 'hypophosphonic acid' 249 imines 367f. sulfonic acids and analogs 19(T), 224, 'hypophosphonous acid' 249 multivalent substituent 34(T) 225, 226 'hypophosphoric acid' 249 prefix 156f. '-inidene-', mononuclear substituents 145 'hypoxanthine' 309, 510 radicals 163 '-inidyne-', mononuclear substituents 145 '-imino-', amides 303ff. '-inine', Hantzsch–Widman names, IUPAC '(iminodiacetato)', ligand name for abbrevia- 78(T) ' I ', nucleoside abbreviation 511 tion 446, 478(T), 588 'inner salt', zwitterion 195, 196 'ibogamine' 488 '(iminodicarbonyl)-', multivalent substitu- '-ino-', mononuclear substituents 145

621 Index

inorganic acids 237, 243, 244 'isodiazene' 373 numbering 51 inorganic compounds, lit. 536 isofulminates, functional-class names 321(T) isotopically modified compounds, by CA 'inosine' 511 'isofulminato-' 321(T) (D) and tritium (T) isotopes 'inosinic acid' 511 'isofulminic acid' 230 602ff. 'inosinylyl-' 512 'isoglutamine' 300 not localized isotope modification 608 inositols 509 'isoguanosine' 511 organometallic and coordination com- 'inosose' 509 'isohexyl-' 58 pounds 607 interior atoms, numbering of fused poly- '2H-isoindole' 93(T) other isotopes than D and T 605 cycles 'isoindoline' 87 isotopically substituted compounds, by CA 110 isolated group, definition 5 IUPAC 600 IUPAC 95 isolated ligand, in stereoisomers 559 'isourea' 230, 304 'interior chain', numbering of interior atoms '(isoleucinato)', ligand name for abbreviation 'isoureido-' 305 of fused polycycles 110 478(T) 'isovaleric acid'/ 'isovaleryl-' 204 International Union of Pure and Applied 'isoleucine'/ 'isoleucyl-' 211, 490 'isovaline'/ 'isovalyl-' 211, 490 Chemistry, see IUPAC isomers 'isoviolanthrene' 87 Internet 537 carboperoxoic acids 219 'isoxazole' 74, 79, 92(T) '-io-', cation (prefix) 19(T), 182 C-oxoacids with peroxy infixes 230 'isoxazolidine' 74, 79 'ioda-' 543(T) stereoisomers 557 'isoxazoline' 74 'iodane' 429 sulfonoperoxoic acids and analogs 226 italic Roman letters, locants 49 'iodide' 285ff. 'isonicotinamide' 301 '-ite' iodides, see acid halides '(isonicotinamide)', ligand name for abbre- acid anion (salt) 190, 249 iodine-containing heterocycles, nonstandard viation 478(T) esters 270, 273, 279 valences 596 'isonicotinic acid'/ 'isonicotinoyl-' 205 '-ito', ligand names 442, 444 'iodo', ligand name 442(T) 'isonitrile' 321 '-itol' 497 'iodo-' 18(T), 288, 292, 429 '' 57 IUB, see IUPAC iodomonocycles, neutral 81 'isopentyl-' 57 IUBMB, see IUPAC 490 'iodonio-' 182 '2H-isophosphindole' 91(T) '-ium' 'iodonium' 170 'isophosphinoline' 91(T) cation (+ E+) 19(T), 170 'iodosyl-' 18(T), 429 'isophthalamide' 301 polycation 184 'iodyl-' 18(T), 429 'isophthalic acid'/ 'isophthaloyl-' 205 skeletal bonding 178 ' ion(1–)' 189ff. 'isoprene' 57 '-iumide', zwitterion 195 'ipso' 69 'isoprene' units 524 '-iumuide', zwitterion 195 '-irane', Hantzsch–Widman names 78(T) 'isopropenyl-' 56, 57, 58 '-iumyl', radical cation 200 'irehamine' 519 'isopropoxy-', ethers 412 '-iumyl-', cation (prefix) 19(T), 182 '-irene', Hantzsch–Widman names 78(T) 'isopropyl-' 56 IUPAC 1 '-iridine', Hantzsch–Widman names 78(T) 'isopropyl alcohol' 348 'Blue Book' 1, 3 '-irine', Hantzsch–Widman names 78(T) 'isopropylamine' 360 conformation '(isn)', ligand-name abbreviation 478(T) 'isopropylidene-' 57, 58, 146 of polynucleotide chains (1983) 510 'iso-', nondetachable name part 541 'isoquino-' 93(T), 102 of polypeptides (1974) 490 '2H-isoarsindole' 91(T) 'isoquinoline' 93(T) of polysaccharides (1983) 494 'isoarsinoline' 91(T) 'isoquinolone' 296, 334 fusion names (1998) 85 'isoasparagine' 300 'isoquinolyl-' 88 glossary of basic terms for polymers 'isobenzofuran' 92(T), 97 'isoselenazole' 74, 79, 92(T) (1996) 531 'isobenzofuro-' 92(T) 'isoselenazolidine' 74, 79 'Green Book' 599 'isobenzofuro-' and chalcogen analogs 102 'isoselenocyanato-' 18(T) Internet 537 'isobutane' 57 'isosemicarbazide' 325 names 'isobutoxy-', ethers 412 isosemicarbazides 216 for amino acids and peptides (1984) 490 'isobutyl-' 57 'isosemicarbazone' 326 for bridged fused polycycles (1998) 123 'isobutyl alcohol' 348 isosemicarbazones 24(T), 216 for carbohydrates (1996) 494, 526 'isobutyramide' 301 'isotellurazole' 74, 79 for carotenoids (1975) 520 'isobutyric acid'/ 'isobutyryl-' 204 'isotellurazolidine' 74, 79 for copolymers, source-based (1985) 'isocarbonohydrazide' 326 'isotellurocyanato-' 18(T) 531 isocarbonohydrazides 216 'isothiazole' 74, 79, 92(T) for corrinoids (1976) 526 'isochromane' 87 'isothiazolidine' 74, 79 for cyclitols (1974) 509 'isochromene' 92(T) 'isothiochromane' and chalcogen analogs 87 for folic acids (1987) 490 'isochromenylium' 179 'isothiochromene' and chalcogen analogs for fused polycycles (1998) 85 'isocrotonic acid'/ 'isocrotonoyl-' 204 92(T) for glycolipids (1997) 494, 509 'isocyanate' 285ff. 'isothiocyanate' and analogs 285ff. for glycoproteins, glycopeptides, and isocyanates isothiocyanates and analogs peptidoglycans (1988) 490, 494 functional-class names 38, 321(T) functional-class names 321(T) for incompletely specified bases in see acid halides see acid halides nucleic acid sequences (1985) 510 '-isocyanatid(o)-', infixes in names 'isothiocyanato-' 18(T) for inorganic radicals and radical ions of C-oxoacids 229 'isothiocyanato-' and analogs 288, 292, (2005) 161 of P- and As-oxoacids 245 321(T), 378 for irregular single-strand organic 'isocyanato-' 18(T), 288, 292, 321(T), 378 affix in S-, Se-, and N-oxoacid names 238 polymers, structure-based (1994) affix in S-, Se-, and N-oxoacid names 238 'isothiourea' and analogs 230 531 '' 230, 321 isotope composition, natural 599 for metal complexes of tetrapyrroles 'isocyanide' 285ff., 321 isotope descriptor (2000) 529 isocyanides by CA 601 for monoterpenes (1979) 520 functional-class names 38, 321(T) position in names for natural products (1999) 487, 516, see acid halides CA 601 520 '-isocyanid(o)-', infix in names IUPAC 600 for nonlinear macromolecules and of C-oxoacids 229 isotopically deficient compounds 600 macromolecular assemblies, of P- and As-oxoacids 245 isotopically labeled compounds, by IUPAC source-based (1997) 531 'isocyano-' 18(T), 288, 292, 321(T), 378 600 for polymers, generic source-based affix in S-, Se-, and N-oxoacid names 238 isotopically modified compounds 599 (2001) 531 'isocyanogen' 163 by CA 601 for prenols (1987) 520 'isocyanyl' 163 by IUPAC 600 for radicals, ions, and radical ions

622 Index

(1993) 161, 169, 187, 195, 199 'lanostane' 523 Arabic numerals 49 for regular organic ladder or spiro 'lanthionine' 212, 492 citation in names 52 polymers (1993) 531 'lauric acid'/ 'lauroyl-' 204 definition 6 for regular single-strand organic poly- compounds, see Pb compounds for stereodescriptors 572 mers (2002) 531 letter locants general naming 14 for regular single-strand or quasi in amide names 299 Greek letters 49 single-strand inorganic and coor- in amine names 360 indefinite 50 dination polymers (1985) 531 in ester names 270, 273 in peptide names 492 for retinoids (1983) 520, 526 in ligand names 438 in the isotope descriptor (IUPAC) 600 for spiropolycycles (1999) 133 numbering 49 italic, in the isotope descriptor (CA) 601 for steroids (1989) 516, 526 '(leu)', ligand-name abbreviation 478(T) italic Roman letters 49 for synthetic polypeptides (1973) 490 '(leucinato)', ligand name for abbreviation in alkaloid names 489 for tetrapyrroles (1987) 529 478(T) order in names 49 for tocopherols (1982) 526 'leucine'/ 'leucyl-' 211, 490 position in names 49 for vitamin D (1982) 526 'levulinic acid'/ 'levulinoyl-' 209 primed, in formulas 52 for vitamins B6 (1996) 526 'ligand', nonsenior central atom 465 seniority order 49 for von Baeyer bridged polycycles ligand abbreviations 434, 472(T) unsaturations 49 (1999) 117 ligand formulas, alphabetical order 472(T) lone pair of electrons, transformation NMR structures of proteins and nucleic ligand names 438ff., 472(T) convention in the CIP system acids (1998) 490, 510 anionic heterocyclic ligands 448 564, 584 numbering of myo-inositol (1989) 509 anionic ligands 442ff. 'lumisterol' 527 phane nomenclature (1998 and 2002) 117, of acids 445 'lupane' 523 123 of alcohols 447 '(lut)', ligand-name abbreviation 478(T) recommendations A–F and H (1979) 1 of aldehydes and ketones 450 '(lutidine)', ligand name for abbreviation recommendations R (1993) 1 of amides 449 478(T) 'Red Book' 7, 433 of amines 449 'lycopene' 524 stereodescriptors for polymers (1981) 531 of esters 448 '(lys)', ligand-name abbreviation 478(T) symbols for nucleic acids and polynucleo- of oximes and hydrazones 450 '(lysinato)', ligand name for abbreviation tides (1974) 510 '-ato' 444ff. 478(T) IUPAC name, definition 5 bridge ligands 453 'lysine'/ 'lysyl-' 211, 490 cationic ligands 453 'lyxo-' 494 definition 5 'lyxose' 494 junction site, ring assemblies 142 in index names 438 '-ito' 444ff. ligands with noncoordinating acid func- 'm', see 'meta' kappa descriptor, see κ descriptor tions 444 'M ' 'kaurane' 523 neutral ligands 451 assignment of configuration 560 ketals 326, 411 nonsenior central atom 465 citation in names 571 '' 335 order of identical ligand names with and main bridge of von Baeyer bridged poly- 'ketimine' 368 without κ descriptors 438 cycles 118 ketoaldoses 496 with η descriptors 440 main ring of von Baeyer bridged polycycles hydrate 351 with κ descriptors 438 118 ketone hydrazones 333, 341 with µ descriptors 454 choice (seniority) 119 ketone oximes 333, 340 without description of coordination site '(mal)', ligand-name abbreviation 478(T) ketones 333 438 '(malato)', ligand name for abbreviation acyclic 335 ligand number, in stereoisomers 561, 584 478(T) cyclic 333 ligands '(male)', ligand-name abbreviation 478(T) functional-class nomenclature 38 abbreviations 434, 472(T) 'maleamide' 301 not conjunctive nomenclature 30 anionic, ligand names 442ff. '(maleato)', ligand name for abbreviation seniority 25(T) cationic, ligand names 453 478(T) ketoses 496 definition 5 'maleic acid'/ 'maleoyl-' 204 '-ketyl' 201 in stereoisomers 559ff. 'maleic anhydride' 257 'kilia-' 540(T) isolated, in stereoisomers 559 '(maleonitriledithiolato)', ligand name for '-kis-' 539 mono- or polydentate 438 abbreviation 480(T) Klyne–Prelog convention 561 multiplying affixes 539 'malic acid'/ 'maloyl-' 209 neutral, ligand names 451 '(malo)', ligand-name abbreviation 480(T) polydentate, priority numbers 583 'malonaldehyde' 328 'l ', stereodescriptor, obsolete 572 rotationally equivalent, in stereoisomers 'malonaldehydic acid' 213 'l' 560 'malonamic acid' 212 amino acids 210, 490, 571 with noncoordinating acid functions 444 'malonamide' 301 carbohydrates 494, 571 ligand segment 5, 470, 582, 584 '(malonato)', ligand name for abbreviation cyclitols 509 lignans, lit. 536 480(T) peptides 571 'limonene' 521 'malonic acid'/ 'malonyl-' 204 'lactamide' 301 'linalool' 521 'mandelic acid'/ 'mandeloyl-' 209 lactams 23(T), 295 'linalyl-' 58 'mannan' 507 of peptides 492 linker, modified 'manno-' 495 'lactic acid'/ 'lactoyl-' 209 oligonucleotides 513 'mannose' 495 lactides 268 polynucleotides 514 mass numbers, sequence rules 566 lactims 23(T), 295 linking substituents, see multivalent sub- maximum number of noncumulative double 'lactoflavin' 526 stituents bonds lactones 23(T), 267, 268 'linoleic acid'/ 'linoleoyl-' 207 definition 6 of carbohydrate acids 498 'linolenic acid'/ 'linolenoyl-' 207 fused polycycles 85, 95, 97 of monosaccharides 503 , lit. 536 indicated H atom 547 of peptides 492 'lithio-' 436 nonstandard valences 594 of steroids 517 'lithium aluminum ' 437 'Me', ligand-name abbreviation 480(T) 'lactose' 505 locants 'menthadiene' 521 ladder polymers 532 alphanumerical, numbering of fused 'menthane' 520 lambda convention, see λ convention polycycles 108, 110 'menthene' 521

623 Index

'menthol' 351, 521 '' 360 not for coordination compounds 454, 463 '(2-Mepy)', ligand-name abbreviation 480(T) 'methylcalciol' 527 polycations 185 'mer-' 588 'methylene-' polyradicals 167 'mercapto' multivalent substituent 34(T) multiplicative nomenclature (see also multi- ligand name 438, 442(T) prefix 56, 146 plicative names) 32 radical name 163 '[methylenebis(oxy)]-', multivalent substitu- determination of molecular-skeleton 'mercapto-' 25(T), 153, 347, 350 ent 34(T) parents 47 '(mercaptoamino)-' 363, 375 'methylene chloride' 430 multiplicative prefixes, see multiplying '(mercaptoimino)-' 329, 340 'methylidene-' 56 affixes '(mercaptooxy)-' 25(T), 219, 355, 356 'methylidyne-' multiplying affixes539 , 540(T) 'mercuranthrene' 91(T) multivalent substituent 34(T) alphabetical order 53 'mesaconic acid'/'mesaconoyl-' 204 prefix 56 conjunctive nomenclature 30 'mesityl-' 69 'methyn(o)-', bridge name 125, 127(T) definition 6 'mesitylene' 69 Mills depiction 494, 499 for anions in coordination names 456 meso compounds 572, 573 '(mnt)', ligand-name abbreviation 480(T) for cations in coordination names 462 mesomeric ring structure, transformation modification for central-atom names 464 convention in the CIP system definition 6 for ligand names 562, 564, 584 for additive name parts (e.g., 'oxide') 159 of anionic ligands 442, 444 'mesoxalic acid'/ 'mesoxalyl-'/ 'mesoxalo-' 209 for ionic name parts 159 of anionic ligands without κ or η 'mesyl-' 226, 287, 421 in anhydride names 159, 258ff. descriptors 442 'mesylate' 226 in coordination names 456, 462 of 'ato' and 'ito' ligands 444 '(mesyloxy)-' 276 in ester names 159, 270 of bridge ligands 454 '(met)', ligand-name abbreviation 480(T) in hydrazide names 159, 314 of cationic ligands 453 'meta' 50, 68, 69 in hydrazone names 159, 330, 341 of neutral ligands 451 'metaboric acid' 254 in oxime names 159, 329, 340 with η descriptors 440 metal atoms, in heteromonocycles 76 in polymer names 467, 531, 534 with κ descriptors 438 metallocenes 459 multiplying affixes 539 general naming 15 element names 543(T) 'stereoisomer' 572, 591 hydrocarbon-chain names 55 stereodescriptors 592 modifying syllables 6, 541 in acid halide names 285, 289, 290 'metallocenophane' 460 molecular-skeleton parent names, see parent in amide names 299, 304, 306, 307 metallorganic compounds, see organometal- names in ester names 270, 273 lic compounds molecular-skeleton parents (see also parent in fused polycycles with replacement metal–metal bonds, see bond descriptor in structures) names 115 coordination names bridged fused polycycles 123ff. in fusion names 97, 99, 101 metals, definition 433 carbomonocycles 67ff. in heterochain names 62ff. metal-substituent prefixes 436, 463 collection 55ff. in heteromonocycle names 76, 82, 83f. 'metanilic acid' 492 conjunctive nomenclature 30 in hydrazide names 314, 317 'metaphosphate' 244 definition 6 in hydroperoxide names 355 'metaphosphimic acid' 244 determination 41 in polyborane names 397 'metaphosphite' 244 double-bond isomers 547 in semitrivial fusion names 89(T) 'metaphosphoric acid' 244 fused polycycles 85ff. in spiropolycycle names 134 'metaphosphorous acid' 244 heterochains 61ff. in von Baeyer bridged-polycycle names 'metha-' 540(T) heteromonocycles 73ff. 118 'methacrylamide' 301 hydrocarbon chains 55ff. multiplicative nomenclature 32 'methacrylic acid'/ 'methacryloyl-' 204 indicated H atom 547 multivalent substituents '(methanamine)', ligand name 452(T) numbering 49 multiplicative nomenclature 32, 33 'methane, monoprotonated' 170 ring assemblies 141ff. polycations 185 'methanetetrayl-' 57, 146 saturated or partially saturated 36 polymer names 531 'methan(o)-', bridge name 127(T) spiropolycycles 133ff. polyradicals 167 '()', ligand name 452(T) von Baeyer bridged polycycles 117ff. prefixes 34 (T) 'methanone' 337 'mono-' 50, 539, 540(T) prefixes for ester names 270, 273 '(methanoxymethan(o))-', bridge name 127(T) 'monoanhydride with…' 260, 262 'β-muramic acid' 495 'methen(o)-', bridge name 125, 127(T) monocycles, stereodescriptors 573 'myo-inositol' 509 '(methioninato)', ligand name for abbrevia- mononuclear substituents, prefixes 145 'myrcene' 520 tion 480(T) monosaccharide names, semisystematic 'myristic acid'/ 'myristoyl-' 204 'methionine'/ 'methionyl-' 211, 490 496ff. 'methoxide' 191 monosulfides and analogs 419f. 'methoxy' monosulfones and analogs 419f. ' 15N ' 599(T) ligand name 438, 442(T) monosulfoxides and analogs 419f. N compounds 371 radical name 164 monoterpenes 520 seniority 26(T) 'methoxy-' 18(T) '[monothiosulfato(2–)]' , ligand name N-heterochains 372 alcohols 351 445(T) N-heterocycles 371 esters 275, 277 'morphinan' 488 N-oxoacids 237 ethers 412 'morpholine' 75 salts 237 '-methoxy-' 'morpholino-' 76 seniority 21(T) esters 275, 276 'morpholinyl-' 76 name interpretation 13, 15 'methoxyl' 164 'MP ', stereodescriptor 572 'NamExpert' 537 'methoxylium' 177 'muco-inositol' 509 naming '-methyl-' mu descriptor, see µ descriptor general procedure 13 amides 303, 305 multiplication numbers, see multiplying structure analysis 2 carboxylic acids 217 affixes naming of the nonsenior central atom 465 C-oxoacids 233 multiplicative names 'naphthacene' 89(T) esters 275, 276 acyclic ethers 412 '' 89(T) imines 368 acyclic monosulfones, monosulfoxides, 'naphthalene-2-NNO-azoxybenzene' 374 ketones 335 monosulfides, and analogs 420 'naphthaleno-', bridge name 127(T), 128 parent-substituent name 157 definition 6 'naphthamide' 301 '-methyl-' 601 esters 270 'naphthionic acid' 223 'methyl alcohol' 347 multiplying affixes 539 'naphth(o)-' 89(T), 102, 541

624 Index

'naphthoic acid'/ 'naphthoyl-' 205 affix in S-, Se-, and N-oxoacid names 238 in spiropolycycles 548 'naphthol' 347 '(nitrosoamino)-' 240 interior atoms of fused polycycles 'naphthoquinone' 334 nitrosolic acids 329 CA 110 'naphthyl-' 88 'nitrosyl' IUPAC 95 '-naphthylene' 89(T) acid halides 290 isotopically modified compounds 51 'naphthyridine' 93(T) ligand name 438, 452(T) CA 601 '(napy)', ligand-name abbreviation 480(T) nitrosyls 434 molecular-skeleton parents 49 natural products, lit. 536 'nitrous acid' 238 multivalent substituents in multiplicative '(nbd)', ligand-name abbreviation 480(T) nitrous acids, seniority 21(T) nomenclature 33, 34(T) negatively charged structure component, 'nitroxide' 163 oximes 329, 340 transformation convention in the 'nitryl', acid halides 290 parent substituents 49 CIP system 564, 584 '(nmp)', ligand-name abbreviation 480(T) polymers consisting of structural repeat- 'neo-' 523f. 'Nomenclator' 537 ing units 531 'neo-inositol' 509 nomenclature software 1, 537 radical cations 200 'neopentane' 57 nomenclature terms 3 ring assemblies 142 'neopentyl-' 57 nomenclature type 29 Si-containing heteromonocycle names 84 'nerol' 521 general naming 14 spiropolycycles 134, 136 'nerolidyl-' 58 'nona-' 540(T) steroids 516 'neryl-' 58 nondetachable name parts 541 terpenes 520 'α-neuraminic acid' 495 nondetachable prefixes, see modifying von Baeyer bridged polycycles 118 N-glycosides 505, 510 syllables numerical prefixes, see multiplying affixes '(nia)', ligand-name abbreviation 480(T) nonmetal as central atom 435 numerical syllables 'niacin' 528 nonsenior central atom, naming 465 hydrocarbon-chain names 55 'nicotinaldehyde' 331 nonstandard amino acid 492 hydrocarbon names 539, 540(T) 'nicotinamide' 301 nonstandard valences 593 '(nicotinamide)', ligand name for abbrevia- unexpressed 593 tion 480(T) nontetraligant structure components 561, 584 'o', see 'ortho' 'nicotinic acid'/ 'nicotinoyl-' 205 'nor-' 'O', nucleoside abbreviation 511 'ninhydrin' 351 alkaloids 489 ' 17O ' 599(T) 'nitramide' 306 nondetachable name part 541 O compounds 409 'nitrate' 190, 238, 271 steroids 517 seniority 27(T) '(nitrato)', ligand name 445(T) triterpenes 523f. O-heterochains (see also peroxides and 'nitrato-' 240, 277 '(norbornadiene)', ligand name for abbrevia- polyoxides) 411 'nitrene' 163 tion 480(T) O-heterocycles 409 '-nitrene' 164 'norbornane' 520 '-(o)ate' 'nitric acid' 238 'norleucine'/ 'norleucyl-' 211, 212, 491 acid anion (salt) 190, 220, 227, 234, 249 nitric acids, seniority 21(T) 'norspermidine' 364 esters 270, 273, 279 'nitride' 290 norsteroids 517 '-ocane', Hantzsch–Widman names 78(T) 'nitrido', ligand name 443(T) 'norvaline'/ 'norvalyl-' 211, 212, 491 IUPAC 78(T) '-nitrid(o)-', infix in P- and As-oxoacid 'novi-' 539 '-ocene', metallocene 459 names 245 '(nta)', ligand-name abbreviation 446, 480(T) '-ocin(e)', Hantzsch–Widman names 78(T) '-nitrilato', ligand name 444 nucleic acids 510, 514 'octa-' 540(T) '-' 24(T), 322 nucleoside bases 510 'octahedro' 467 'nitrile imine' 195 nucleoside esters 512 'octi-' 539 nitrile oxides 322 nucleosides 510 'octose' 496 nitriles 321, 321(T) nucleotides 510 '-odialdose' 496 carbohydrate acids 498 nuclide symbols '-odiulose' 496 functional-class names 322 by CA 599(T), 601 '(oep)', ligand-name abbreviation 480(T) of peptides 492 by IUPAC 599(T), 600 '-ofuranose' 498 seniority 24(T) numbering '-ofuranoside' 504 'nitrilio-' 182 'added' indicated H atom '-ofuranosyl-' 504 '-nitrilium' (+ E+) 173 in ring assemblies 551 '-ohydrazide' 314 nitrilium ylide' 196 in spiropolycycles 551 '-ohydrazonoyl-', acyl prefix 217 'nitrilo-' 322 bridged fused polycycles 129 '-ohydroximoyl-', acyl prefix 217 amines 360 carbohydrates 494 '-oic acid' 20(T), 203 bridge name 127(T) carbomonocycles 67 alkaloids 489 imines 368 cations 170f., 179 carotenoids 524 multivalent substituent 34(T) choice (seniority) in von Baeyer bridged '-oic acid anhydride' 23(T) '(nitrilotriacetato)', ligand name for abbre- polycycles 119 '-oic acid ester' 23(T) viation 446 compulsory 50 '-oic acid hydrazide' 24(T) 'nitrilotriacetic acid' 32 fused polycycles '-(o)ic acid hydrazide' 314 'nitrite' 190, 238, 271 with fusion names 107ff. '-(o)ite' '(nitrito-κN)', ligand name 445(T) with replacement names 115 acid anion (salt) 190, 249 '(nitrito-κO)', ligand name 445(T) with semitrivial or trivial names 86 esters 270, 273, 279 'nitro-' 18(T), 240, 276, 306, 378 general naming 14 '-ol' 25(T), 347 'aci-nitro-' 18(T), 329, 340, 378 heterochains 62ff. carotenoids 524 '(nitroamino)-' 240 heteromonocycles '-olactam' 295 compounds, see N compounds with Hantzsch–Widman names 77 '-olactim' 295 nitrogen-containing oxoacids, see N-oxo- with replacement names 82 '-olactone' 268 acids with trivial names 75 '-olane', Hantzsch–Widman names 78(T) nitrolic acids 329 hydrazones 330, 341 '-olate' 191 'nitrone' 363, 369 hydrocarbon chains 55 '-olato', ligand name 444 'nitronic acid' 329, 340 identical structure units, multiplicative '-ole', Hantzsch–Widman names 78(T) '(nitrooxy)-' 240 nomenclature 33 'oleamide' 301 'nitroryl-' 238, 329, 340, 379 indicated H atom 'oleanane' 523 '-nitroryl-' 18(T) in bridged fused polycycles 548ff. 'oleic acid'/ 'oleoyl-' 204 'nitrosamide' 306 in cyclic molecular-skeleton parents 548 '-olene' 77 '-' 18(T), 240, 276, 306, 339, 378 in ring assemblies 548 'olide' names 268

625 Index

'-olidine', Hantzsch–Widman names 78(T) pseudoketones 339 fusion side 103 oligonucleotides 512 S-, Se-, and Te-heterocycles 416 multiple occurrence 99, 105 oligosaccharides 505 '(oxidoamino)-' 363 names 99ff. '-oline' 74, 77 '(oxidoimino)-' 363 nonsenior 95 '-olone' 295, 334 'oximato', ligand name 444 senior (choice) 89(T), 91(T), 98 '-onane', Hantzsch–Widman names 78(T) 'oxime' 329, 340 parent-component letters 103 IUPAC 78(T) oximes order 106 '-onato', ligand name 444 of acid halides 325 parent compounds, see parent structures '-one' 25(T), 333ff. of acids 23(T) parent , see parent structures carotenoids 524 of aldehydes 24(T), 325 parent names '-onia-' 19(T), 543(T) seniority 24(T) bridged fused polycycles 123ff. cation by ring formation 179 of amides 325 carbomonocycles 67ff. cation by skeletal bonding 179 of carboxylic acids 325 collection 55ff. cation (+ E+) 171 of ketones 24(T), 333 definition 6 polycation 184 seniority 24(T) for identical structure units, multiplicative '-onia…yl-', cation (prefix) 182 of monosaccharides 503 nomenclature 32 '-onic acid' 497 pseudoesters 267 fundamental fused carbopolycycles 89(T) '-onin(e)', Hantzsch–Widman names 78(T) 'oxindole' 342 fundamental heterocycles 91(T) '-onitrile' 322 'endo-oxirano-', bridge name 128 fused polycycles 85ff. optical rotation 572 'oxo', ligand name 442(T) general naming 14 '-opyranose' 498 'oxo-' heterochains 61ff. '-opyranoside' 504 acid halides 288 heteromonocycles 73ff. '-opyranosyl-' 504 aldehydes 24(T), 327 hydrocarbon chains 55ff. '-oranyl-', mononuclear substituents 145 amides 303 ring assemblies 141ff. '-oranylidene-', mononuclear substituents 145 carboxylic acids 203, 205 seniority 41 '-oranylidyne-', mononuclear substituents 145 esters 275, 278 spiropolycycles 133ff. organometallic compounds 433, 458 ketones 25(T), 334ff. substitutive nomenclature 29 central-atom names 436 prefix 156 von Baeyer bridged polycycles 117ff. element names 543(T) radicals 163 parent radical, choice (seniority) 167 seniority 19(T), 27(T), 434 '(oxoalkanido)', ligand names 450 parents, see parent structures stereodescriptors 470, 582 oxocarboxylic acids 208f. parent structures orientation of fused polycycles 107 '(1-oxoethane-1,2-diyl)-', multivalent sub- choice (seniority) 41 'ornithine'/ 'ornithyl-' 211, 491 stituent 34(T) definition (molecular-skeleton parents, 'orotic acid' 510 'oxonio-' 182 functional parents, stereoparents) 'orotidine' 511 'oxonium' 6 'ortho' 50, 68, 69 cation 170 parent-substituent names 'orthoacetate' 413 ligand name 453(T) alphabetical order 53 orthocarboxylic acids 23(T) 'oxonium ylide' 197 definition 7 esters 271, 273, 411 'oxy-', multivalent substituent 34(T) functional-class nomenclature 39 'orthosulfurous acid' 238 '-oxy', radical name 164 general naming 14 osazones 24(T), 325, 330, 333, 341 '-oxy-' 18(T) seniority 41 of carbohydrates 503 esters 274ff. substitutive nomenclature 29 '-ose' 496ff. ethers 412 parent substituents '-oseptanose' 498 S-, Se-, Te-, and N-oxoacids 240 choice (seniority) 153, 154 '-oseptanoside' 504 '[oxybis(methylene)]-', multivalent substitu- definition 7 '-osulose' 496 ent 34(T) numbering 49 '-osyl-' 504 '(-oxycarbonyl)-' 23(T) 'partial ', CA stereodescriptors until 1999 574ff. 'ovalene' 90(T) '(oxydicarbonyl)-' 23(T), 263 Pb compounds 403, 458 '(ox)', ligand-name abbreviation 480(T) compounds, see O compounds seniority 27(T) 'oxa-' 541, 543(T) '-oxyl' 165 stereodescriptors 582, 585 'oxalacetic acid'/ 'oxalacetyl-'/ 'oxalaceto-' 209 'oxytocin' 493 Pb-heterochains 405 'oxalaldehydic acid' 213 '-oyl', acid halide suffix 286(T) Pb-heterocycles 403 '(oxalato)', ligand name for abbreviation '-oyl-', acyl prefix 204, 205 '(pc)', ligand-name abbreviation 480(T) 480(T) '-oyl halide' 24(T), 286(T) '(1,2-pdta)', ligand-name abbreviation 480(T) 'oxalic acid'/ 'oxalyl-'/ 'oxalo-' 204 ozonides, lit. 536 '(1,3-pdta)', ligand-name abbreviation 480(T) 'oxalyl-' 207 'penta-' 540(T) 'oxamic acid'/ 'oxamoyl-' 214 'pentacene' 90(T) 'oxamide' 301 'p', see 'para' 'pentaerythritol' 347 'oxanthrene' 91(T) 'P ' 'pentafulvalene' 141 'oxayohimban' 488 assignment of configuration 560 'pentalene' 89(T) 'oxazole' 79 citation in names 571 '(N,N,Nʹ,Nʹʹ,Nʹʹ-pentamethyldiethylenetri~ 'oxazolidine' 79 ' 32P ' 599(T) amine)', ligand name for abbre- 'oxidane' 412 P compounds 383 viation 480(T) oxidation number 6, 434 seniority 26(T) 'pentaphene' 90(T) 'oxidato', ligand name 444 P-heterochains 384 'pentose' 496 'oxide' 36 P-heterocycles 383 pentoses 494 amine N-oxides 363 P-oxoacids 243 '(tert-pentyl)-' 57 nonstandard valences 594 salts 243, 249 peptides 299, 492, 535 pseudoketones 339 seniority 22(T) biologically active 493 S-, Se-, and Te-heterocycles 416 'palmitamide' 301 not replacement names 61 oxides 'palmitic acid'/ 'palmitoyl-' 204 stereodescriptors 571 of aldehydes 326 'pamidronic acid' 250 peptidoglycans, see IUPAC of amines 363 'pantothenic acid' 214, 492, 526 'peracetic acid' 219 of ketones 333 'para' 50, 68, 69 peracids, see peroxy acids of nitriles 322 parent cation, choice (seniority) 185 'perbenzoate' 192 of polymers 531 parent component 'perbenzoic acid' 219 'oxido-' 36 benzoheteromonocycle 96 'perchlorate' and analogs 237 nonstandard valences 594 definition 6 '(perchlorato)', ligand name 445(T)

626 Index

'perchloric acid' and analogs 237 seniority 25(T) 'phosphinidyne-' 'perchloryl-' 18(T), 429 'phenomercurine' 91(T) bridge name 127(T) 'performic acid' 231 'phenophosphazine' 93(T) P-heterochains 385 'perhydro-' '10H-phenoselenazine' 94(T) P-oxoacids 247 bridged fused polycycles 128 '10H-phenotellurazine' 93(T) 'phosphinimine' 368, 386 fused polycycles 86, 112, 115 '10H-phenothiarsine' 92(T) 'phosphinimyl-' Hantzsch–Widman names 77, 78(T) '10H-phenothiazine' 94(T) P-heterochains 386 heteromonocycles 75 '10H-phenoxantimonin' 92(T) P-oxoacids 247, 248 '1H-perimidine' 93(T) '10H-phenoxaphosphine' 92(T) '-phosphinimyl-' and analog 'periodinane' 432 '10H-phenoxarsine' 92(T) acid halides 292 'periodyl-' 429 'phenoxaselenin' 92(T) amides 308 peripheral numbering, fused polycycles 108 '10H-phenoxasilin' 92(T) esters 277 'peroxide' 27(T), 258, 260, 410 '10H-phenoxastibinin' 92(T) 'phosphinimylidene-', P-oxoacids 247, 248 peroxides 38, 410 'phenoxatellurin' 92(T) 'phosphinite' 244 '-peroxo-', infix in names 'phenoxathiin' 92(T) 'phosphino', ligand name 438, 443(T) of carboxylic acids 218 '10H-phenoxazine' 94(T) 'phosphino-' of C-oxoacids 230 'phenoxide' 191 P-heterochains 64, 385 of P- and As-oxoacids 245 'phenoxy' P-oxoacids 247, 248 of sulfonic acids and analogs 226 ligand name 442(T) '-phosphino-' and analog '-peroxoic acid' 19(T), 218 radical name 165 acid halides 292 '-peroxothioic acid' 218 'phenoxy-' 18(T) amides 308 'peroxy', ligand name 438, 443(T) alcohols 351 esters 277 'peroxy-', affix in names esters 277 'phosphinoline' 91(T) of polynuclear C-oxoacids 232 ethers 412 '4H-phosphinolizine' 91(T), 93(T) of polynuclear P- and As-oxoacids 249 'phenyl', ligand name 438, 442(T) 'phosphinothioyl-' and analogs of polynuclear S- and Se-oxoacids 239 'phenyl-' 68, 148 P-heterochains 386 of S-, Se-, and N-oxoacids 238 '(phenylalaninato)', ligand name for abbre- P-oxoacids 247, 248 '-peroxy-' 410 viation 480(T) '-phosphinothioyl-' and analogs peroxy acid esters 'phenylalanine'/ 'phenylalanyl-' 211, 491 acid halides 292 formal dichalcogenides 418 '(phenylazo)', ligand name 443(T) amides 308 formal peroxides 410 '(phenylazo)-' 373 esters 277 peroxy acids 'phenyldiazenol' 375 'phosphinothioylidene-' and analogs carboperoxoic acids and analogs 218 'phenyldiazoic acid' 375 P-heterochains 386 C-oxoacids 230 'phenylene-' P-oxoacids 247, 248 formal acid halides 287, 289, 291 multivalent substituent 34(T) 'phosphinothioylidyne-' and analogs formal amides 299, 304, 306, 307 prefix 68, 148 P-heterochains 386 formal anhydrides 258, 260, 262 '-phenylene' 89(T) P-oxoacids 247 formal hydroperoxides 355 'phenylenediamine' 361 'phosphinous acid' 244 P- and As-oxoacids 245 '(phenylsulfonyl)', ligand name 442(T) '-phosphinous acid' 22(T), 244 seniority 19(T) 'phloroglucin' 351 phosphinous acids, seniority 22(T) sulfonoperoxoic acids and analogs 226 'phorbine' 529 'phosphinoyl-' 247 peroxycarboxylic acids, see carboperoxoic 'phosgene' 230 'phosphinyl', ligand name 442(T) acids and analogs 'phospha-' 543(T) 'phosphinyl-' 'peroxydicarbonic acid' 21(T), 232 'phosphane' 63, 385 P-heterochains 386 'peroxydiphosphoric acid' 249 'phosphanthrene' 91(T) P-oxoacids 247, 248 'peroxydisulfuric acid' 240 'phosphanthridine' 91(T) '-phosphinyl-' and analog 'peroxypropionic acid' 219 'phosphate' 190, 243, 271 acid halides 292 peroxysulfonic acids, see sulfonoperoxoic phosphate residue, in nucleotides 511f. amides 308 acids and analogs phosphates, of nucleosides 510, 512 esters 277 'perylene' 90(T) '[phosphato(3–)]', ligand name 445(T) 'phosphinylidene-' 'peryl(o)-' 90(T), 102 phosphazines 24(T), 325, 330, 333, 341 P-heterochains 386 'Ph', ligand-name abbreviation 480(T) 'phosphenate' 244 P-oxoacids 247, 248 phanes 117, 123 'phosphenic acid' 244 'phosphinylidyne-', P-oxoacids 247 phantom atoms, see dummy atoms phosphenic acids, seniority 22(T) 'phosphite' 190, 243, 271 '(phe)', ligand-name abbreviation 480(T) 'phosphenite' 244 'phospho-' '(phen)', ligand-name abbreviation 480(T) 'phosphenous acid' 244 esters 277 'phenacyl', radical name 161 phosphenous acids, seniority 22(T) P-heterochains 386 'phenacyl-', prefix 335, 337 'phosphetene' 77 P-oxoacids 247 '1H-phenalene' 89(T) 'phosphide' 188 '(phosphoamino)-' 308 'phenanthrazine' 94(T) 'phosphido', ligand name 443(T) 'phospholipid' 271 'phenanthrene', exception of numbering 'phosphinate' 243 'phosphonate' 243 89(T), 112 '1H-phosphindole' 91(T) '[phosphonato(2–)]', ligand name 445(T) 'phenanthridine' 93(T) 'phosphindolizine' 91(T), 93(T) 'phosphonic acid' 243, 244 'phenanthro-' 89(T), 102 '' 26(T), 63, 385 '-phosphonic acid' 22(T), 244 'phenanthrol' 347 '(phosphine)', ligand name 452(T) phosphonic acids, seniority 22(T) 'phenanthroline' 93(T) 'phosphine imide' 26(T), 367, 368, 386 'phosphonio-' 182 'phenanthrone' 334 'phosphine oxide' 26(T), 386 'phosphonite' 243 'phenanthryl-' 88 'phosphine sulfide' and analogs 26(T), 386 '[phosphonito(2–)]', ligand name 445(T) 'phenarsazine' 93(T) 'phosphinic acid' 243 'phosphonitrile' 290 'phenazine' 91(T), 93(T) '-phosphinic acid' 22(T), 244 'phosphonitrile amide' 291, 307 '-phene' 90(T) phosphinic acids, seniority 22(T) 'phosphonium' 'phenethyl-' 69 'phosphinico-' 22(T), 153, 248, 386 cation name 170, 175 'phenethyl alcohol' 351 'phosphinidene', ligand name 443(T) ligand name 453(T) 'phenetidine' 364 'phosphinidene-' 'phosphonium ylide' 196 'phenetole' 414 bridge name 127(T) 'phosphono-' 'pheno-' 92(T) P-heterochains 385 esters 277 'phenol' 347 P-oxoacids 247, 248 P-heterochains 386 phenols 347 'phosphinidenio-' 182 P-oxoacids 22(T), 247

627 Index

'phosphono-' (cont.) polyanions 194 hydrocarbon-chain substituents 55ff., 146 prefix 153 'polyarsenamide' 307 locants 50, 51 '(phosphonoamino)-' 308 polyboranes 397 mononuclear substituents 145 'phosphononitridyl-' polycarbonates 531 multiplying affixes 539 P-heterochains 386 polycarboxylic acids 205 multivalent substituents 34(T) P-oxoacids 247 polycations 184 order in heading parents 155 'phosphononitrylidene-', P-oxoacids 247 polycycles, fused, see fused polycycles ring-assembly substituents 142, 152 'phosphonous acid' 243 polyesters 531 spiropolycycle substituents 134, 138, 149, '-phosphonous acid' 22(T), 244 polyhedral symbols 582(T) 150 phosphonous acids, seniority 22(T) coordination compounds 470, 582 substitutive nomenclature 29 'phosphonoyl-' 248 definition 7 subtractive 37, 541 'phosphorane' 26(T), 63, 196, 385 polymers 531 von Baeyer bridged-polycycle substituents 'phosphoranyl-', P-heterochains 385 CA indexes 531 120, 149, 150 'phosphoric acid' 243, 244 coordination compounds 467, 531 'pregnane' 516 phosphoric acids, seniority 22(T) general naming 13 'prenols' 523 'phosphoric trihydrazide' 317 not replacement names 61 'prenyl-' 59 'phosphorin' 78(T) siloxanes 531 primary amines 360 'phosphorinane' 78(T) polynuclear coordination compounds 433, primary attached component, see attached '[phosphorofluoridato(2–)]', ligand name 463ff. component 445(T) stereodescriptors 592 priming convention, priority numbers 583 'phosphoroso-' polynuclear C-oxoacids 232 principal chain esters 277 polynuclear P- and As-oxoacids 249 C compounds 426 P-heterochains 386 polynuclear S- and Se-oxoacids 239 definition 7 P-oxoacids 247 polynucleotide 'complex' 535 determination of molecular-skeleton '(phosphorosoamino)-' 308 polynucleotides 514, 535 parents 42, 46 'phosphorous acid' 243 modified 514 principal group phosphorus compounds, see P compounds polyoxides 38, 410 assignment of 'added' indicated H atom phosphorus-containing oxoacids, polypeptides, see peptides 553f. see P-oxoacids 'polyphosphoramide' 307 assignment of indicated or 'added' indi- 'phosphoryl-' 248 polyphosphoric acids 512 cated H atom 552 'phosphoryl' names 291 polyradicals 167 choice (seniority) 13, 19(T) 'phthalaldehyde' 328 polysaccharides 507, 508, 535 definition 7 'phthalaldehydic acid' 213 'polyselane' 418 determination of molecular-skeleton 'phthalamide' 301 polyspiro structures 137 parents 41 'phthalate' 192 '' 418 in conjunctive nomenclature 30 'phthalazine' 93(T) polysulfides 38 locants 50 'phthalic acid'/ 'phthaloyl-' 205 polysulfides and analogs 417 no indicated H atom 553 'phthalic anhydride' 258 polysulfones 38 priority, see seniority 'phthalide' 268 polysulfones and analogs 416 priority letters 7, 560 'phthalimide'/ 'phthalimido-' 296 polysulfoxides 38 priority numbers 7, 470, 582 '29H,31H-phthalocyanine' 529 polysulfoxides and analogs 416 'prismane' 118 '1H-phthaloperine' 94(T) 'polytellane' 418 '(pro)', ligand-name abbreviation 480(T) 'phylloquinone' 528 polyurethanes 531 '(prolinato)', ligand name for abbreviation 'phythyl-' 58 'porphine' 529 480(T) 'phytol' 351, 522 '21H,23H-porphyrazine' 529 'proline'/ 'prolyl-' 211, 491 'picene' 90(T) 'porphyrin' 527, 529 'propa-' 540(T) 'picolinic acid'/ 'picolinoyl-' 208 'porphyrinogen' 529 'propargyl-' 58 'picrate' 193 porphyrins 529 'propiolamide' 301 'picric acid' 347 metal complexes 529 'propiolic acid'/ 'propioloyl-' 204 pilot atom, obsolete in the CIP system 561 position of locants in index names 2, 49 'propionamide' 301 'pimelic acid'/ 'pimeloyl-' 204 'potassio-' 436 'propionic acid'/ 'propionyl-' 204 'pinacol' 347 '(ppIX)', ligand-name abbreviation 480(T) 'propoxide' 191 'pinadiene' 521 'pR ' 561 'propoxy', radical name 165 'pinane' 520 prefixes 'propoxy-' 18(T) '(pip)', ligand-name abbreviation 480(T) alphabetical order 53 alcohols 351 'piperazine' 74 anion substituents 193 esters 277 'piperidine' 74 bridged fused-polycycle substituents 128, ethers 412 'piperidino-' 76 149, 150 '-propoxy-', esters 275 'piperidyl-' 76 carbomonocycle substituents 67, 148 'propriophenone' 337 'piperonal' 331 carbonyl-containing substituents and 'propylene-' 56, 58 'piperonylic acid'/'piperonyloyl-' 209 analogs 156 '(1,2-propylenediaminetetraacetato)', ligand 'piperylene' 58 cation substituents 182 name for abbreviation 480(T) 'pivalic acid'/ 'pivaloyl-' 204 composite substituents 153 '(1,3-propylenediaminetetraacetato)', ligand planar chirality, see chirality axis, stereogenic composite substituents, alphabetical order name for abbreviation 480(T) axis 53 'protocatechuic acid'/ 'protocatechuoyl-' 209 'pleiadene' 89(T) compound classes 19ff.(T) 'proton' 169, 187 'plumba-' 543(T) compulsory 18(T) '(protoporphyrinato IX)', ligand name for '' 27(T), 63, 405 conjunctive nomenclature 30 abbreviation 480(T) 'plumban(o)-', bridge name 127(T) definition 7 'pS ' 561 plumbathianes 65 for identical structure units, multiplicative pseudo 'plumbyl-' 64, 405 nomenclature 32 definition 7 'plumbylene-' 405 functional-class nomenclature 39 pseudoacid halides 'plumbylidyne-' 405 fused-polycycle substituents 87, 112, 115, P- and As-heterochains 385 'PM ', stereodescriptor 572 149, 150 P- and As-heterocycles 384 '(pmdien)', ligand-name abbreviation 480(T) general naming 13 pseudoacids '(pn)', ligand-name abbreviation 453, 480(T) heterochain substituents 62ff., 147 definition 7 'poly-' 531 heteromonocycle substituents 75, 77, 82, P- and As-heterochains 385 polyamides 299, 531 84, 150 P- and As-heterocycles 384

628 Index pseudoalcohols 350 '2H-pyran' 73, 92(T) 'radical ion(1–)' 199, 200 boranes 400 'pyranthrene' 90(T) radical ions 199 definition 7 'pyrazine' 74, 92(T) radicals 161 Ge-, Sn-, and Pb-heterochains 406 '1H-pyrazole' 74, 92(T) definition 7 Ge-, Sn-, and Pb-heterocycles 404 'pyrazolidine' 74 seniority 19(T) general naming 13, 25(T) '' 89(T) radicofunctional names, see functional-class N-heterochains 374 'pyridazine' 75, 93(T) names N-heterocycles 372 'pyridine' 74, 92(T) 'raffinose' 506 P- and As-heterochains 386 '(pyridine)', ligand name 438, 452(T) ratio P- and As-heterocycles 384 'pyridinio-' (prefix) 182 in anhydride names 262 polyboranes and B-heterocycles 399 'pyridinyl', ligand name 438, 442(T) in coordination names 456, 462 Sb- and Bi-heterochains 393 'pyrido-' 92(T), 102, 541 in ester names 273 Sb- and Bi-heterocycles 392 'pyridone' 334 in salt names 233, 249 pseudoamides 'pyridoxal' 526 'Red Book' 7, 433 definition 7 'pyridoxamine' 526 reference atom, in monosaccharides 499 pseudoamides (see also 'unexpressed 'pyridoxine' 351, 526 reference center, for CA stereodescriptors amides') 'pyridoxol' 351, 526 until 1999 573ff. general naming 13, 25(T) 'pyridyl-' 76, 88 reference plane ketones 335 '' 74, 93(T) for CA stereodescriptors until 1999 573ff. N-heterochains 374 'pyrimido-' 93(T), 102 in bicyclo[X.Y.Z ]alkanes 573 'pseudoasymmetric' axis 559, 561 'pyrindine' 86 in meso ring structures 573 'pseudoasymmetric' center 559, 560, 573 'pyrocarbonic acid' 232 in monocycles and ring assemblies 573 pseudoatom, stereodescriptors 591 'pyrocatechol' 347 in stereogenic double bond 561 pseudoesters 'pyrogallol' 351 'rel ' (acyloxy) prefixes 350 'pyroglutamic acid' 214 citation in names 572 definition 7, 267 'pyrophosphoric acid' 249 meso compounds 572 Ge-, Sn-, and Pb-heterochains 406 'pyrosulfuric acid' 239 replacement names Ge-, Sn-, and Pb-heterocycles 404 'pyrosulfurous acid' 239 acyclic ethers 411 general naming 13 '1H-pyrrole' 74, 92(T) acyclic monosulfones, monosulfoxides, hydroxylamines 267 'pyrrolidine' 74 monosulfides, and analogs 420 N-heterochains 374 'pyrrolidone' 296, 334 amides 299 N-heterocycles 372 'pyrroline' 74 amines 359 oximes 267 '1H-pyrrolizine' 93(T) anhydrides 258 P- and As-heterochains 385 'endo-pyrrolo-', bridge name 128 B-heterochains 401 P- and As-heterocycles 384 'pyruvamide' 301 cations 171, 179 polyboranes and B-heterocycles 399 'pyruvic acid'/ 'pyruvoyl-' 209 definition 7 Sb- and Bi-heterochains 393 'pyrylium' 179 esters 269 Sb- and Bi-heterocycles 392 '(pyz)', ligand-name abbreviation 480(T) heteroatom syllables 543(T) pseudohydroperoxides '(pz)', ligand-name abbreviation 480(T) heterochains 61 general naming 13, 25(T) hydrazides 314 hydroperoxides 356 ketones 335 N-heterochains 374 '(qdt)', ligand-name abbreviation 480(T) N-heterochains 375 N-heterocycles 372 'quater-' 141, 539 not for steroids 517 P- and As-heterocycles 384 quercitols 509 O-heterochains 411 polyboranes and B-heterocycles 399 '(quin)', ligand-name abbreviation 480(T) P- and As-heterochains 388 Sb- and Bi-heterocycles 392 'quinazoline' 93(T) polycations 184 pseudoimines 367 '1H-quindoline' 94(T) porphyrins 529 definition 7 '1H-quinindoline' 94(T) S-, Se-, and Te-heterochains 420 P- and As-heterocycles 384 'quino-' 93(T), 102 Sb- and Bi-heterochains 394 S-, Se-, and Te-heterocycles 416 'quinoline' 93(T) seniority 61 Sb- and Bi-heterocycles 392 '4H-quinolizine' 93(T) Si-, Ge-, Sn-, and Pb-heterochains 407 pseudoketones 'quinolone' 296, 334 replacement nomenclature (see also replace- acyl prefixes 335, 337 'quinolyl-' 88 ment names) additive names 338 '-quinone' 334 fused polycycles 95, 114 boranes 400 'quinovose' 503 heteromonocycles 81f. definition 7 'quinoxaline' 93(T) prerequisites for heterochains 61 general naming 13, 25(T) 'quinque-' 539 Sb-, Bi-, Ge-, Sn-, or Pb-heteromono- N-heterochains 374 'quinuclidine' 118 cycles 79 N-heterocycles 372 Si-containing fused polycycles 95, 114 P- and As-heterochains 267, 386 spiropolycycles 134 P- and As-heterocycles 384 'r', stereodescriptor 573 von Baeyer bridged polycycles 118 polyboranes and B-heterocycles 399 'R ' 'resorcinol' 347 Sb- and Bi-heterochains 393 assignment of configuration 560 'retinal' 522 Sb- and Bi-heterocycles 392 CA stereodescriptors until 1999 573ff. 'retinoic acid' 522 Si-, Ge-, Sn-, and Pb-heterochains 406 citation in names 571 retinoids 522 Si-, Ge-, Sn-, and Pb-heterocycles 404 stereogenic central atom, determination 'retinol' 522, 526 pseudopeptide bond 492 583 'retro' names, carotenoids 525 pseudoprefixes 36, 339 'R*' 'rhamnose' 503 'pseudouridine' 511 by IUPAC 572 'rhodanine' 309 'psicose' 495 CA stereodescriptors until 1999 573ff. 'rhodopin' 525 'pteridine' 93(T) 'rac', stereodescriptor 573 'rhodoxanthin' 525 'pteroic acid' 493 racemates, stereodescriptors 572 'ribo-' 494 'pteroylglutamic acid' 493 radical center 'riboflavin' 526 '(ptn)', ligand-name abbreviation 480(T) at characteristic group 163 '-ribonucleic acid' 514 '7H-purine', exception of numbering 93(T), at molecular-skeleton parents 161 'ribose' 494 112 at N atom 164 ring analysis 85 'putrescine' 364 at O atom or chalcogen analogs 164 ring assemblies 141 '(py)', ligand-name abbreviation 480(T) 'radical ion(1+)' 199, 200 'added' indicated H atom 551

629 Index

ring assemblies (cont.) of carboxylic acids and analogs 220 '-seleninyl', acid halide suffix 286(T) determination of molecular-skeleton of coordination anions 461 '-seleninyl-' 18(T), 225, 288, 421 parents 41 of coordination cations 456 'selenious acid' 238 indicated H atom 548 of C-oxoacids 233 selenious acids, seniority 21(T) multiplying affixes 539 of esters 278 'selenite' 238, 271 of benzene components 141 of P- and As-oxoacids 243, 249 selenium compounds, see Se compounds of carbomonocycles 141 of polynuclear coordination compounds selenium-containing oxoacids, see Se-oxo- of heteromonocycles with 'cyclo-' names 463 acids 141 of S-, Se-, Te-, and N-oxoacids 237f. 'seleno-', multivalent substituent 34(T) of Si-containing heteromonocycles 142 of silicic acids 253 '-seleno', radical name 164 stereodescriptors 573 of sulfonic acids and analogs 227 '-seleno-' 18(T), 225, 288, 421 with substituent names 141 polymers 531 selenoanhydrides, see anhydroselenides ring-assembly substituents 'salt with…' 189ff. '-selenol' 25(T), 347 of branched polyphenyls 152 'sarcosine' 214, 492 'selenolo-' 91(T), 102 prefixes 142, 152 'sarpagan' 488 '-selenonamide' 298(T) ring component, in conjunctive nomencla- saturated atom 'selenone' 333 ture 30 angular center in cyclic molecular-skel- '-selenonic acid' 21(T), 223 ring structure, transformation convention in eton parent 547 selenonic acids 223 the CIP system 563, 584 between two bivalent heteroatoms 547 seniority 20(T) 'Ring Systems Handbook' Sb compounds 391, 458 'selenonio-' 182 bridged fused polycycles 123 seniority 26(T) 'selenonium' 170 fused polycycles 85 Sb-heterochains 392 'selenono-' 21(T), 153, 223 heteromonocycles 73 Sb-heterocycles 391 'selenonyl', acid halides 290 ring assemblies 141 Sb-oxoacids 253 '-selenonyl', acid halide suffix 286(T) spiropolycycles 133 seniority 22(T) '-selenonyl-' 18(T), 225, 288, 421 von Baeyer bridged polycycles 117 Schiff bases 362, 368 'selenophene' 73, 91(T) 'RNA' 514 SciFinder® 1 'selenophene-2-yl-' 76 rotaxanes, lit. 536 'scyllo-inositol' 509 'selenothioacetic acid' 215 'RS ', stereodescriptor 572 '(sdta)', ligand-name abbreviation 482(T) '(selenothiocarboxy)-' 215 'rubicene' 90(T) Se compounds 415 '-selenothioic acid' 214 seniority 27(T) '9H-selenoxanthene', exception of number- Se-heterochains 416ff. ing 92(T) 'S ' Se-heterocycles 415 'selenoxo-' assignment of configuration 560 Se-oxoacids 237 acid halides 288 CA stereodescriptors until 1999 573ff. salts 237 aldehydes 24(T), 327 citation in names 571 seniority 21(T) amides 303, 305 stereogenic central atom, determination 'sebacic acid'/'sebacoyl-' 204 carboxylic acids 217 583 'sec-' 541 C-oxoacids 233 'S*' 'seco-' esters 275, 276, 278 by IUPAC 572 alkaloids 489 ketones 25(T), 334ff. CA stereodescriptors until 1999 573ff. nondetachable name part 541 prefix 156f. ' 35S ' 599(T) oligonucleotides 513 radicals 163 S compounds 415 steroids 517 '(selenoxomethyl)-' 24(T) seniority 27(T) triterpenes 524 'selenyl' S-heterochains 416ff. secondary amines 360 ligand name 438, 442(T) S-heterocycles 415 secondary bridges of von Baeyer bridged radical name 163 S-oxoacids 237 polycycles 118 'selenyl-' 25(T), 153, 347, 350 salts 237 secosteroids 517, 527 '(selenyloxy)-' 219 seniority 21(T) 'selane' 63, 223 'selinane' 576 'saccharin' 309 'selanyl-' 347 '-selone' 25(T), 333ff., 416 'saccharose' 505 'selena-' 543(T) '(selpuchrate)', incorrect ligand name for '(sal)', ligand-name abbreviation 480(T) '-selenal' 24(T), 327 abbreviation 482(T) '(salan)', ligand-name abbreviation 480(T) 'selenanthrene' 91(T) 'semicarbazide' 301, 316, 325 '(saldien)', ligand-name abbreviation 482(T) 'selenate' 238 'semicarbazido-' 305, 316 '(salen)', ligand-name abbreviation 482(T), 'selenazole' 79 'semicarbazone' 301, 325, 346 588 'selenazolidine' 79 semicarbazones 23(T), 24(T) '(salgly)', ligand-name abbreviation 482(T) '-selenenamide' 298(T) 'semicarbazono-' 316 '(salicylato)', ligand name for abbreviation '-selenenic acid' 21(T), 223 semicolons in sets of locants 49 480(T) selenenic acids 223 'semioxamazone' 326 'salicylic acid' 351 seniority 20(T) semioxamazones 24(T) 'salicylic acid'/ 'salicyloyl-' 209 'seleneno-' 21(T), 153, 223 semisystematic names, see semitrivial names 'salicylic alcohol' 349 '-selenenyl', acid halide suffix 286(T) semitrivial names, definition 8 '(salicylideneanilinato)', ligand name for 'selenic acid' 238 senior, see seniority abbreviation 480(T) selenic acids, seniority 21(T) senior chain '(salicylideneglycinato)', ligand name for 'selenide' 36 determination of molecular-skeleton abbreviation 482(T) anion 237 parents 42, 46 '(salpn)', ligand-name abbreviation 482(T) nonstandard valences 594 seniority (see also choice) 'salt' 189ff., 220, 227, 249, 278 pseudoketones 339 acid halides 285, 289, 290 '(saltn)', ligand-name abbreviation 482(T) 'selenido-' 36 amides 304, 307 salts nonstandard valences 594 amines 360 acetylides 458 pseudoketones 339 anhydrides 257 carbonyls 434 '2H-selenin' 74 'ate' names 543(T) lit. 536 '-seleninamide' 298(T) atoms in stereoisomers 566 neutral compounds MHx 442 '-seleninic acid' 21(T), 223 B-heterochains with replacement names nitrosyls 434 seleninic acids 223 401 of boric acids 254 seniority 20(T) carbocycles 426 of boronic and borinic acids 255 'selenino-' 21(T), 153, 223 carbonic and formic acids 21(T) of carbohydrate acids 498 'seleninyl', acid halides 290 carboxylic acids 19(T)

630 Index

central-atom names 543(T) 'sexi-' 539 138, 149, 150 central atoms 435, 463 Si compounds 403 spiro polymers 532 chains 41 general naming 13 'spirosolane' 518 compound classes 19(T) seniority 27(T) spirostanes 516 coordination compounds 434 Si-heterochains 405 'squalene' 523 C-oxoacids 229 Si-heterocycles 403 'SR ', stereodescriptor 572 cyanides, isocyanides, and analogs Si-oxoacids 253 SRU, see structural repeating unit (IUPAC) 321(T) seniority 23(T) standard valences 543(T), 593 definition 8 Si-containing fused polycycles 95, 114 'stanna-' 543(T) element names 543(T) sign '' 27(T), 63, 405 esters 267 , definition 2 'stannan(o)-', bridge name 127(T) functional parents 41 >, definition 2 stannathianes 65 helix unit 560 ~, definition 2 'stannyl-' 64, 405 heteroatom syllables 543(T) Si-heteromonocycles 82ff. 'stannylene-' 405 hydrazides 313, 317 'sila-' 543(T) 'stannylidyne-' 405 hydrazones 326, 333 'silacyclohexane' 78(T) 'starch' 507 hydrocarbon chains 426 '' 27(T), 63, 405 'stearamide' 301 index names 48 'silane, monoprotonated' 170 'stearic acid'/ 'stearoyl-' 204 in the δ convention 597 'silane ion(1–)' 188 stereodescriptors 571 ligands 'silan(o)-', bridge name 127(T) 'α-d' or 'α-l' 498 in coordination compounds 582 'silanthrene' 91(T), 114 'α' or 'β' in organometallic compounds 582 silathianes 65 CA stereodescriptors until 1999 573ff. in stereoisomers 560, 561, 566 silazanes 65 citation in names 572 molecular-skeleton parents 41 'silicate' 190, 253, 271 meso ring structures 573 monosaccharide residues 505 silicic acids steroids 516, 571 monosaccharides 496 anhydrides 259 terpenes 520, 571 monosulfones, monosulfoxides, monosul- formal acid halides 292 'β-d' or 'β-l' 498 fides, and analogs with replace- formal amides 308 '∆' or 'Λ', determination 583 ment names 420 formal hydrazides 318 'ξ' multivalent component in polymers 531 salts 253 steroids 516, 571 naming of the nonsenior central atom 465 seniority 23(T) terpenes 520, 571 N-heterochains with replacement names Si-oxoacids 253 '(±)' 572 375 'silicide' 188 amino acids 210, 490 nonstandard valences 597 silicon compounds, see Si compounds 'anti ' or 'syn' nucleoside or nucleotide residues 512f. silicon-containing oxoacids, see Si-oxoacids CA stereodescriptors until 1999 573ff. O-heterochains with replacement names 'siliconium' 170 citation in names 572 411 siloxanes 65 von Baeyer bridged polycycles 120, 573 'onia-' syllables 543(T) polymers 531 'aR ' or 'aS ' 561 organometallic compounds 434 'silyl-' 64, 405 carbohydrates 494ff., 498 oximes 326, 333 'silylene-' 405 CA stereodescriptors until 1999 573ff. P- and As-heterochains with replacement '-' 405 'cisoid ' or 'transoid ' 573 names 388 '(silyloxy)-' 406 'cis' or 'trans' P- and As-oxoacids 22(T), 243 'N-silylsilanamine' 27(T) by IUPAC 573 parent component 89(T), 91(T) skew line 583 CA stereodescriptors until 1999 573ff. parent substituents 41, 153 Sn compounds 403, 458 citation in names 572 peroxides 411 seniority 27(T) monocycles and ring assemblies 573 peroxy acids with suffix 19(T) stereodescriptors 582, 585 citation polyoxides 411 Sn-heterochains 405 in index names 572 replacement names 61 Sn-heterocycles 403 in names (general) 572 ring assemblies 141 'sodio-' 436 in names of organometallic and coordi- rings 42ff. software nation compounds 582 S-, Se-, and Te-heterochains with replace- nomenclature 1, 537 'C ' or 'A', determination 583 ment names 420 POLCYC for von Baeyer bridged-poly- cyclitols 509 Sb- and Bi-heterochains with replacement cycle names 117 'd ', obsolete 572 names 394 'solanidane' 488, 518 definition 8 set of locants 49 solvates, lit. 536 'd' or 'l' Si-, Ge-, Sn-, and Pb-heterochains with 'sorbic acid'/ 'sorboyl-' 206 amino acids 210, 490, 571 replacement names 407 'sorbose' 495 carbohydrates 494, 571 Si, Ge, Sn, and Pb compounds 403 specialist names (see also specialist nomen- cyclitols 509 stereoparents 41 clatures), definition 8 peptides 571 sulfonic acids and analogs 19(T) specialist nomenclatures (see also specialist 'E '/ 'Z ' 572 'sulfoximine' and 'sulfilimine' 376 names) 'endo' or 'exo' ' ' and 'sulfur triimide' 377 collection 487 CA stereodescriptors until 1999 573ff. 'unexpressed amides' 297, 313 general naming 13 citation in names 572 senior ring structure specification of the configuration559 von Baeyer bridged polycycles 120, 573 C compounds 426 'spiro-' 133, 135, 541 'E ' or 'Z ' definition 8 spiro atom, locant pair 136 assignment of configuration 561 determination of molecular-skeleton 'spirobi-' 136 CA stereodescriptors until 1999 574ff. parents 42ff. spiropolycycles 133 citation in names 572 '(sep)', ligand-name abbreviation 482(T) 'added' indicated H atom 551 hydrazones 330, 341 'septi-' 539 indicated H atom 548 hydrocarbon chains 55 sequence rules 564, 582 with carbomonocycle or heteromonocycle imines 367 '(ser)', ligand-name abbreviation 482(T) components 133 oximes 329, 340 '(serinato)', ligand name for abbreviation with fused-polycycle components or von 'l ', obsolete 572 482(T) Baeyer bridged-polycycle compo- locants 572 'serine'/ 'seryl-' 211, 491 nents 135 'M ' or 'P ' sesquiterpenes 522 with identical components 136 assignment of configuration 560 sesterpenes 523 spiropolycycle substituents, prefixes 134, citation in names 571

631 Index

stereodescriptors (cont.) 'stibo-' 393 'sulfate' 190, 237, 271 'MP ' or 'PM ' 572 'stibonio-' 182 'sulfato-' 240, 276 '(+)' or '(–)' 572 'stibonium' 170 '[sulfato(2–)]', ligand name 445(T) 'partial ' 'stibono-' 393 '-sulfenamide' 298(T) CA stereodescriptors until 1999 574ff. 'stiborane' 392 sulfene 343 'pR ' or 'pS ' 561 'stiboso-' 393 'sulfene' 326, 333 'r', 'c', and 't ' 573 'stibylene', ligand name 443(T) '-sulfenic acid' 21(T), 223 'R*' or 'S*' 'stibylene-' 392 sulfenic acid esters by IUPAC 572 'stibylidyne-' 392 formal di- or trichalcogenides 418 CA stereodescriptors until 1999 573ff. '(stien)', ligand-name abbreviation 482(T) formal thioperoxides 410 'rac' 573 'stigmastane' 516 sulfenic acids 223 'rel ' 'stilbene' 69 formal hydrazides 314 citation in names 572 '(stilbenediamine)', incorrect ligand name seniority 20(T) meso compounds 572 for abbreviation 482(T) 'sulfeno-' 21(T), 153, 223, 355 'R ' or 'S ' '(stilbenediaminetetraacetato)', ligand name '-sulfenoperoxoic acid' 19(T), 226 assignment of configuration 560 for abbreviation 482(T) sulfenoperoxoic acids and analogs 226 CA stereodescriptors until 1999 573ff. STN® network 1 sulfenothioic acids and analogs 224 citation in names 571 Stock number, see oxidation number '-sulfenyl', acid halide suffix 286(T) stereogenic central atom, determina- stoichiometric proportions of coordination 'sulfide' 36 tion 583 ions 434 anion 237 'RS ' or 'SR ' 572 'streptamine' 509 nonstandard valences 594 'stereoisomer' 574, 591 structural repeating unit 531 pseudoketones 339 steroids 516 structure descriptor in coordination names S-, Se-, and Te-heterocycles 416 terpenes 520 467 sulfides stereogenic axis 'strychnidine' 488 functional-class nomenclature 38 assignment of configuration 560f. 'styphnate' 193 sulfides and analogs 27(T), 419f. definition 559 'styphnic acid' 351 'sulfido-' 36 sequence rules 567 'styrene' 69 nonstandard valences 594 stereodescriptors 'aR ' or 'aS ' 561 'styryl-' 69 pseudoketones 339 stereogenic center 'suberic acid'/ 'suberoyl-' 204 S-, Se-, and Te-heterocycles 416 assignment of configuration 560 substituents 'sulfilimine' 26(T),376 , 421 definition 559 composite 'sulfimide' 26(T), 378, 422 sequence rules 566 alphabetical order of prefixes 53 sulfimides 339 stereogenic double bond multiplying affixes 539 '-sulfinamide' 298(T) assignment of configuration 561 compulsory prefixes 18 (T) sulfine 343 definition 560 definition 8 'sulfine' 326, 333 sequence rules 568 general naming 13 '-sulfinic acid' 21(T), 223 stereogenic units 559 simple, multiplying affixes 539, 540(T) sulfinic acids 223 'stereoisomer' 572, 574, 591 substituting groups, definition 8 seniority 20(T) stereoisomers 557 substitutive names sulfinimidic acids and analogs 224f. stereomodel 558 acyclic ethers 412 'sulfinimidoyl-' 376 stereoparent names acyclic monosulfones, monosulfoxides, 'sulfino-' 21(T), 153, 223 alkaloids 487, 489 monosulfides, and analogs 420 sulfinohydrazonic acids and analogs 224f. amino acids 210, 490 definition 8 sulfinohydroximic acids 225 bile pigments 530 substitutive nomenclature (see also substitu- '-sulfinoperoxoic acid' 19(T), 226 carbohydrates 494 tive names) 29 sulfinoperoxoic acids and analogs 226 carotenoids 524 general naming 14 '-sulfinothioamide' and analogs 298(T) cyclitols 509 subtractive names, definition 8 sulfinothioic acids and analogs 224 definition 8 subtractive nomenclature (see also subtrac- '-sulfinothioyl' and analogs, acid halide suf- general naming 14 tive names) 37 fixes 286(T) location of drawings of formulas 487 subtractive prefixes, alphabetical order 53 'sulfinyl-', multivalent substituent 34(T) nucleosides 510 'succinamic acid' 214 '-sulfinyl-' 18(T) nucleotides 511 'succinamide' 301 '(sulfinylamino)-' 378 porphyrins 529 'succinanilic acid' 214 '-sulfinyl' and analogs, acid halide suffixes seniority 41 'succinic acid'/ 'succinyl-' 204 286(T) stereodescriptors 571 'succinimide'/ 'succinimido-' 296 '-sulfinyl-' and analogs steroids 516 'succinimidoyl-' 217 acid halides 288 terpenes 520 'sucrose' 505 amides 303, 306 vitamins 526 suffixes esters 275, 276, 278 stereoparents (see also stereoparent names), compound classes 19ff.(T) monosulfoxides and analogs 421 definition 6 conjunctive nomenclature 31 S-, Se-, and Te-oxoacids 240 steroids 516 definition 8 sulfinic acids and analogs 225 stereodescriptors 571 for identical structure units, multiplicative 'sulfite' 190, 238, 271 'stiba-' 543(T) nomenclature 32 '[sulfito(2–)]', ligand name 445(T) 'stibane' 63, 392 general naming 13 'sulfo', ligand name 442(T) 'stibinane' 78(T) locants 49 'sulfo-' 20(T), 153, 223, 278 '' 26(T), 63, 392 multiplying affixes 539 '(sulfoamino)-' 239, 240, 306 'stibine imide' 26(T), 367, 393 substitutive nomenclature 29 'sulfolane' 339, 422 'stibine ion(1–)' 188 'sulfamate' 190, 239, 271 '-sulfonamide' 298(T) 'stibine oxide' 26(T), 393 'sulfamic acid' 21(T), 239 '-sulfonamido-' 303 'stibine sulfide' 26(T) 'sulfamide' 306 sulfones 339 'stibine sulfide' and analogs 393 'sulfamoyl' 239 functional-class nomenclature 38 'stibinic acid' 395 'sulfamoyl-' 240 general naming 13 'stibinico-' 393 'sulfamoyl chloride' 290 sulfones and analogs 27(T), 419f. 'stibinimine' 393 '(sulfamoyloxy)-' 277 '-sulfonic acid' 20(T), 223 'stibinin' 78(T) 'sulfane' 63, 223, 416 sulfonic acids 223 'stibino', ligand name 443(T) 'sulfanilic acid' 223, 492 seniority 20(T) 'stibino-' 64, 392 '-' 347 sulfonic acids and analogs, salts 227

632 Index

'-sulfonimidamide' 298(T) sultones 23(T), 268 pseudoketones 339 '-sulfonimidic acid' 20(T), 225 'superoxido', ligand name 443(T) '2H-tellurin' 74 sulfonimidic acids and analogs 224f. sydnone imines 196 '-tellurinamide' 298(T) 'sulfonimidoyl-' 376 sydnones 196 '-tellurinic acid' 223 '-sulfonimidoyl' and analogs, acid halide 'syn' tellurinic acids 223 suffixes 286(T) CA stereodescriptors until 1999 573ff. 'tellurino-' 223 '-sulfonimidoyl-' and analogs citation in names 572 '-tellurinyl', acid halide suffix 286(T) acid halides 288 von Baeyer bridged polycycles 120, 573 '-tellurinyl-' 18(T), 225, 288, 421 amides 303, 306 systematic names, definition 8 tellurium compounds, see Te compounds esters 275, 276, 278 tellurium-containing oxoacids, see Te-oxo- S-, Se-, and Te-oxoacids 240 acids sulfonic acids and analogs 225 't ' 599(T) 'telluro-', multivalent substituent 34(T) 'sulfonio-' 182 stereodescriptor 573 '-telluro', radical name 164 'sulfonium' 170 ' T ' 599(T) '-telluro-' 18(T), 225, 288, 421 '-sulfonohydrazide' 314 '(tacn)', ligand-name abbreviation 472(T), telluroanhydrides, see anhydrotellurides '-sulfonohydrazonamide' 298(T) 482(T) '-tellurol' 25(T), 347 '-sulfonohydrazonic acid' 20(T), 225 'tagatose' 495 'tellurolo-' 91(T), 102 sulfonohydrazonic acids and analogs 224f. 'talo-' 495 '-telluronamide' 298(T) '-sulfonohydrazonimidic acid' 20(T), 225 'talose' 495 'tellurone' 333 '-sulfonohydrazonoyl' and analogs, acid '(tap)', ligand-name abbreviation 482(T) '-telluronic acid' 21(T), 223 halide suffixes 286(T) '(tart)', ligand-name abbreviation 439, 482(T) telluronic acids 223 '-sulfonohydrazonoyl-' and analogs 'tartaramide' 301 seniority 20(T) acid halides 288 'tartaric acid'/ 'tartaroyl-' 209 'telluronio-' 182 amides 303, 306 'tartrate' 192 'telluronium' 170 esters 275, 276, 278 '(tartrato)', ligand name for abbreviation 'tellurono-' 21(T), 223 S-, Se-, and Te-oxoacids 240 439, 482(T) '-telluronyl', acid halide suffix 286(T) sulfonic acids and analogs 225 'tartronic acid'/ 'tartronoyl-' 209 '-telluronyl-' 18(T), 225, 288, 421 sulfonohydroximic acids 225 'taurine' 223, 492 'tellurophene' 73, 91(T) '-sulfonoperoxoic acid' 19(T), 226 'tauryl-' 226 'tellurophene-2-yl-' 76 sulfonoperoxoic acids and analogs 226 tautomers 'telluroxo-' '-sulfonothioamide' and analogs 298(T) carbohydrazonic and carboximidic acids acid halides 288 '-sulfonothioic acid' 20(T), 224 216 aldehydes 25(T), 327 sulfonothioic acids and analogs 224 carbothioic acids and chalcogen analogs amides 303, 305 '-sulfonothioyl' and analogs, acid halide suf- 215 carboxylic acids 217 fixes 286(T) C-oxoacids with infixes in the name 229, C-oxoacids 233 '-sulfonothioyl-' and analogs 230 esters 275, 276, 278 acid halides 288 lit. (CA) 536 ketones 25(T), 334ff. amides 303, 306 P- and As-oxoacids with infixes in the prefix 156f. esters 275, 276, 278 name 245 radicals 163 S-, Se-, and Te-oxoacids 240 sulfonohydrazonic and sulfonimidic acids '(telluroxomethyl)-' 25(T) sulfonic acids and analogs 225 and analogs 224, 225 'telluryl' 'sulfonyl-', multivalent substituent 34(T) sulfonothioic acids and analogs 224 ligand name 438, 442(T) '-sulfonyl-' 18(T) 'taxane' 522 radical name 163 '(sulfonylamino)-' 378 'TCNE' 322 'telluryl-' 25(T), 153, 347, 350 '-sulfonyl' and analogs, acid halide suffixes '(tcne)', ligand-name abbreviation 482(T) telomers 534 286(T) 'TCNQ' 323 'ter-' 141, 539 '-sulfonyl-' and analogs '(tcnq)', ligand-name abbreviation 482(T) 'terephthalamide' 301 acid halides 288 'Td', nucleoside abbreviation 511 'terephthalic acid'/ 'terephthaloyl-' 205 amides 303, 306 '(tdt)', ligand-name abbreviation 482(T) terpenes 520 esters 275, 276, 278 Te compounds 415 carbomonocycles 67 monosulfones and analogs 421 seniority 27(T) carbopolycycles 117 S-, Se-, and Te-oxoacids 240 Te-heterochains 416ff. stereodescriptors 571 sulfonic acids and analogs 225 Te-heterocycles 415 'terpinolene' 521 '(sulfooxy)-' 240, 276 Te-oxoacids 237 '(terpy)', ligand-name abbreviation 482(T) sulfoxides 339 salts 237 '(terpyridine)', ligand name for abbreviation functional-class nomenclature 38 seniority 21(T) 482(T) general naming 13 '(tea)', ligand-name abbreviation 482(T) 'tert-' 541 sulfoxides and analogs 27(T), 419f. 'tellane' 63, 223 tertiary amines 360 'sulfoximine' 26(T), 376, 421 'tellanyl-' 347 '(2,3,2-tet)', ligand-name abbreviation 482(T) sulfoximines 339 '-tellone' 25(T), 333ff., 416 '(3,3,3-tet)', ligand-name abbreviation 482(T) 'sulfoxonium' 170 'tellura-' 543(T) 'tetra-' 540(T) 'sulfoxylate' 238 '-tellural' 25(T), 327 '(1,5,9,13-tetraazatridecane)', ligand name 'sulfoxylic acid' 238 'tellurate' 238 for abbreviation 482(T) sulfoxylic acids, seniority 21(T) 'tellurazole' 79 '(1,4,8,11-tetraazaundecane)', ligand name 'sulfuramidic acid' 239 'tellurazolidine' 79 for abbreviation 482(T) sulfur compounds, see S compounds '-tellurenamide' 298(T) 'tetraconta-' 540(T) sulfur-containing oxoacids, see S-oxoacids '-tellurenic acid' 223 'tetracosa-' 540(T) 'sulfur diimide' 19(T), 26(T), 377, 422 tellurenic acids 223 'tetracta-' 540(T) 'sulfuric acid' 237 'tellureno-' 223 'tetracyanoethylene' 322 sulfuric acids, seniority 21(T) '-tellurenyl', acid halide suffix 286(T) '(tetracyanoethylene)', ligand name for 'sulfurous acid' 238 'telluric acid' 238 abbreviation 482(T) sulfurous acids, seniority 21(T) telluric acids, seniority 21(T) 'tetracyanoquinodimethane' 323 'sulfur triimide' 26(T), 377, 422 'telluridato', ligand name 444 '(tetracyanoquinodimethane)', ligand name 'sulfuryl', acid halides 290 'telluride' 36 for abbreviation 482(T) 'sulfuryl hydrazide' 317 nonstandard valences 594 'tetradeca-' 540(T) '-sultam' 295 pseudoketones 339 '(tetraethylenepentamine)', ligand name for sultams 23(T), 295 'tellurido-' 36 abbreviation 482(T) '-sultone' 268 nonstandard valences 594 'tetrahedro' 467

633 Index

'(tetrahydrofuran)', ligand name for abbre- '(thiocarboxy)-' 20(T), 215 'thiothionyl', acid halides 290 viation 482(T) thiocarboxylic acids and analogs, see carbo- 'thiouracil' 309 '(tetrahydrothiophene)', ligand name for thioic acids and analogs 'thiouram disulfide' 304, 418 abbreviation 482(T) 'thiochromane' and chalcogen analogs 87 'thiouram monosulfide' 304, 418 'tetrakis-' 539 'thiochromene' and chalcogen analogs 92(T) 'thiourea' and analogs 230, 304 'tetralia-' 540(T) thiocyanates and analogs, functional-class '(thiox)', ligand-name abbreviation 482(T) tetraligant atoms 561, 584 names 321(T) '(thioxane)', ligand name for abbreviation '(5,10,15,20-tetramesitylporphyrin-21,23- 'thiocyanato-' and analogs 321(T) 482(T) diido)', ligand name for abbrevia- acid halides 288 '9H-thioxanthene', exception of numbering tion 484(T) affixes in S-, Se-, and N-oxoacid names 92(T) 'tetraoxide' 410 238 'thioxo-' '-tetraoxy-' 410 amides 305 acid halides 288 'tetraphenylene' 90(T) C-oxoacids 233 aldehydes 24(T), 327 tetrapyrroles 529 esters 276 amides 303, 305 '(5,10,15,20-tetra-p-tolylporphyrin-21,23- P- and As-oxoacids 248 carboxylic acids 217 diido)', ligand name for abbrevia- S-, Se-, and Te-oxoacids 240 C-oxoacids 233 tion 484(T) '' 21(T) esters 275, 276, 278 'tetrazane-1,4-diyl-', multivalent substituent 'thiocyanic acid' and analogs 230, 287 ketones 25(T), 334ff. 34(T) thioesters, formal oxides 271, 273 prefix 156f. '(tetren)', ligand-name abbreviation 482(T) thioethers, of peptides 492 radicals 163 '(tfa)', ligand-name abbreviation 482(T) 'thioformic acid' 231 'thioxo' and analogs, ligand names 442(T) 'thalidomide' 309 '(thioformyl)-' and analogs 157, 233, 327 '(thioxomethyl)-' 24(T) 'thebaine' 489 'thiohydroperoxide' 25(T), 355 '(thioxomethyl)-' and analogs 233, 327 'thebenidine' 94(T) thiohydroperoxides 355 '-thioyl' and analogs, acid halide suffixes 'thenoic acid'/ 'thenoyl-' 205 seniority 25(T) 286(T) '(thenoyltrifluoroacetonato)', ligand name thiohydroxylamine and analogs '-thioyl-' and analogs, acyl prefix 217 for abbreviation 484(T) alcohols 350 '(thr)', ligand-name abbreviation 482(T) 'thenyl-' 75 amines 363 'threo-' 496 'thevinone' 489 N-heterochains 375 '(threoninato)', ligand name for abbreviation '(thf)', ligand-name abbreviation 482(T) seniority 26(T) 482(T) 'thia-' 541, 543(T) 'thiohydroxylamin-S-sulfonic acid' 239 'threonine'/ 'threonyl-' 212, 491 '-thial' 24(T), 327 'thiohypochlorous acid' 287, 289, 291 'threose' 495 'thiamine' 526 '-thioic acid' 20(T), 214 '(tht)', ligand-name abbreviation 482(T) 'thianthrene' 91(T) '6-thioinosine' 511 'thujane' 520 'thiazole' 79 thioketals 419 'thujene' 521 '(thiazole)', ligand name for abbreviation thioketones and analogs 333 '(thy)', ligand-name abbreviation 484(T) 484(T) seniority 25(T) 'thymidine' 511 'thiazolidine' 79 '-thiol' 25(T), 347 'thymidylic acid' 511 'thieno-' 91(T), 102 '-thiolate' and analogs 191 'thymidylyl-' 512 'thienyl-' 75, 91(T), 150 '-thiolato' and analogs, ligand names 444 'thymine' 309, 510 '-thien-x-yl-' 112, 150 thiols and analogs 347 '(thymine)', ligand name for abbreviation 'thio-' 'Class-I' 268f. 484(T) monosaccharides 503 'Class-II' 268 'thymol' 347 multivalent substituent 34(T) common 268f. 'thymyl-' 70 nucleosides 510, 512 exotic 268 'thyronine' 212, 492 '-thio', radical name 164 seniority 25(T) 'thyroxine' 214, 492 'thioacetaldehyde' 328 'thiomorpholine' 75 tin compounds, see Sn compounds thioacetals 419 '-thionato' and analogs, ligand names 444 '(tmen)', ligand-name abbreviation 484(T) '-thioacetamide' 302 '-thione' 25(T), 333ff. '(tmp)', ligand-name abbreviation 484(T) 'thioacetic acid' 215 '(thionitroso)-' 240, 276, 306 '(tn)', ligand-name abbreviation 484(T) '(thioacetyl)-' 217 'thionitrosyl', acid halides 290 'tocopherols' 528 thioaldehydes and analogs 325 'thionyl', acid halides 290 '(m-Tol)', ligand-name abbreviation 484(T) seniority 24(T) 'thionyl imide' 26(T), 378, 422 '(o-Tol)', ligand-name abbreviation 484(T) '-thioamide' and analogs 298(T) thionyl imides 339 '(p-Tol)', ligand-name abbreviation 484(T) 'thio-' and analogs, affixes in names thioorthocarboxylic acid ester 419 'toluene' 69 of boronic and borinic acids 255 'thioorthoformate' 421 'toluenedisulfonic acid' 227 of S-, Se-, and N-oxoacids 238 'thiooxime' 329, 340 'toluenesulfonamide' 302 of silicic acids 253 'thioperoxide' 410 'toluenesulfonic acid' 223 '-thio-' and analogs '-(thioperoxo)-' and analogs, infixes in names 'toluic acid'/ 'toluoyl-' 205 acid halides 288 of carboxylic acids 218 'toluidine' 360 amides 303 of C-oxoacids 230 'toluidino-' 360 esters 274ff. of P- and As-oxoacids 245 '(m-tolyl)', ligand name for abbreviation 484(T) monosulfides and analogs 421 of sulfonic acids and analogs 226 '(o-tolyl), ligand name for abbreviation 484(T) prefixes 18(T) '-(thioperoxoic) acid' 218 '(p-tolyl)', ligand name for abbreviation 484(T) S-, Se-, Te-, and N-oxoacids' 240 'thiophene' 73, 91(T) 'tolyl-' 69 sulfenic acids and analogs 225 'thiophenol' 349 torsion angle 560, 561 '-thio-' and analogs, infixes in names '2H-thiopyran' 74, 92(T) 'tosyl-' 226, 287, 421 of carboxylic acids 214 'thiopyrylium' 179 'tosylate' 226 of C-oxoacids 229 'thiosalicylic acid' 209, 351 '(Tp')', ligand-name abbreviation 484(T) of P- and As-oxoacids 245 '(thioseleneno)-' 153, 224 '(Tp)', ligand-name abbreviation 484(T) of sulfonic acids and analogs 224 thiosilicic acids, seniority 23(T) '(Tp*)', ligand-name abbreviation 484(T) Me 'thioanhydride' and analogs 258, 261 '(thiosulfeno)', ligand name 442(T) '(Tp 2)', ligand-name abbreviation 484(T) thioanhydrides, see anhydrosulfides '(thiosulfeno)-' 153, 224 '(tpp)', ligand-name abbreviation 484(T) 'thiobenzoic acid' 215 '(thiosulfino)-' 224 'trans' '(thiobenzoyl)-' 217 '(thiosulfo)-' 20(T), 224 by IUPAC 573 '(thiocarbamoyl)-' 233 thiosulfonic acids, see sulfonothioic acids CA stereodescriptors until 1999 573ff. '(thiocarbamoyl)-' and analogs 298(T) and analogs citation in names 572 '(thiocarbonyl)-' and analogs 157, 217, 233, 337 'thiosulfuryl', acid halides 290 monocycles and ring assemblies 573

634 Index transformation conventions, CIP system cross-references to systematic names 487 'vanillin' 331 561ff., 584 definition 8 'vasopressin' 493 trans maximum difference of priority num- trivial syllable 'alka-' 55 'veatchane' 489 bers 471, 582 'tropic acid'/ 'tropoyl-' 209 'veratraman' 518 'trans' not senior to 'cis', CIP system 566 'tropine' 487 'veratric acid'/ 'veratroyl-' 209 'transoid ', stereodescriptor 573 '(trp)', ligand-name abbreviation 484(T) 'veratrole' 414 '(tren)', ligand-name abbreviation 484(T) '(tryptophanato)', ligand name for abbrevia- 'vincaleukoblastin' 489 'tri-' 540(T) tion 484(T) 'vinyl-' 56 'triaconta-' 540(T) 'tryptophane'/ 'tryptophyl-' 212, 491 '' 348 '(1,2,3-triaminopropane)', ligand name for '(tsalen)', ligand-name abbreviation 484(T) 'vinylidene-' 58 abbreviation 482(T) '(ttfa)', ligand-name abbreviation 484(T) 'vinylium' 176 'triangulo' 467 '(ttha)', ligand-name abbreviation 484(T) 'violanthrene' 87 'triarsine' 26(T) '(ttp)', ligand-name abbreviation 484(T) 'violaxanthin' 525 'triarsorane' 26(T) '(tu)', ligand-name abbreviation 484(T) 'vitamin A1' 522, 526 '(1,4,7-triazacyclononane)', ligand name for '(tyr)', ligand-name abbreviation 484(T) 'vitamin A2' 522, 526 abbreviation 472(T) '(tyrosinato)', ligand name for abbreviation 'vitamin B' 528 '' 26(T) 484(T) 'vitamin B1' 526 'triaz-1-ene' 26(T) 'tyrosine'/ 'tyrosyl-' 212, 491 'vitamin B2' 526 'tribenzamide' 301 '(tz)', ligand-name abbreviation 484(T) 'vitamin B3' 526 'tribismuthine' 26(T) 'vitamin B4' 364, 510, 526 'trichothecane' 522 'vitamin B5' 214, 492, 526 'tricosa-' 540(T) ' U ', nucleoside abbreviation 511 'vitamin B6' 351, 526 'tricta-' 540(T) '-uida-' 193 'vitamin B7' 526 'tricyclo-' 117 '-uide' 193 'vitamin B9' 493 'trideca-' 540(T) '-ulosaric acid' 497 'vitamin B12' 527 '(trien)', ligand-name abbreviation 439, ulosaric acids 497 'vitamin Bc' 493 484(T), 588 '-ulose' 496 'vitamin C' 495, 527 '(triethanolaminato)', ligand name for abbre- uloses 496 'vitamin D1' 527 viation 482(T) '-ulosonic acid' 497 'vitamin D2' 527 'triethylamine' 361 ulosonic acids 497 'vitamin D3' 527 '(triethylenetetramine)', ligand name for '-ulosuronic acid' 497 'vitamin D4' 527 abbreviation 439, 484(T), 588 ulosuronic acids 497 'vitamin D5' 528 '(triethylenetetraminehexaacetato)', ligand 'undeca-' 540(T) 'vitamin E' 528 name for abbreviation 484(T) 'undeci-' 539 'vitamin G' 526 'triflate' 226, 406 'unexpressed amides' 'vitamin H' 526 '(trifluoroacetylacetonato)', ligand name for amides 297 'vitamin K1 528 abbreviation 478(T) general naming 25(T) 'vitamin K2' 528 'trilia-' 540(T) hydrazides 313 'vitamin K3' 528 'trimethylene-' 56 ketones 337 'vitamin PP' 528 '(trimethylenediamine)', ligand name for N-heterocycles 372 vitamins 526 abbreviation 484(T) unsaturated bridge termini, indicated H von Baeyer bridged carbopolycycles 117 'trimethylsilyl triflate' 406 atom 549 von Baeyer bridged heteropolycycles 118 'trimol. dianhydride' 259 unsaturations von Baeyer bridged polycycles 117 'trinaphthylene' 90(T) general naming 13 locants of unsaturations 49, 119 '1H-trindene' 89(T) hydrocarbon chains 55 von Baeyer bridged-polycycle substituents, 'trinorbornane' 521 monosaccharides 503 prefixes 120, 149, 150 'trinorcarane' 520 locants 49, 51 von Baeyer names, see von Baeyer bridged 'trioxide' 27(T), 258, 260, 410 in von Baeyer bridged polycycles 49, 119 polycycles '-trioxy-' 410 multiplying affixes 539 vowels 9 'triphenodioxazine' 94(T) polymers 531 'triphenodithiazine' 94(T) steroids 517 'triphenylcarbinol' 349 subtractive nomenclature 37 ' X ', nucleoside abbreviation 511 'triphenylene' 89(T) transformation convention in the CIP '9H-xanthene', exception of numbering '(triphos)', ligand-name abbreviation 484(T) system 562, 584 92(T), 112 'triphosphine' 26(T) '(ura)', ligand-name abbreviation 484(T) 'xanthic acid' 271, 273 'triphosphorane' 26(T) 'uracil' 309, 510 'xanthine' 309, 510 '(tris)', ligand-name abbreviation 484(T) '(uracil)', ligand name for abbreviation xanthophylls 524 'tris-' 539 484(T) 'xanthosine' 511 trisaccharides 505 'urea' 230, 304 'xanthylic acid' 511 '[tris(2-aminoethyl)amine]', ligand name for 'ureido-' 305 'xanthylium' 179 abbreviation 484(T) 'urethane' 271, 273 'xanthylyl-' 512 'triselenide' 27(T), 258, 260, 417 'ureylene-' 305 xi descriptor, see stereodescriptors 'ξ' 'triseleno-', multivalent substituent 34(T) 'uric acid' 309 'xylene' 69 '' 27(T) 'uridine' 511 'xylenyl-' 70 'tristibine' 26(T) 'uridylic acid' 511 'xylidine' 364 'trisulfide' 27(T), 258, 260, 417 'uridylyl-' 512 'xylo-' 494 'trisulfone' and analogs 27(T), 416 '-uronic acid' 497 'xylose' 494 'trisulfoxide' and analogs 416 '-uronium' (+ E+) 174 'xylyl-' 70 'tritelluride' 27(T), 258, 260, 417 uronium ions 173 triterpenes 523 'ursane' 523 '(1,4,7-trithiacyclononane)', ligand name for '-yl', radical name 19(T), 161 abbreviation 472(T) '-yl-' 'trithio-', multivalent substituent 34(T) '(val)', ligand-name abbreviation 484(T) bridged fused-polycycle substituents 128, '-trithio-' and analogs, prefixes 417 'valeric acid'/ 'valeryl-' 204 149, 150 'trityl-' 69 '(valinato)', ligand name for abbreviation carbomonocycle substituents 67, 148 'trityl alcohol' 349 484(T) cation substituents 182 'tritylium' 175 'valine'/ 'valyl-' 212, 491 fused-polycycle substituents 87, 112, 115, trivial names 'vanillic acid'/ 'vanilloyl-' 209 149, 150

635 Index

'-yl-' (cont.) heterochain substituents 62ff., 147 heteromonocycle substituents 75, 77, 82, 84, 150 hydrocarbon-chain substituents 56, 146 mononuclear substituents 145 ring-assembly substituents 142, 152 spiropolycycle substituents 134, 138, 149, 150 von Baeyer bridged-polycycle substituents 120, 149, 150 '-ylene-' carbomonocycle substituents 68, 148 hydrocarbon-chain substituents 56 mononuclear substituents 145 '-ylide', zwitterion 195, 196 '-ylidene', radical name 161 '-ylidene-' bridged fused-polycycle substituents 128, 149, 150 carbomonocycle substituents 68, 148 cation substituents 182 fused-polycycle substituents 87, 112, 115, 149, 150 heterochain substituents 62ff., 147 heteromonocycle substituents 75, 77, 82, 84, 150 hydrocarbon-chain substituents 56, 146 ring-assembly substituents 142, 152 spiropolycycle substituents 134, 138, 149, 150 von Baeyer bridged-polycycle substituents 120, 149, 150 '-ylidyne', radical name 161 '-ylidyne-' cation substituents 182 heterochain substituents 62ff., 147 hydrocarbon-chain substituents 56, 146 mononuclear substituents 145 '-ylium' minus H– 175, 176 minus OH– 176f. '-yliumide', zwitterion 195 '-yliumuide', zwitterion 195 '-yliumyl', radical cation 200 '-yliumyl-', cation (prefix) 182 '-yne' carbomonocycles 67, 82 heterochains 61ff. hydrocarbon chains 55 monosaccharides 503 polymers 531 spiropolycycles 134 steroids 517 subtractive nomenclature 37 von Baeyer bridged polycycles 118 '-ynyl-' carbomonocycle substituents 67, 148 hydrocarbon-chain substituents 56, 146 '-ynylidene-' carbomonocycle substituents 68, 148 hydrocarbon-chain substituents 56, 146 '-ynylidyne-', hydrocarbon-chain substitu- ents 56, 146 'yohimban' 489

'Z ' assignment of configuration 561 CA stereodescriptors until 1999 574ff. citation in names 572 hydrazones 330, 341 hydrocarbon chains 55 imines 367 oximes 329, 340 zwitterions 195

636