Organic nomenclature in Chinese

The Chinese Chemical Society[lower-alpha 1] (CCS; simplified Chinese: 中国化学会; traditional Chinese: 中國化學會) lays out a set of rules based on those given by the International Union of Pure and Applied Chemistry (IUPAC) for the purpose of systematic organic nomenclature in Chinese. The chemical names derived from these rules are meant to correspond with the English IUPAC name in a manner that is close to one-to-one, while being adapted to and taking advantage of the logographic nature of the Chinese written language. A standard set of characters invented during the 20th century (vide infra), along with characters for the chemical elements and characters corresponding to standard chemical prefixes and suffixes, are used for this purpose.

Derivation of Chinese characters

The majority of the Chinese characters used for this purpose are phonosemantic compounds, with part of the character giving a general semantic category and the other part providing a pronunciation, usually based on the international (European) pronunciation. There are four common radicals (the part of the character that gives the semantic category) for these characters:

  • 火 (huǒ, fire) e.g.: 烷 (wán, alkane), common for hydrocarbons
  • 酉 (yǒu, ritual wine vessel) e.g.: 酮 (tóng, ketone), common for oxygenated functionalities
  • 艸 (cǎo, grass) e.g. 苯 (běn, benzene, phenyl), common for aromatic compounds and terpenes
  • 肉 (ròu, meat, flesh) e.g. 腙 (zōng, hydrazone), common for nitrogen-containing functionalities

Additionally, the mouth radical (口, kǒu) is affixed to characters that are used for their sound only. This occurs often in the transliteration of the names of heterocyclic compounds, (e.g., 吡啶, "bǐdìng", pyridine). These characters are also used for the transliteration of non-chemical terms from foreign languages.

Table

Below is a table, in pinyin order, of the Chinese names of major organic compounds, radicals, and functional groups. Characters given are in traditional Chinese, followed by simplified Chinese where possible. Since the characters are modern creations, the traditional Chinese characters are analogous (with traditional components in place of simplified components). The Mandarin pronunciation of each character, as said in Mainland China, is in pronunciation column. Any Taiwanese pronunciations that differ from the Mainland Chinese pronunciations are put in the notes. Other usages of characters are etymologically unrelated to the character's meaning as names for organic compounds, radicals, and functional groups unless otherwise stated. This list is not exhaustive, although many of the other characters used for this purpose can only be found in specialist dictionaries.

Chinese names of organic compounds, radicals, and functional groups
CharacterPhoneticPronunciationOther meaningsOrigin/Notes
amineān 'peace'ànè (ān in Taiwan): to putrefy (of meat)'From ammonia, 氨 ān, itself based on the European pronunciation (銨/铵 ǎn 'ammonia', with the metal radical is used for ammonium salts). Pronounced as ān in Taiwan.
azuleneào 'mysterious'ào: wild grapesEuropean pronunciation
benzene or phenylběn 'this','root'běnthe appearance of grass growingEuropean pronunciation
吡啶 pyridine 'compare' and 定 dìng 'stability'bǐdìng'slander' or 'compare'
 : bird onomatopoeia
Transliteration
吡咯 pyrrole 'compare' and 各 'each'bǐluò or :'cackle', 'cluck', 'this', or 'pickled mustard';
(luò in Taiwan):'to cough up';
lo, used as an end particle.
Transliteration. See note for 吡啶 for other usages for 吡
吡喃 pyran 'compare' and 南 nán 'south'bǐnánto transliterate '-ran'.Transliteration.
吡喃鎓 pyrylium 'compare', 南 nán 'south', and 翁 wēng 'old man':bǐnánwēngCombination of transliteration for 'pyran' and suffix for 'onium'.
benzylbiàn 'hurried'biànEuropean pronunciation
卟吩 porphin 'foretell' and 分 fēn 'divide'bǔfēn卟 as 'jī': 'divination' or 'to consider'
 :'to instruct, command'.
Transliteration. Formerly known as 㗊 léi, which depicts the porphin ring system pictographically.
alcoholxiǎng 'enjoy'chún(formerly) rich wineNot newly coined
噠嗪/哒嗪 pyridazine達/达 'arrive at' and 秦 qín 'Qin Dynasty'dāqínTransliteration.
噁唑/𫫇唑 oxazole惡/恶 è 'evil' and 坐 zuò 'sit'èzuòTransliteration.
acenaphtheneè 'hardship'èEuropean pronunciation
anthraceneēn 'favor'ēna name of a grassEuropean pronunciation.
phenanthrenefēi 'not'fēifragrant
fěi:'poor'.
European pronunciation.
酚 (also 苯酚) phenolfēn 'divide'fēn (běnfēn)European pronunciation
碸/砜 sulfone風/风 fēng 'the wind'fēngEuropean pronunciation (亞碸/亚砜 yàfēng [lit. minor sulfone], is used for sulfoxide)
呋喃 furan 'husband' and 南 nán 'south'fūnánas a variant of 趺: 'back of the foot' or 'to sit cross-legged'
喃:'chattering' or 'to mumble
Transliteration.
呋咱 furazan 'husband' and 自 'self'fūzán咱 :weTransliteration
酐 (organic or inorganic) anhydridegān 'dry'gānbitter wineFrom (simplified) 干 gān 'dry'.
glycosidegān 'sweet'gān'licoriceFrom 甘 gān 'sweet'. Formerly known as 甙 dài, composed of 弋 from 代 dài 'substitute' and 甘 gān 'sweet'.
guanidineguā 'melon'guā: 'large abdomen' or 'stoutness'European pronunciation
hydroxylaminehài '9-11 pm'hǎigāi:'the flesh where hair grows on the big toe', or 'prepare'
gǎi: 'cheek'
European pronunciation. .
sulfonyl黃/黄 huáng 'yellow'huángFrom 硫磺 liúhuáng 'sulfur'; e.g., 磺胺 huáng'àn (Taiwan huáng'ān) is sulfonamide
nitrileqīng 'blue', 'green'jīngpure meatFrom cyanogen, 氰 qíng (Taiwan qīng), itself derived from 青 qīng, blue/green/cyan, cf. Prussian blue
hydrazinejǐng 'a well'jǐng'European pronunciation
isonitrile 'stop','check'From older nomenclature carbylamine (Also known as 異腈/异腈 yìjīng [lit. different nitrile])
caranejiē 'all'kǎiEuropean pronunciation
camphanekǎn 'threshold'kǎnEuropean pronunciation
喹啉 quinolinekuí 'stride' and 林 lín 'forest'kuílín啉: lán: 'greed', 'drink a round of wine', 'finish drinking' or 'piercing noise'
lìn or làn: 'stupid'.
Transliteration.
quinonekūn 'elder brother'kūnEuropean pronunciation
phosphinelínlìnliǎn: 'lack of strength'.From 磷 lín 'phosphorus', itself from 粦 lín 'will-o'-the-wisp' (Phosphonium is 鏻 lǐn, in analogy to ammonium). Pronounced as lín in Taiwan.
ether 'bewilder'drunkFrom 迷 'confusion', from anesthetic properties of diethyl ether.
mancudemàn 'graceful'mànEuropean pronunciation. The term mancude derives from maximum number of noncumulative double bonds. For example, a 7-membered mancude ring system has three double bonds in it (e.g. azepine, oxepine, ...).
amidine 'rice'European pronunciation
咪唑 imidazole 'rice' and 坐 zuò 'sit'mǐzuò咪: : onomatopoeia for cats or used to describe the appearance of a smile.Transliteration.
嘧啶 pyrimidine 'dense' and 定 dìng 'stability'mìdìngTransliteration
naphthalenenài 'persevere'nàiEuropean pronunciation
urea尿 niào 'urine'niàoFrom 尿 niào 'urine'
薴/苧 limonene寧/宁 níng 'peaceful'níng薴: messyFrom 檸檬/柠檬 níngméng 'lemon'
哌啶 piperidine𠂢 pài and 定 dìng 'stability'pàidìngTransliteration
哌嗪 piperazine𠂢 pài and 秦 qín 'Qin Dynasty'pàiqínTransliteration
pinenepài 'assign'pàiEuropean pronunciation
picene 'equal'European pronunciation
嘌呤 purinepiào 'ticket' and 令 lìng 'make'piàolìng嘌: piāo:'passing swiftly' or 'speak'.
呤:líng: 'speak with a soft voice'
Transliteration. Pronounced as piāolíng in Taiwan..
羥/羟 hydroxylyáng 'sheep' and 巠/𢀖 jīngqiǎng'a type of sheep'.From fusion of the sounds of 氧 yǎng 'oxygen' and 氫/氢 qīng 'hydrogen'.
巰/巯 sulfhydryl巠/𢀖 jīng and 硫 liú 'sulfur'qiúFrom fusion of the sounds of 氫/氢 qīng 'hydrogen' and 硫 liú 'sulfur' (Sulfonium is 鋶/锍 liǔ, in analogy with ammonium)
aldehydequánquán'change in the flavour of wine' or 'pickled vegetables'.From 荃 quán, a type of fragrant grass, referring to the fragrance of many aldehydes.
alkyneguǎiquēguì: a surname, or 'the appearance of smoke'From 缺 quē 'deficient', referring to its unsaturation, cf. names for alkanes and alkenes. Pronounced as jué in Taiwan. .
osazoneshā 'kill'European pronunciation
噻唑 thiazolesāi 'to stop up' and 坐 zuò 'sit'sāizuòEuropean pronunciation
arsineshēn 'explain'shèn'the flesh of the back'.From 砷 shēn 'arsenic' (Arsonium is 鉮 shěn, in analogy with ammonium). Pronounced as shēn in Taiwan.
酸 (organic or inorganic) acid夋, qūnsuānsourNot newly coined
carboxyln.a.suōzuī: woollen knitwearCharacter construction is based on combination of 氧 yǎng 'oxygen' and 酸 suān 'acid', pronunciation from European pronunciation.
peptidetài 'excessively'tàiEuropean pronunciation
phthaleintài 'excessively'tàiEuropean pronunciation
carbonylyáng 'sheep' and 炭 tàn 'charcoal'tāngFrom fusion of the sounds of 氧 yǎng 'oxygen' and 碳 tàn 'carbon'. Pronounced as tàn in Taiwan.
terpenetiè 'obedient'tiēEuropean pronunciation
烴/烃 hydrocarbon巠/𢀖 jīngtīngjǐng: 'warm', 'burnt smell' or 'the appearance of burning'From fusion of the sounds of 碳 tàn 'carbon' and 氫/氢 qīng 'hydrogen'.
ketonetóng 'same'tóngdòng:'bad wine'.European pronunciation.

Warning: Verbally, 酮 ('ketone') and 铜 ('copper') are both pronounced tóng and are indistinguishable. In modern times, new chemical terminology is chosen to avoid conflicts like this.

alkanewán 'complete'wánfireFrom 完 wán 'complete', referring to its saturation, cf. names for alkenes and alkynes
鎓/𬭩 oniumwēng 'old man'wēngspadeEuropean pronunciation. Used in cases when a specific 'onium' character is unavailable or uncommon, e.g., 氧鎓/氧𬭩 yǎngwēng for 'oxonium'.
oxime 'in, on, at'European pronunciation. Formerly known as 胜 shēng, which is also an old variant of 腥 xīng 'rank, strong-smelling', as well as the simplified character for 勝 shèng/shēng 'victory' or 'excel'. Note that 亏 is also the unrelated simplified character for 虧 kuī 'deficit', but in this context, it is the archaic variant character for 于 'in, on, at'.
fluorene 'do not'an edible wild plant
:'dimly' or 'suddenly'
European pronunciation
alkene 'infrequent'the colour of fireFrom 希 'sparse', referring to its unsaturation, cf. names for alkanes and alkynes
酰 (organic or inorganic) acylxiān 'in front'xiānFrom 先 xiān 'earlier [i.e. precursor]', referring to its derivation from acids. Formerly known as 醯 , which also means 'acid, vinegar'.
𨦡 oxoniumyáng 'goat; sheep'yángFrom oxygen, 氧 yǎng
吲哚 indoleyǐn 'attract' and 朵 duǒyǐnduǒTransliteration
indeneyìn 'impression'yìna name of a grassEuropean pronunciation.
steroidzāi 'steroid'zāi.a variant of 災/灾 :zāi: 'calamity'
:'an ancient pottery used for containing wine'
Pictographic in origin, referring to the three side-chains (found in cholesterol) and four rings found in all steroids.
esterzhǐ 'purpose'zhǐFrom 脂 zhī 'lipid', referring to the ester linkages in glycerides. Formerly known as 𨤎 yán.
tropyliumzhuó 'eminent'zhuóEuropean pronunciation
hydrazonezōng 'faction'zōngEuropean pronunciation

Other aspects and examples

In the CCS system, carbon chain lengths are denoted by celestial stems (甲 jiǎ, 乙 , 丙 bǐng, 丁 dīng, 戊 , 己 , 庚 gēng, 辛 xīn, 壬 rén, 癸 guǐ), characters used since the Shang Dynasty (16th-11th centuries BCE) for naming days (and later, to name years). For example, hexane is 己烷 jǐwán, since 己 is the sixth celestial stem. Longer carbon chains are specified by number followed by '碳' tàn 'carbon'. For example, 1-hexadecene is 1-十六碳烯 (read as [1, ] [-, wèi] [十六, shíliù, '16'] [碳, tàn] [烯, ]), where the hyphen is read as 位 (wèi, 'position').

For a more complex example, consider 3-buten-1-ol. Its Chinese name is 3-丁烯-1-醇 (read as [3, sān] [-, wèi] [丁, dīng] [烯, ] [1, ] [-, wèi] [醇, chún]).

The descriptors for degree of substitution, primary, secondary, tertiary, and quaternary, are translated as 伯 (), 仲 (zhòng), 叔 (shū), 季 (), which refer to the first, second, third, and fourth male siblings in a family. For instance, tert-butyllithium is translated as 叔丁基锂 ([叔, shū, 'tert'], [丁, dīng, 'but-'], [基, , 'yl'], [锂, , 'lithium']). Other commonly used isomeric descriptors normal-, iso-, and neo- are translated as 正 (zhèng, 'proper'), 异 (, 'different'), and 新 (xīn, 'new'), respectively.

The numerical prefix bis- is translated as 双 (shuāng, 'double'), while larger multiplicities are simply given by the Chinese word for the number (e.g., 四 (, 'four') for tetrakis-). For example, tetrakis(triphenylphosphine)palladium is rendered 四(三苯基膦)钯, in which 三苯基膦 is triphenylphosphine and 钯 is palladium. The prefix bi- (for joining of ring systems) is translated as 联 (lián, 'join', 'couple'), as in 联苯 for biphenyl.

The stereochemical descriptors cis- and trans- are translated as 顺 (shùn, 'along') and 反 (fǎn, 'against'). The relational prefixes ortho-, meta-, and para- are translated as 邻 (lín, 'neighboring'), 间 (jiàn, 'between'), and 对 (duì, 'opposing'), respectively.

The structural modification descriptors cyclo-, nor- and homo- are translated as 环 (huán, 'ring'), 降 (jiàng, 'lowered'), and 高 (gāo, 'high'). For example, norbornene is translated as 降冰片烯, in which the trivial name (冰片) for bornyl [literally, camphor] is used. When substitutive nomenclature is used for naming heterocycles, the suffix 杂 (zá, 'mixed') is used in the same way as '-a' in English (as in aza, thia, oxa, etc.). As an example, DABCO (1,4-diazabicylo[2.2.2]octane) is named 1,4-二氮杂二环[2.2.2]辛烷.

The common unsaturated groups allyl and propargyl are translated as 烯丙(基) (xībǐng(jī), 'alkene-prop-(yl)') and 炔丙(基) (qūebǐng(jī), 'alkyne-prop-(yl)'). Thus, using 高 for homo- and 烯丙 for allyl, 3-buten-1-ol is also called 高烯丙醇 (i.e., homoallyl alcohol) in Chinese via semisystematic nomenclature.

The Chinese Wikipedia page may be consulted for further details.

Pseudohalogens

  • The character (, "chlorine") may on occasion mean Cl (one atom), or the bonded pair Cl2 (the molecule, the usual form of chlorine). Likewise in describing pseudohalogens, (qíng) may on occasion mean a single CN cyanide ion (e.g. as in 氰化鉀 (qínghuàjiǎ, potassium cyanide, literally "cyanide-ion transform potassium"), or the bonded pair (CN)2 or NCCN ("cyanogen"). The similar (not identical) character (jīng) means "nitrile".

Thermochemical terminology

Although not substances, the thermochemical concepts entropy and enthalpy were assigned Chinese characters based on similar considerations. The 'fire' radical, 火, is used as the semantic category. The character for entropy, 熵 (pinyin: shāng), is derived from 商 (pinyin: shāng), which means 'quotient' in this context. This recognizes the Clausius equation for the differential change in entropy as the differential heat absorbed divided by the temperature: dS = dQ/T. The character for enthalpy, 焓 (pinyin: hán), is derived from 含 (pinyin: hán), which means 'to contain.' This character phonetically approximates the first syllable of 'enthalpy', and recognizes the definition of enthalpy as heat content.

See also

Notes

  1. There have existed two organizations with that name since 1950, as a consequence of the inconclusive resolution of the Chinese Civil War: one based in Beijing and the other based in Taipei. The organization based in Taipei has changed its English name to Chemical Society Located in Taipei while retaining its Chinese name. Besides the usage of simplified vs. traditional components for characters and slight differences in the rules for heterocyclic nomenclature, the rules adopted by the two organizations do not differ significantly.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.