Organic nomenclature in Chinese
The
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
Table
Below is a table, in
Character | Phonetic | Pronunciation | Other meanings | Origin/Notes |
---|---|---|---|---|
胺 amine | 安 ān 'peace' | àn | è (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. |
薁 azulene | 奥 ào 'mysterious' | ào | yù: wild grapes | European pronunciation |
苯 phenyl |
本 běn 'this','root' | běn | the appearance of grass growing | European pronunciation |
吡啶 pyridine | 比 bǐ 'compare' and 定 dìng 'stability' | bǐdìng | 'slander' or 'compare' bì : bird onomatopoeia |
Transliteration |
吡咯 pyrrole | 比 bǐ 'compare' and 各 gè 'each' | bǐluò | gē or gé:'cackle', 'cluck', 'this', or 'pickled mustard'; kǎ (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 | 比 bǐ 'compare' and 南 nán 'south' | bǐnán | to transliterate '-ran'. | Transliteration. |
吡喃鎓 pyrylium
|
比 bǐ 'compare', 南 nán 'south', and 翁 wēng 'old man': | bǐnánwēng | Combination of transliteration for 'pyran' and suffix for 'onium'. | |
苄 benzyl |
卞 biàn 'hurried' | biàn | European pronunciation | |
卟吩 porphin |
卜 bǔ 'foretell' and 分 fēn 'divide' | bǔfēn | 卟 as 'jī': 'divination' or 'to consider' 吩 :'to instruct, command'. |
Transliteration. Formerly known as 㗊 léi, which depicts the porphin ring system pictographically. |
醇 alcohol | 享 xiǎng 'enjoy' | chún | (formerly) rich wine | Not newly coined |
噠嗪/哒嗪 pyridazine | 達/达 dá 'arrive at' and 秦 qín ' Qin Dynasty ' |
dāqín | Transliteration. | |
噁唑/𫫇唑 oxazole | 惡/恶 è 'evil' and 坐 zuò 'sit' | èzuò | Transliteration. | |
苊 acenaphthene | 厄 è 'hardship' | è | European pronunciation | |
蒽 anthracene | 恩 ēn 'favor' | ēn | a name of a grass | European pronunciation. |
菲 phenanthrene | 非 fēi 'not' | fēi | fragrant fěi:'poor'. |
European pronunciation. |
酚 (also 苯酚) phenol | 分 fēn 'divide' | fēn (běnfēn) | European pronunciation | |
碸/砜 sulfone | 風/风 fēng 'the wind' | fēng | European pronunciation (亞碸/亚砜 yàfēng [lit. minor sulfone], is used for sulfoxide) | |
呋喃 furan | 夫 fū 'husband' and 南 nán 'south' | fūnán | as a variant of 趺: 'back of the foot' or 'to sit cross-legged' 喃:'chattering' or 'to mumble |
Transliteration. |
呋咱 furazan | 夫 fū 'husband' and 自 zì 'self' | fūzán | 咱 :we | Transliteration |
酐 (organic or inorganic) anhydride |
干 gān 'dry' | gān | bitter wine | From (simplified) 干 gān 'dry'. |
苷 glycoside | 甘 gān 'sweet' | gān | 'licorice | From 甘 gān 'sweet'. Formerly known as 甙 dài, composed of 弋 from 代 dài 'substitute' and 甘 gān 'sweet'. |
胍 guanidine | 瓜 guā 'melon' | guā | gū: 'large abdomen' or 'stoutness' | European pronunciation |
胲 hydroxylamine | 亥 hài '9-11 pm' | hǎi | gāi:'the flesh where hair grows on the big toe', or 'prepare' gǎi: 'cheek' |
European pronunciation. . |
磺 sulfonyl |
黃/黄 huáng 'yellow' | huáng | From 硫磺 liúhuáng 'sulfur'; e.g., 磺胺 huáng'àn (Taiwan huáng'ān) is sulfonamide | |
腈 nitrile | 青 qīng 'blue', 'green' | jīng | pure meat | From cyanogen, 氰 qíng (Taiwan qīng), itself derived from 青 qīng, blue/green/cyan, cf. Prussian blue |
肼 hydrazine | 井 jǐng 'a well' | jǐng' | European pronunciation | |
胩 isonitrile |
卡 kǎ 'stop','check' | kǎ | From older nomenclature carbylamine (Also known as 異腈/异腈 yìjīng [lit. different nitrile])
| |
蒈 carane | 皆 jiē 'all' | kǎi | European pronunciation | |
莰 camphane |
坎 kǎn 'threshold' | kǎn | European pronunciation | |
喹啉 quinoline | 奎 kuí 'stride' and 林 lín 'forest' | kuílín | 啉: lán: 'greed', 'drink a round of wine', 'finish drinking' or 'piercing noise' lìn or làn: 'stupid'. |
Transliteration. |
醌 quinone | 昆 kūn 'elder brother' | kūn | European pronunciation | |
膦 phosphine | 粦 lín | lìn | liǎn: '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. |
醚 ether | 迷 mí 'bewilder' | mí | drunk | From 迷 mí 'confusion', from anesthetic properties of diethyl ether. |
熳 mancude | 曼 màn 'graceful' | màn | European 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, ...). | |
脒 amidine | 米 mǐ 'rice' | mǐ | European pronunciation | |
咪唑 imidazole | 米 mǐ 'rice' and 坐 zuò 'sit' | mǐzuò | 咪: mī: onomatopoeia for cats or used to describe the appearance of a smile. | Transliteration. |
嘧啶 pyrimidine | 密 mì 'dense' and 定 dìng 'stability' | mìdìng | Transliteration | |
萘 naphthalene | 奈 nài 'persevere' | nài | European pronunciation | |
脲 urea | 尿 niào 'urine' | niào | From 尿 niào 'urine' | |
薴/苧 limonene | 寧/宁 níng 'peaceful' | níng | 薴: messy | From 檸檬/柠檬 níngméng 'lemon' |
哌啶 piperidine | 𠂢 pài and 定 dìng 'stability' | pàidìng | Transliteration | |
哌嗪 piperazine | 𠂢 pài and 秦 qín ' Qin Dynasty ' |
pàiqín | Transliteration | |
蒎 pinene | 派 pài 'assign' | pài | European pronunciation | |
苉 picene | 匹 pǐ 'equal' | pǐ | European pronunciation | |
嘌呤 purine | 票 piào '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 hydroxyl |
羊 yáng 'sheep' and 巠/𢀖 jīng | qiǎng | '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' | qiú | From fusion of the sounds of 氫/氢 qīng 'hydrogen' and 硫 liú 'sulfur' (Sulfonium is 鋶/锍 liǔ, in analogy with ammonium) | |
醛 aldehyde | 荃 quán | quán | 'change in the flavour of wine' or 'pickled vegetables'. | From 荃 quán, a type of fragrant grass, referring to the fragrance of many aldehydes. |
炔 alkyne | 夬 guǎi | quē | guì: a surname, or 'the appearance of smoke' | From 缺 quē 'deficient', referring to its unsaturation, cf. names for alkenes . Pronounced as jué in Taiwan. .
|
脎 osazone | 杀 shā 'kill' | sà | European pronunciation | |
噻唑 thiazole | 塞 sāi 'to stop up' and 坐 zuò 'sit' | sāizuò | European pronunciation | |
胂 arsine | 申 shēn '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, qūn | suān | sour | Not newly coined |
羧 carboxyl |
n.a. | suō | zuī: woollen knitwear | Character construction is based on combination of 氧 yǎng 'oxygen' and 酸 suān 'acid', pronunciation from European pronunciation. |
肽 peptide | 太 tài 'excessively' | tài | European pronunciation | |
酞 phthalein |
太 tài 'excessively' | tài | European pronunciation | |
羰 carbonyl |
羊 yáng 'sheep' and 炭 tàn 'charcoal' | tāng | From fusion of the sounds of 氧 yǎng 'oxygen' and 碳 tàn 'carbon'. Pronounced as tàn in Taiwan. | |
萜 terpene | 帖 tiè 'obedient' | tiē | European pronunciation | |
烴/烃 hydrocarbon | 巠/𢀖 jīng | tīng | jǐng: 'warm', 'burnt smell' or 'the appearance of burning' | From fusion of the sounds of 碳 tàn 'carbon' and 氫/氢 qīng 'hydrogen'. |
酮 ketone | 同 tóng 'same' | tóng | dòng:'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. |
烷 alkane | 完 wán 'complete' | wán | fire | From 完 wán 'complete', referring to its saturation, cf. names for alkynes
|
鎓/𬭩 onium | 翁 wēng 'old man' | wēng | spade | European pronunciation. Used in cases when a specific 'onium' character is unavailable or uncommon, e.g., 氧鎓/氧𬭩 yǎngwēng for 'oxonium'. |
肟 oxime | 亏 yú 'in, on, at' | wò | 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 yú 'in, on, at'. | |
芴 fluorene | 勿 wù 'do not' | wù | an edible wild plant hū:'dimly' or 'suddenly' |
European pronunciation |
烯 alkene | 希 xī 'infrequent' | xī | the colour of fire | From 希 xī 'sparse', referring to its unsaturation, cf. names for alkynes
|
酰 (organic or inorganic) acyl |
先 xiān 'in front' | xiān | From 先 xiān 'earlier [i.e. precursor]', referring to its derivation from acids. Formerly known as 醯 xī, which also means 'acid, vinegar'. | |
𨦡 oxonium | 羊 yáng 'goat; sheep' | yáng | From oxygen, 氧 yǎng | |
吲哚 indole | 引 yǐn 'attract' and 朵 duǒ | yǐnduǒ | Transliteration | |
茚 indene | 印 yìn 'impression' | yìn | a name of a grass | European pronunciation. |
甾 steroid | 甾 zāi 'steroid' | zāi | .a variant of 災/灾 :zāi: 'calamity' zī:'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. |
酯 ester | 旨 zhǐ 'purpose' | zhǐ | From 脂 zhī 'lipid', referring to the ester linkages in glycerides . Formerly known as 𨤎 yán.
| |
䓬 tropylium |
卓 zhuó 'eminent' | zhuó | European pronunciation | |
腙 hydrazone | 宗 zōng 'faction' | zōng | European pronunciation |
Other aspects and examples
In the CCS system, carbon chain lengths are denoted by
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, xī] [1, yī] [-, wèi] [醇, chún]).
The descriptors for degree of substitution, primary, secondary, tertiary, and quaternary, are translated as 伯 (bó), 仲 (zhòng), 叔 (shū), 季 (jì), 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, jī, 'yl'], [锂, lǐ, 'lithium']). Other commonly used isomeric descriptors normal-, iso-, and neo- are translated as 正 (zhèng, 'proper'), 异 (yì, '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 (sì, '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
The Chinese Wikipedia page may be consulted for further details.
Pseudohalogens
- The character 氯 ( lǜ, "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 腈 (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
- 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.