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nomenclature of organic compounds
2024-08-06
For the chemical discipline mainly engaged in the study of compound molecules, in addition to general chemical terminology, it is also necessary to give each compound molecule its own name, which has exceeded tens of millions and is still increasing day by day. More importantly, such names should show a clear or implicit relationship between the name and the compound structure, which requires the establishment of scientific and systematic naming rules for them.
The Status of Organic Compound Nomenclature Internationally
The International Union of Pure and Applied Chemistry (IUPAC) has established a specialized committee for the naming of organic compounds and proposed the IUPAC Nomenclature of Organic Chemistry, which is constantly being revised and supplemented, and has formed a long-term operational mechanism for addressing naming issues. As a result, this naming system has become the most widely used system in the global organic chemistry community. In addition, there are other systematic naming methods, such as the CAS naming system established by the American Chemical Society for the purpose of indexing Chemical Abstracts, and the naming system developed from the Beilstein Encyclopedia in Germany, but the basic framework of these systems is not much different from IUPAC.
The History, Development Status, and Necessity of Revision of Organic Compound Nomenclature in China
In the past, the chemical community in China has also attached great importance to the formulation of the principles for systematic naming of compounds in Chinese. In 1978, when everything was waiting to be revitalized, the Chinese Chemical Society established the "Organic Chemistry Nomenclature Group" to supplement and revise the 1960 "Principles for Systematic Naming of Organic Chemical Substances". In 1980, the "Principles for Naming Organic Chemistry" (1980) was published and officially approved in 1983. However, in the following 30 years, the discipline of organic chemistry made new leaps in development; Furthermore, due to the fact that the "Principles of Organic Chemistry Nomenclature" (1980) was only a relatively concise version at that time, it was indeed far from meeting the needs of the development of organic chemistry today, which brought many problems to the information exchange and teaching of Chinese organic chemistry. The Organic Chemistry Discipline Group of the Second Chemical Terminology Review Committee, established by the National Science and Technology Terminology Review Committee and the Chinese Chemical Society, began exploring the updating and revision of the "Organic Chemistry Naming Principles" (1980) after reviewing the terminology.
Principles of Organic Chemistry Naming (1980)
Considering that when the "Principles of Organic Chemistry Nomenclature" (1980) was formulated in 1983, although it referred to the Blue Book of Organic Chemistry Nomenclature published by the IUPAC Organic Chemistry Nomenclature Committee in 1979, the Blue Book was relatively simple and some of the concepts and formulations used for naming internationally at that time had not yet been mentioned. The "Organic Chemistry Naming Principles" (1980) have provided regulations for the use of some Chinese characters in naming, but some formulations still need to be revised or clarified, and some linking characters required in Chinese naming need to be added.
The basic idea of this revision is that the naming of organic compounds in Chinese should be consistent with the current international naming conventions in basic principles, and the content should roughly cover the Blue Book of Organic Chemistry Naming published by IUPAC in 1979, the Naming Guidelines published in 1993, and the suggestions for naming organic compounds officially published on its website so far. At the same time, appropriate reference should also be made to the IUPAC Preferred Names Naming Suggestions for Organic Compounds published on its website in 2004 (preview draft), and the Nomenclature of Organic Chemistry - IUPAC Recommendations and Preferred Names 2013 officially published by the Royal Society of Chemistry in the name of the new version of the Blue Book 10 years later; In terms of form, it conforms to the habits of Chinese word formation and is easy to convert with English, making it convenient for international communication; For the regulations already made in the 1980 version, the Chinese translated names and characters used should be changed as little as possible, but some rules and characters that are not precise enough still need to be carefully revised. Main content and explanation of revision
This revision mainly refers to the naming guidelines recommended by IUPAC in 1993, and has been supplemented on this basis, especially with significant expansion of the polycyclic parent hydride section. In addition, we have added the natural product section that was already in our 1980 version and added content. Due to the fact that the "Naming Principles" do not involve other terms in organic chemistry, it is referred to as the "Organic Compound Naming Principles" based on the names recommended by IUPAC in 1993. After the 1980s, IUPAC made some significant changes in the arrangement and description of naming rules for organic compounds, mainly including: unifying the naming of carbon hydrides and other heteroatom hydrides under the name of parent hydride; Replace functional groups with characteristic groups. Therefore, in this revision of Chinese naming, we have also made corresponding changes, but due to the small difference in meaning between characteristic groups and functional groups, and the fact that the organic chemistry community has become accustomed to the name functional group, we still retain the use of both at the same time.
When combining various structures to form names in Chinese organic compound names, various linking characters need to be used to express their interrelationships, which is different from English where letters, especially vowels, can be used to express them
Another issue to consider when converting the naming of organic compounds between Chinese and English is the order of substituents in the prefix. In the 1980 version of the naming principles, the names of each substituent are arranged in descending order according to their stereochemical order rules. However, in IUPAC English naming, the names of each substituent are arranged in alphabetical order. Due to the difficulty in determining the size of substituents, especially multi bond substituents, according to stereochemical order rules, and the fact that this arrangement sometimes involves positional numbering in naming, it is recommended to adopt IUPAC's alphabetical order in this revision. Similar sorting problems also exist in the arrangement of multiple complexes in a fused ring and the arrangement of each helical ring in a multi helix ring. This revision suggests adopting the IUPAC approach.
For 3-10 membered monocyclic compounds containing heteroatoms, in addition to their common names, the extended Hantzsch Widman heterocyclic nomenclature system is used in English, which is widely used in English literature. However, there was no corresponding treatment for this naming system in the 1980 edition. In fact, the Chinese literature originated from this naming system, which refers to the widespread use of nitrogen-containing six membered ring triazines, oxygen-containing saturated six membered ring alkanes, and nitrogen-containing five membered ring azoles. Therefore, in this revision, in addition to retaining the above three characters, a unified regulation corresponding to the Hantzsch Widman heterocyclic naming system was made for other 3-10 membered heterocycles, using the characters "cyclopropane 熳" to "cyclodec 熳" to represent the 3-10 membered ring with the maximum cumulative double bond number, and then adding the character "za" to the name of the heteroatom. The saturated ring was indicated by the cyclic ring in the system naming system; In addition, the use of sulfur to represent sulfur impurities and oxygen impurities has also been widely adopted, and it is recommended to continue using them.
Phanes "is a class name for a complex ring system recommended by IUPAC in 1998. The term" cyclophane "has already appeared in literature and can be found in the naming guidelines recommended by IUPAC in 1993. In 1991, the Chinese Chemical Nomenclature Review Committee translated it as" cycloaromatic "or" cyclophane ". The Tibetan naming convention is a relatively simple and clear naming method, involving not only cyclic chain systems, but also not limited to the aromatic ring chain system implied by the Chinese word "cyclic aromatic". Therefore, in Chapter 3 of the book, the content of "3.9 Tibetan mother hydride" was added.
For revisions to other Chinese characters, such as the use of phosphine, arsine, etc., and the different meanings of ketones in the two naming methods, please refer to the relevant sections.
The naming conventions for certain types of compounds, such as rotaxanes, fullerenes, etc., have been suggested by IUPAC but have not been included in this revised draft due to their limited usage. The naming of boron compounds generally belongs to the naming rules for inorganic compounds, so it was not included in this study.
Finally, it must be noted that the "naming principle" refers to the suggested names for various categories of organic compound structures, but they may not necessarily be the unique names of the structures. There may also be common names, semi common names, or other different names obtained from different naming approaches. IUPAC proposed the terms "preferred IUPAC name (PIN)" and "general IUPAC name" in the "Organic Compound Naming Recommendations (Preview)" published on its website in 2004 and the Blue Book officially published 10 years later. However, regardless of the naming method, the structure represented by the compound name should be unique.
The revision of the Naming Principles for Organic Compounds was specially organized and implemented by the Chinese Chemical Society, which was supported by the National Natural Science Foundation of China, the National Science and Technology Terminology Commission and the Chinese Academy of Sciences Shanghai Institute of Organic Chemistry. The revision working group of Naming Principles for Organic Compounds headed by Wu Yulin, a researcher from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, was responsible for drafting the first draft. The first draft was published online for comments, and was reviewed at multiple levels and in different scopes. The final draft was revised - re reviewed - re revised according to opinions. Despite such repeated revisions, the structural types of organic compounds are very complex, and it is inevitable that there are still many named expressions that have not been properly handled. Therefore, we sincerely welcome readers to criticize and correct us. With the development of organic chemistry, the naming principles of organic compounds need to be continuously revised and updated, and the scope involved will also be further expanded. It is recommended to establish a long-term operating mechanism and regularly revise and supplement the "Organic Compound Naming Principles".
The "Principles for Naming Organic Compounds 2017" is a supplementary and revised version of the "Principles for Naming Organic Chemistry" (1980) published by the Chinese Chemical Society in 1983. The book mainly refers to the naming principles recommended by the International Union of Pure and Applied Chemistry (IUPAC) over the years, and combines the habits of Chinese word formation to revise the principles of Chinese systematic naming of organic compounds, adding content on naming various types of organic compound structures, especially expanding the chapter on naming major natural products. The whole book highlights the naming rules for use case explanations and adopts a bilingual naming convention in Chinese and English to facilitate understanding and international communication.
The Status of Organic Compound Nomenclature Internationally
The International Union of Pure and Applied Chemistry (IUPAC) has established a specialized committee for the naming of organic compounds and proposed the IUPAC Nomenclature of Organic Chemistry, which is constantly being revised and supplemented, and has formed a long-term operational mechanism for addressing naming issues. As a result, this naming system has become the most widely used system in the global organic chemistry community. In addition, there are other systematic naming methods, such as the CAS naming system established by the American Chemical Society for the purpose of indexing Chemical Abstracts, and the naming system developed from the Beilstein Encyclopedia in Germany, but the basic framework of these systems is not much different from IUPAC.
The History, Development Status, and Necessity of Revision of Organic Compound Nomenclature in China
In the past, the chemical community in China has also attached great importance to the formulation of the principles for systematic naming of compounds in Chinese. In 1978, when everything was waiting to be revitalized, the Chinese Chemical Society established the "Organic Chemistry Nomenclature Group" to supplement and revise the 1960 "Principles for Systematic Naming of Organic Chemical Substances". In 1980, the "Principles for Naming Organic Chemistry" (1980) was published and officially approved in 1983. However, in the following 30 years, the discipline of organic chemistry made new leaps in development; Furthermore, due to the fact that the "Principles of Organic Chemistry Nomenclature" (1980) was only a relatively concise version at that time, it was indeed far from meeting the needs of the development of organic chemistry today, which brought many problems to the information exchange and teaching of Chinese organic chemistry. The Organic Chemistry Discipline Group of the Second Chemical Terminology Review Committee, established by the National Science and Technology Terminology Review Committee and the Chinese Chemical Society, began exploring the updating and revision of the "Organic Chemistry Naming Principles" (1980) after reviewing the terminology.
Principles of Organic Chemistry Naming (1980)
Considering that when the "Principles of Organic Chemistry Nomenclature" (1980) was formulated in 1983, although it referred to the Blue Book of Organic Chemistry Nomenclature published by the IUPAC Organic Chemistry Nomenclature Committee in 1979, the Blue Book was relatively simple and some of the concepts and formulations used for naming internationally at that time had not yet been mentioned. The "Organic Chemistry Naming Principles" (1980) have provided regulations for the use of some Chinese characters in naming, but some formulations still need to be revised or clarified, and some linking characters required in Chinese naming need to be added.
The basic idea of this revision is that the naming of organic compounds in Chinese should be consistent with the current international naming conventions in basic principles, and the content should roughly cover the Blue Book of Organic Chemistry Naming published by IUPAC in 1979, the Naming Guidelines published in 1993, and the suggestions for naming organic compounds officially published on its website so far. At the same time, appropriate reference should also be made to the IUPAC Preferred Names Naming Suggestions for Organic Compounds published on its website in 2004 (preview draft), and the Nomenclature of Organic Chemistry - IUPAC Recommendations and Preferred Names 2013 officially published by the Royal Society of Chemistry in the name of the new version of the Blue Book 10 years later; In terms of form, it conforms to the habits of Chinese word formation and is easy to convert with English, making it convenient for international communication; For the regulations already made in the 1980 version, the Chinese translated names and characters used should be changed as little as possible, but some rules and characters that are not precise enough still need to be carefully revised. Main content and explanation of revision
This revision mainly refers to the naming guidelines recommended by IUPAC in 1993, and has been supplemented on this basis, especially with significant expansion of the polycyclic parent hydride section. In addition, we have added the natural product section that was already in our 1980 version and added content. Due to the fact that the "Naming Principles" do not involve other terms in organic chemistry, it is referred to as the "Organic Compound Naming Principles" based on the names recommended by IUPAC in 1993. After the 1980s, IUPAC made some significant changes in the arrangement and description of naming rules for organic compounds, mainly including: unifying the naming of carbon hydrides and other heteroatom hydrides under the name of parent hydride; Replace functional groups with characteristic groups. Therefore, in this revision of Chinese naming, we have also made corresponding changes, but due to the small difference in meaning between characteristic groups and functional groups, and the fact that the organic chemistry community has become accustomed to the name functional group, we still retain the use of both at the same time.
When combining various structures to form names in Chinese organic compound names, various linking characters need to be used to express their interrelationships, which is different from English where letters, especially vowels, can be used to express them
Another issue to consider when converting the naming of organic compounds between Chinese and English is the order of substituents in the prefix. In the 1980 version of the naming principles, the names of each substituent are arranged in descending order according to their stereochemical order rules. However, in IUPAC English naming, the names of each substituent are arranged in alphabetical order. Due to the difficulty in determining the size of substituents, especially multi bond substituents, according to stereochemical order rules, and the fact that this arrangement sometimes involves positional numbering in naming, it is recommended to adopt IUPAC's alphabetical order in this revision. Similar sorting problems also exist in the arrangement of multiple complexes in a fused ring and the arrangement of each helical ring in a multi helix ring. This revision suggests adopting the IUPAC approach.
For 3-10 membered monocyclic compounds containing heteroatoms, in addition to their common names, the extended Hantzsch Widman heterocyclic nomenclature system is used in English, which is widely used in English literature. However, there was no corresponding treatment for this naming system in the 1980 edition. In fact, the Chinese literature originated from this naming system, which refers to the widespread use of nitrogen-containing six membered ring triazines, oxygen-containing saturated six membered ring alkanes, and nitrogen-containing five membered ring azoles. Therefore, in this revision, in addition to retaining the above three characters, a unified regulation corresponding to the Hantzsch Widman heterocyclic naming system was made for other 3-10 membered heterocycles, using the characters "cyclopropane 熳" to "cyclodec 熳" to represent the 3-10 membered ring with the maximum cumulative double bond number, and then adding the character "za" to the name of the heteroatom. The saturated ring was indicated by the cyclic ring in the system naming system; In addition, the use of sulfur to represent sulfur impurities and oxygen impurities has also been widely adopted, and it is recommended to continue using them.
Phanes "is a class name for a complex ring system recommended by IUPAC in 1998. The term" cyclophane "has already appeared in literature and can be found in the naming guidelines recommended by IUPAC in 1993. In 1991, the Chinese Chemical Nomenclature Review Committee translated it as" cycloaromatic "or" cyclophane ". The Tibetan naming convention is a relatively simple and clear naming method, involving not only cyclic chain systems, but also not limited to the aromatic ring chain system implied by the Chinese word "cyclic aromatic". Therefore, in Chapter 3 of the book, the content of "3.9 Tibetan mother hydride" was added.
For revisions to other Chinese characters, such as the use of phosphine, arsine, etc., and the different meanings of ketones in the two naming methods, please refer to the relevant sections.
The naming conventions for certain types of compounds, such as rotaxanes, fullerenes, etc., have been suggested by IUPAC but have not been included in this revised draft due to their limited usage. The naming of boron compounds generally belongs to the naming rules for inorganic compounds, so it was not included in this study.
Finally, it must be noted that the "naming principle" refers to the suggested names for various categories of organic compound structures, but they may not necessarily be the unique names of the structures. There may also be common names, semi common names, or other different names obtained from different naming approaches. IUPAC proposed the terms "preferred IUPAC name (PIN)" and "general IUPAC name" in the "Organic Compound Naming Recommendations (Preview)" published on its website in 2004 and the Blue Book officially published 10 years later. However, regardless of the naming method, the structure represented by the compound name should be unique.
The revision of the Naming Principles for Organic Compounds was specially organized and implemented by the Chinese Chemical Society, which was supported by the National Natural Science Foundation of China, the National Science and Technology Terminology Commission and the Chinese Academy of Sciences Shanghai Institute of Organic Chemistry. The revision working group of Naming Principles for Organic Compounds headed by Wu Yulin, a researcher from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, was responsible for drafting the first draft. The first draft was published online for comments, and was reviewed at multiple levels and in different scopes. The final draft was revised - re reviewed - re revised according to opinions. Despite such repeated revisions, the structural types of organic compounds are very complex, and it is inevitable that there are still many named expressions that have not been properly handled. Therefore, we sincerely welcome readers to criticize and correct us. With the development of organic chemistry, the naming principles of organic compounds need to be continuously revised and updated, and the scope involved will also be further expanded. It is recommended to establish a long-term operating mechanism and regularly revise and supplement the "Organic Compound Naming Principles".
The "Principles for Naming Organic Compounds 2017" is a supplementary and revised version of the "Principles for Naming Organic Chemistry" (1980) published by the Chinese Chemical Society in 1983. The book mainly refers to the naming principles recommended by the International Union of Pure and Applied Chemistry (IUPAC) over the years, and combines the habits of Chinese word formation to revise the principles of Chinese systematic naming of organic compounds, adding content on naming various types of organic compound structures, especially expanding the chapter on naming major natural products. The whole book highlights the naming rules for use case explanations and adopts a bilingual naming convention in Chinese and English to facilitate understanding and international communication.
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