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Teaching and Learning of Multilingual Chemical Nomenclature with
ACD/NameAndrey Yerin
and all ACD/Labs team developing and supporting nomenclature tools
San Francisco, USA, August 11, 2014
ACS 248th National Meeting
Division of Chemical Education
Nomenclature is Difficult to Learn and Teach
ACD/Labs nomenclature tools are on the market since 1996and in 1997 we got the following e-mail. Really funny but hardly arguable!
We are not exactly ‘IUPAC team’ and we agree that nomenclature is really difficult both to learn and to teach. We are trying to help.
* The actual context was about learning of obsolete‘ferrous’ and ‘ferric’ against ‘iron(II)’ and ‘iron(III)’.
The development of chemical nomenclature is governed by International Union of Pure and Applied Chemistry (IUPAC).
IUPAC Nomenclature
All specific IUPAC recommendations are published in Journal of Pure and Applied Chemistry and freely available.
A collection of main recommendations can be found at www.chem.qmul.ac.uk/iupac hosted by School of Biological and Chemical Sciences, Queen Mary University of London.
In additional to specific recommendations IUPAC publishes books for all areas of chemical nomenclature. The books can be purchased but after some period the content can be available free of charge.
www.iupac.orgDivision of Chemical Nomenclature and Structure
Representation (Division VIII)
Learn Nomenclature or Use Programs
As a result a reliable nomenclature knowledge is lacked by all parties—students, teachers and practicing chemists.
The problem is not only that chemists do not know nomenclature well. The real problem is that many chemist still believe they can name chemical substances well.
The problem is that nomenclature publications are aimed at experienced readers. There is significant gap between educational resources and actual nomenclature recommendations.
According to investigation performed in 2005 about 25% of names in journals were wrong.
G. A. Eller, Molecules, 2006, 11, 915-928
Computer naming programs already exceed the knowledge of most chemists and do not make misprints that are so common for human beings.
Algorithmic Name Generation
Nomenclature software entered the market more than 20 years ago.
The programs differ significantly in possibilities but all outperform most chemists.
Naming programs are reliable and deserve integration in education.
Company Program/Tool Released Availability
Beilstein (discontinued) Autonom 1991 freeware/commercial
ACD/Labs ACD/Name 1996 freeware/commercial
ChemInnovation Software Nomenclator 1996 commercial
Chem Draw Name=Struct 2003 commercial
OpenEye Lexichem 2005 freeware/commercial
ChemAxon IUPAC name 2007 freeware/commercial
ACD/Labs Nomenclature Tools
ACD/Name is well recognized as the most advanced naming program supporting IUPAC nomenclature.
It is very important in this context that ACD/Name was developed keeping educational needs in mind—it is not just chemical name generation but explanation as well.
ACD/Labs has been developing nomenclature products for about 20 years.
1994 The beginning—the idea and first procedures
1996 First commercial version of ACD/Name—naming in English
1999 Generation of chemical structures from names—ACD/Name to Structure
2005 Name generation in French and German
2010 Name generation in Danish, Finnish, Italian, Netherlands, Portuguese, Spanish and Swedish
2014 New IUPAC rules and probably more languages expected
ACD/Name Tools
Just draw a structure and push the button to get the chemical name.
Names can be generated for most classes of organic compounds in full accordance with IUPAC recommendations.
ACD/Name tools
IUPAC numbering can be shown
The display of numbering scheme allows to understand the locants for substituents and functional groups
ACD/Name Tools
Name fragments are associated with the structure fragments.
Pointing at any part of a name or structure allows you to understand the structure to name relationship.
ACD/Name Tools
Name segments are explained with the corresponding IUPAC rules.
Name segments are classified by their role in chemical names.
ACD/Name Tools
Full text of IUPAC recommendations is provided.
The links allow you to access any specific rule defining the naming principles for specific segments.
ACD/Name Tools
Stereodescriptors are generated and explained.
An assignment of each stereodescriptor is explained with a hierarchical graph to conclude the seniority of ligands.
ACD/Name Tools
Supports not only most classes of organic compounds but biochemicalsand some inorganic compounds also.
Thus, being powerful for scientific and industrial use, the program retains high value for all levels of chemical education.
Nomenclature in Other Languages
All IUPAC recommendations are developed and published in English
The adaptation of English nomenclature is a responsibility of the corresponding national nomenclature committees, if existing, or groups of enthusiastic chemists with a good knowledge of nomenclature
For some languages practically all IUPAC recommendations are translated and published. For example, German and Portuguese. For other languages such translations are scarce and often outdated. For example, Spanish and Italian.
Surprisingly, you can find the translation of some major recommendations in Macedonian but not in Spanish. While more than 400 M speak Spanish and just 2 M Macedonian.
That is why for some languages there is no agreement on how to name specific classes of chemicals. Even for basic educational resources.
Nomenclature in Other Languages
It takes significant time to translate and publish. Chemists need to wait years to follow actual nomenclature.
English 1993
It means that nomenclature conventions in some languages can fall behind in decades!
Portuguese 2002Czech 2000
Algorithmic name generation can help here as well if naming in other languages is supported.
New IUPAC Organic Nomenclature
In December 2013, the book “Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names” was published.
It is truly a long awaited publication.The work started in 1992. The IUPAC project was initiated in 2001.
This major organic nomenclature publication is an answer to the rapid development of chemistry and appearance of new classes of chemicals we have seen over the past 20 years.
The book deals with naming principles that were unchanged for about 35 years since the IUPAC Blue book was published in 1979.
Nomenclature in Multilingual World
The availability and development of nomenclature resources inspecific language depends on:
• Speaking population and hence a number of chemists
o 500 M English, 100 M German and 5 M Finnish
• Teaching and learning chemistry in specific language
o Ireland is close in population to Finland but in Ireland chemistry is taught in English
• Degree of development of chemical nomenclature
o For some languages official recommendations do not exist. What to choose from existing variations?
• The language specific complexity of chemical nomenclature
o Chemical names share the language grammar and some languages are more difficult than others. This primarily concerns languages with inflection of nouns and adjectives according to grammatical gender and case.
Nomenclature and Languages
Learning of nomenclature requires the memorization of a lot of names.
According to our estimations about 1000 specific names.
DA: ethan octan pyridin naphthalen
DE: Ethan Octan Pyridin Naphthalin
EN: ethane octane pyridine naphthalene
ES: etano octano piridina naftaleno
FI: etaani oktaani pyridiini naftaleeni
FR: éthane octane pyridine naphtalène
IT: etano ottano piridina naftalene
NL: ethaan octaan pyridine naftaleen
PT: etano octano piridina naftaleno
SV: etan oktan pyridin naftalen
NCH3
CH3
CH3 CH3
Nomenclature and Languages
Chemical name follows the language grammar, for example, Latin and Germanic groups.
These two groups have rather simple grammar with practically no inflection.
DA: butansyre methylbenzoat
DE: Butansäure Methylbenzoat
EN: butanoic acid methyl benzoate
ES: ácido butanoico benzoato de metilo
FI: butaanihappo metyylibentsoaatti
FR: acide butanoique benzoate de méthyle
IT: acido butanoico benzoato di metile
NL: butaanzuur methylbenzoaat
PT: ácido butanóico benzoato de metilo
SV: butansyra metylbensoat
O
O CH3CH3
O
OH
Nomenclature and Languages
English language and Germanic group lack any inflection.
Latin group languages have inflection, while minimal. For example in Italian:
All these specific procedures can be implemented in a program.
sodium acetate silver acetate pyridine acetate
οξικό νάτριο οξικός άργυρος οξική πυριδίνη
sodium - neutral silver - masculine pyridine - feminine
acetic acid acetic anhydride
acido acetico anidride acetica
acido - masculine anidride - feminine
The heaviest inflection exists in Greek, Slavic and Baltic languages.
Nomenclature and Languages
Alphabetization of substituents
Track how a specific substituent migrates within the name.
DA: 2-chlor-5-methoxy-3-methyl-4-phenylcyclohexanol
DE: 2-Chlor-5-methoxy-3-methyl-4-phenylcyclohexanol
EN: 2-chloro-5-methoxy-3-methyl-4-phenylcyclohexanol
ES: 2-cloro-4-fenil-3-metil-5-metoxiciclohexanol
FI: 4-fenyyli-2-kloori-5-metoksi-3-metyylisykloheksanoli
FR: 2-chloro-5-méthoxy-3-méthyl-4-phénylcyclohexanol
IT: 2-cloro-4-fenil-3-metil-5-metossicicloesanolo
NL: 2-chloor-4-fenyl-5-methoxy-3-methylcyclohexanol
PT: 2-cloro-4-fenil-3-metil-5-metoxiciclohexanol
SV: 4-fenyl-2-kloro-5-metoxi-3-metylcyklohexanol
OH
ClCH3
OCH3
Nomenclature and Languages
Renumbering due to different alphabetical order.
Sometimes substituents have different locants due to different alphabetical order in the name.
5
6
4
N1
3
2
CH3 Ph
3
2
4
N1
5
6
CH3 Ph
DA: 2-methyl-6-phenylpyridin ES: 2-fenil-6-metilpiridina
DE: 2-Methyl-6-phenylpyridin FI: 2-fenyyli-6-metyylipyridiini
EN: 2-methyl-6-phenylpyridine IT: 2-fenil-6-metilpiridina
FR: 2-méthyl-6-phénylpyridine NL: 2-fenyl-6-methylpyridine
PT: 2-fenil-6-metilpiridina
SV 2-fenyl-6-metylpyridi
ACD/Labs multilingual naming was inspired by the contract with European Commission Taxation and Customs Union aimed at developing procedures for translation from English to other European languages.
ACD/Name and Languages
The current version of ACD/Name supports naming in 10 languages
Aside from some small language specific issues the program correctly names most chemical substances, especially organic.
ACD/Name exceeds the nomenclature knowledge of most professional chemists and educators.
ACD/Name and Languages
It is possible to select only one specific language or to select English together with any other to learn the differences.
Changing the naming preferences allows the user to see both systematic and trivial names together.
ACD/Name – Additional Languages
We are going to extend naming to more languages
ACD/Name supports 16 languages in our internal version, compared to 10 available in the official version and we continue to add even more.
The development is not so quick due to difficulties to find reliable sources of nomenclature rules for specific languages and a lot of basic translations to collect.We gladly accept any help in finding the sources of names in specific language.
This work is under way and new languages will appear in ACD/Name in future versions.
ACD/Labs Naming Tools
Program Features
ChemSketch Name Free Free, 50 atoms only, English only*
ACD/Name Chemist Version Names only, all supported languages
ACD/Name Full featured
ACD/Name Batch Treatment of large structure sets
ACD/I-Lab Web-based, English only *, Free also
ACD/Labs produces several name generation tools.
We expect to release the new version ACD/Name with support of new IUPAC rules by the end of 2014.Additional languages will appear soon.
* We are considering the addition of multilingual naming
Conclusion Remarks
• Extend nomenclature teaching
o Should not be restricted by basic principles
• Consult available IUPAC nomenclature resources
o Essentials of inorganic and organic nomenclatures are expectedsoon
• Use available software tools
o Programs can help significantly in nomenclature learning andteaching
• Programming of nomenclature is a kind of science
o ACD/Labs team is proud of our achievements in this area andcontinues nomenclature-related work
Thank you
