Demos > IUPAC Naming

⚠
For unrestricted access to this online tool, please log into ChemDoodle Mobile in your browser using your ChemDoodle license. ChemDoodle licenses may be obtained in our store, which will also give you access to our desktop software: ChemDoodle 2D and ChemDoodle 3D.

Use this tool to either convert drawn chemical structures into IUPAC names or to create the chemical structure from the written IUPAC name. Please read the instructions below each input. The number of free calls to this function is limited. For unlimited IUPAC naming with dozens of options, use ChemDoodle 2D, or ask your institution to obtain a ChemDoodle site license so you may have free access.

  • Structure to Name
  • Name to Structure
    Read IUPAC Name

    Instructions

    Greek Characters
    Greek characters may be specified by:

    1. The appropriate Unicode character e.g. &lambda
    2. The romanised name for the letter e.g. lambda
    3. The romanised name for the letter surrounded by dots e.g. .lambda.
    4. The corresponding modern letter prefixed with a dollar e.g. $l

    Super scripts
    Super scripts may be specified by:

    1. A carat with bracketing e.g. N^(2)
    2. A carat e.g. N^2
    3. Bracketing e.g. N(2)
    4. Using tildes e.g. N~2~
    5. Using stars e.g. N*2*
    6. Using angle brackets e.g. N<2>

    Note that for locants, the algorithm will be able to disambiguate that N2 means N^2 and for von Baeyer systems the algorithm will intelligently guess what should have been superscripted.

    For spiro systems, indication of superscripts is required.

    Example IUPAC Names

    Click to load into the above text area.

    1. Pentane
    2. Butanal
    3. Benzene
    4. Bis(2-naphthyl)methane
    5. 2,3-Xylenol
    6. Pentacyclo[13.7.4.33,8.018,20.113,28]triacontane

    Powered by OPSIN, which is available in ChemDoodle 2D.

Traditional: Methane
Attempted PIN: methane
IUPAC naming is in ChemDoodle 2D
with dozens of options!:
  • Control over "Method A" for functional groups
  • Forcing functional groups as substitutents
  • Disabling functional group base nuclei
  • Toggling "per" nomenclature
  • Display of implied locants
  • Locant positioning
  • Disabling trivial names
  • Various trivial naming options
  • Toggling ortho/meta/para
  • Control over the choice of base nucleus
  • Control over the Hantzsch-Widman system
  • Toggling stereochemistry
  • Toggling "bis" nomenclature
  • Text formatting
  • and more...!

Instructions

IUPAC names can be generated for drawn structures in the sketcher. The name is displayed in large font above the sketcher as you doodle. Please give it a try and let us know if you encounter any issues. Both a traditional IUPAC name and an attempted Preferred IUPAC Name (PIN) are generated. For more information on what these names are, how they are generated, and further options, please see Chapter 14 of the ChemDoodle 2D User Guide. A comparison table for IUPAC naming against two of our competitors is provided below. You can click on any of the images of the molecules to load them into the sketcher for further evaluation.

ChemDoodle®Competitor #1Competitor #2
Bis(2-naphthyl)methane dinaphthalen-2-ylmethane 2-(naphthalen-2-ylmethyl)naphthalene
2(10),3-Pinadiene 6,6-dimethyl-4-methylenebicyclo[3.1.1]hept-2-ene 6,6-dimethyl-4-methylidenebicyclo[3.1.1]hept-2-ene
2,4-Dihydro-1,3-benzodithiin 4H-benzo[d][1,3]dithiine 2,4-dihydro-1,3-benzodithiine
3,6,8-Trioxabicyclo[3.2.2]nonane 3,6,8-trioxabicyclo[3.2.2]nonane 3,6,8-trioxabicyclo[3.2.2]nonane
2,3-Xylenol 2,3-dimethylphenol 2,3-dimethylphenol
1-[p-(3-Hydroxypropyl)phenyl]-1,2-ethanediol 1-(4-(3-hydroxypropyl)phenyl)ethane-1,2-diol 1-[4-(3-hydroxypropyl)phenyl]ethane-1,2-diol
Perfluoro(1-methylperhydronaphthalene) 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)decahydronaphthalene 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene
4-(Isopropylidenehydrazono)-2,5-cyclohexadiene-1-carboxylic acid 4-(propan-2-ylidenehydrazono)cyclohexa-2,5-dienecarboxylic acid 4-[2-(propan-2-ylidene)hydrazin-1- ylidene]cyclohexa-2,5-diene-1-carboxylic acid
1-Ethylidene-5-(2-naphthyl)carbonohydrazide Unable to name. 3-(ethylideneamino)-1-(naphthalen-2-ylamino)urea
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Pentacyclo[13.7.4.33,8.018,20.113,28]triacontane Unable to name. pentacyclo[13.7.4.3³,⁸.0¹⁸,²⁰.1¹³,²⁸]triacontane
5λ6-Thiatrispiro[2.1.1.27.15.25.23]tetradecane Unable to name. 5λ⁶‐thiatrispiro[2.1.1.2⁷.1⁵.2⁵.2³]tetradecane
Trispiro[cyclopentane-1,5'-[1λ4,4]dithiane-2',2''-indan-1',1'''-thiophene] Unable to name. 1'',3''‐dihydro‐1'λ⁴‐trispiro[cyclopentane‐1,5'‐[1,4]dithiane‐2',2''‐indene‐1',1'''‐thiophene]
Tetrastannoxane tetrastannoxane tetrastannoxane
2-Boryltriborane(5) Unable to name. triborylborane
Butyl Unable to name. monobutyl
2,4-Quinolediyl Unable to name. Unable to name.
Tetramethylammonium tetramethylammonium tetramethylazanium
1,4-Dihydro-1,4-naphthalenediide 1,4-dihydronaphthalene-1,4-diide 1,4‐dihydronaphthalene‐1,4‐diide
(Trimethylammonio)acetate 2-(trimethylammonio)acetate 2‐(trimethylazaniumyl)acetate
(1-2H1)Ethanol ethan-1-d-1-ol (1‐2H1)ethan‐1‐ol
1-(Aminomethyl)cyclopentan(18O)ol 1-(aminomethyl)cyclopentan-1-ol-18O 1‐(aminomethyl)cyclopentan‐1‐(¹⁸O)ol
2-Methoxy(3,4,5,6-3H4)phenol 2-methoxyphen-3,4,5,6-t4-ol 2‐methoxy(3H4)phenol
Disodium carbonate Unable to represent. Unable to represent.
Iron(2+) diiron(3+) tetraoxide Unable to represent. Unable to represent.
Hexaamminecobalt(3+) chloride sulfate Unable to represent. Unable to represent.
tetrakis(triphenylphosphanyl)palladium Unable to name. tetrakis(triphenylphosphine)palladium(0)

References

  1. Nomenclature of Organic Chemistry: Sections A, B, C, 3rd ed.; Butterworths: London, 1971.
  2. Rigaudy, J.; Klesney, S. P. Nomenclature of Organic Chemistry: Sections A, B, C, D, E, F and H, 4th ed.; Pergamon Press: Oxford, 1979.
  3. Moss, G. P. Revision of the Extended Hantzsch-Widman System of Nomenclature for Heteromonocycles (Recommendations 1982). Pure Appl. Chem. 1983, 55, 409-416.
  4. Powell, W. H. Treatment of Variable Valence in Organic Nomenclature (Lambda Convention) (Recommendations 1983). Pure Appl. Chem. 1984, 56, 769-778.
  5. Panico, R.; Powell, W. H.; Richer, J. Nomenclature of Organic Chemistry: Recommendatios 1993; Blackwell Scientific Publications: Oxford, 1993.
  6. Moss, G. P. Nomenclature of Fused and Bridged Fused Ring Systems (IUPAC Recommendations 1998). Pure Appl. Chem. 1998, 70, 143-216.
  7. Favre, H. A.; Hellwich, K.; Moss, G. P.; Powell, W. H.; Traynham, J. G. Corrections to A Guide to IUPAC Nomenclature of Organic Compounds (IUPAC Recommendations 1993). Pure Appl. Chem. 1999, 71, 1327-1330.
  8. Moss, G. P. Extension and Revision of the von Baeyer System for Naming Polycyclic Compounds (Including Bicyclic Compounds) (IUPAC Recommendations 1999). Pure Appl. Chem. 1999, 71, 513-529.
  9. Moss, G. P. Extension and Revision of the Nomenclature for Spiro Compounds (Including Bicyclic Compounds) (IUPAC Recommendations 1999). Pure Appl. Chem. 1999, 71, 531-558.
  10. Preferred names in the nomenclature of organic compounds: Draft 7 October 2004; IUPAC, 2004.
  11. Connelly, N. G.; Damhus, T.; Hartshorn, R. M.; Hutton, A. T. Nomenclature of Inorganic Chemistry: IUPAC Recommendations 2005; RSC Publishing: Norfolk, UK, 2005.
  12. Favre, H. A.; Powell, W. H. Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013; Royal Society of Chemistry: Cambridge, 2014.

Get your work done with our popular desktop software.

ChemDoodle 2D
ChemDoodle 3D