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dipolar compounds

Electrically neutral molecules carrying a positive and a negative charge in one of their major canonical descriptions. In most dipolar compounds the charges are delocalized; however the term is also applied to species where this is not the case. 1,2-Dipolar compounds have the opposite charges on adjacent atoms. The term 1,3-dipolar compounds is used for those in which a significant canonical resonance form can be represented by a separation of charge over three atoms (in connection with 1,3-dipolar cycloadditions). Subclasses of 1,3-dipolar compounds include:
  1. Allyl type X=Y+–Z mesomer-arrow X–Y+=Z mesomer-arrow X+–Y–Z mesomer-arrow X=Y–Z+ (X, Z = C, N, or O; Y = N or O)
  2. Propargyl type X≡N+–Z mesomer-arrow X=N+=Z mesomer-arrow X=N–Z+ mesomer-arrow X–N=Z (X = C or O, Z = C, N, or O)
  3. Carbene type X:–C=Z mesomer-arrow X+=C–Z (X = C or N; Z = C, N, or O)
    Source:
    PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1333
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.D01753.
Original PDF version: http://www.iupac.org/goldbook/D01753.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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