Arene substitution patterns

From Wikipedia, the free encyclopedia

(Redirected from Aromatic meta substituent)
Jump to: navigation, search

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.

Contents

Main arene substitution patterns.
Main arene substitution patterns.
  • In ortho-substitution, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked G (for Group) and ortho.
  • In meta-substitution the substituents occupy positions 1 and 3 (corresponding to G and meta in the diagram).
  • In para-substitution, the substituents occupy the opposite ends (positions 1 and 4). The toluidines serve as an example for these three types of substitution.

ipso- substitution.
ipso- substitution.
meso- substitution
meso- substitution
peri- substitution.
peri- substitution.
  • Ipso-substitution describes two substituents sharing the same ring position in an intermediate compound in an electrophilic aromatic substitution.
  • Meso-substitution refers to the substituents occupying a benzylic position. It is observed in compounds such as calixarenes and acridines.
  • Peri-substitution occurs specifically in naphthalenes for substituents at the 1 and 8 positions.

  • In cine-substitution, the entering group takes up a position adjacent to that occupied by the leaving group. For example, cine-substitution is observed in aryne chemistry.
  • Tele-substitution occurs when the new position is more than one atom away on the ring.[1]

The meanings of the prefixes ortho, meta and para are all derived from Greek: respectively meaning straight or correct, following or after and akin to or similar. The relationship to the current meaning is perhaps not obvious. The ortho description was historically used to designate the original compound and an isomer was often called the meta compound. For instance, the trivial names orthophosphoric acid and trimetaphosphoric acid have nothing to do with aromatics at all. Likewise the description para was reserved for just closely related compounds. Thus Berzelius originally called the racemic form of aspartic acid paraaspartic acid (another obsolete term: racemic acid) in 1830. The use of the descriptions ortho, meta and para for multiple substituted aromatic rings starts with Wilhelm Körner in the period 1866–1874 although he chose to reserve the ortho prefix for the 1,4 isomer and the meta prefix for the 1,2-isomer. The current nomenclature (different again from that of Körner) was introduced by the Chemical Society in 1879 [2].

Examples of the use of this nomenclature are given for isomers of cresol:

Cresol isomers

Catechol, resorcinol and hydroquinone are isomers also:

Catechol, resorchinol and hydroquinone

Phthalic acid has two isomers, the meta isomer isophthalic acid and the para isomer terephthalic acid:

Phtalic acid, isophtalic acid, terepthalic acid

  1. ^ Gold Book definitionLink.
  2. ^ The Origins of the Ortho-, Meta-, and Para- Prefixes in Chemical Nomenclature, William B. Jensen, Journal of Chemical Education • Vol. 83 No. 3 March p. 356 2006
Advanced Search
Included Web Search Engines


Safe Search

close

Top Matching Results

Occasionally Search.com will highlight specialized results that are based on the context of your query. Examples of specialized results include specific links to news, images, or video.

Top Matching Results may highlight information from other Search.com pages, content from the CNET Network of sites, or third party content. The listings are based purely on relevance. Search.com does not receive payment for listings in this section but our partners that provide this data may get paid for listing these products.

Sponsored Links

This section contains paid listings which have been purchased by companies that want to have their sites appear for specific search terms and related content. These listings are administered, sorted and maintained by a third party and are not endorsed by Search.com.

Search Results

Search.com sends your search query to several search engines at one time and integrates the results into one list which has been sorted by relevance using Search.com's proprietary algorithm. You can customize the list of search engines included in your metasearch from the preferences.

The search engines that are used in your metasearch may allow companies to pay to have their Web sites included within the results. To view the Paid Inclusion policy for a specific search engine, please visit their Web site. Search.com does not accept payment or share revenue with any search engine partner for listings in this section.